places to visit near woodstock vermont

New England Wanderlust

Fall , Spring , Summer , Vermont , Winter  ·  September 15, 2022

27 Wonderful Things To Do In Woodstock, VT In Every Season (2024)

Woodstock is one of my absolute favorite towns in Vermont to visit, regardless of the season. It’s packed with so much small town, New England charm at every turn, and it offers such a fun variety of things to do. Throw in amazing restaurants and picturesque covered bridges, it’s also one of the best places to visit in New England .

If you’re trying to plan your first trip to Woodstock, you’re in the right place. I’ve visited Woodstock in all the seasons, and I’m thrilled to share with you my top things to do in this cute little town. With that, let’s jump in!

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Is Woodstock, VT Worth Visiting?

Absolutely, and if you’re looking to visit one of the most charming towns in Vermont, Woodstock is the perfect choice. In the main village, you’ll find a lovely covered bridge, adorable shops, awesome cafes and eateries, a general store, beautiful houses and side streets. All of these things combined will have you feeling like you’re the star of your very own Hallmark movie.

Best Things To Do In Woodstock, VT

Below is my list of all the best things to do in Woodstock, VT. To help you keep organized, I’ve divided some of them out by season, and also included additional things that are worth doing nearby during your visit.

1. Visit The Covered Bridges

New England is one of the best places to see the adorable little covered bridges, and Vermont is home to over 100 of them. Here in Woodstock, you’ll be able to see three! The most famous one in Woodstock is the Middle Covered Bridge, which is located right in the village.

A few minutes outside of the village, you can also see Taftsville Covered Bridge and Lincoln Covered Bridge. You’ll want to drive to these, as they’re not easily walkable from town, but they’re definitely worth venturing over to.

2. Stroll Through The Shops & Town Green

Woodstock has one of the most beautiful little downtown areas in New England, and it’s all centered around the The Green. Here, you’ll find access to Middle Covered Bridge, as well as all the shops and restaurants, and lots of beautiful side streets to wander.

While strolling around town, I suggest popping into the Vermont Flannel Company , the Yankee Bookshop , F.H. Gillinghams , and Woody’s Mercantile . When exploring Woodstock by car, I definitely suggest you make a stop at Farmhouse Pottery , too. Not only is the store beautiful, but you can watch some of the artisans at work, or even take a wheel workshop (more on that later, though).

3. Have Fun At Billings Farm & Museum

One of the most fun places to visit in Woodstock, VT is to head to Billings Farm & Museum , which is only about a mile outside of town center. During your visit to this 200-acre working dairy farm, you’ll be able to see the historic barns on the property, take in gorgeous rural landscapes, enjoy a scenic walk through their gardens and nature path, pet the animals in the barn, and even take a wagon ride around the farm.

Be sure to swing by the Farmhouse Cafe for ice cream, drinks and snacks. You can also pick up their freshly-made cheeses and butter to take home with you.

4. Explore The Marsh-Billings-Rockefeller Historical Site

The question to ask yourself while visiting the Marsh-Billings-Rockefeller Historical Site is – what can’t I do here? This is honestly such a gem, and one of the best attractions in Woodstock, VT. Here, you’ll be able to take tours of the historic mansions and grounds, hike 20 miles of nature trails, take in the beautiful gardens, go on a horseback ride, stroll through the Mount Tom Forest, and so much more.

If you enjoy serene nature walks, I highly suggest you visit. The trails through the Mount Tom Forest are really beautiful and relaxing, and some of the views along the hiking trails are truly stunning (especially in the fall!). But the best part? It’s completely free to explore on your own (there is a fee for guided tours).

5. Hike To The Top Of Mount Tom

For a bird’s eye view of town, one of the best things to do in Woodstock, VT is to hike up to the top of Mount Tom. The trailhead can be found inside the Marsh-Billings-Rockefeller Historical Site, and the hike is about 5.5 miles round trip. The elevation gain is fairly moderate, so it isn’t too challenging, but it will require a bit of a workout nonetheless.

Once you reach the top, you’ll be rewarded with really great views of Woodstock from above, and since you’re already on the trail system, you can easily connect to other hikes if you wanted to make a day of it.

6. Learn How To Handle A Falcon

If you’re interested in wildlife, one of the coolest experiences to have in Woodstock, VT is an experience with New England Falconry . This experience is the very first tour of its kind to be allowed in the U.S., and is led by a Master Falconer. You’ll learn all about these beautiful animals, as well as conservation efforts and their history. And of course, get your chance at handling one of the trained falcons.

Depending on the experience you choose, you may also get the chance to handle an owl, which is an incredibly memorable experience.

7. Taste Local Cheeses and Syrups At Sugarbush Farm

No trip to Woodstock is complete until you’ve visited Sugarbush Farms to sample some of their own cheeses and maple syrups, all of which are made right on the farm. Located only a short 15 minute drive from the main village, not only is the surrounding farmland beautiful, but you’ll get to nibble on samples of their 15 different cheeses, taste their maple syrups, and take a self-guided tour through their woods to see where the maple syrup trees are tapped.

Things To Do Near Woodstock, VT

While there are so many great things to do right in Woodstock, VT, there are also lots of opportunities to explore the nearby areas to see even more of Vermont and New England. If you’re planning a trip to Woodstock and have some extra time, I highly suggest you look into some of these options.

8. Visit The Simon Pearce Flagship Store For A Glass-Blowing Demonstration

One of the my favorite things to do near Woodstock, VT is head over to Quechee, which is only about 10-15 minutes from Woodstock. Here, you’ll find quite a few things to do, including a visit to the flagship Simon Pearce store. Famous for its hand-blown glassware pieces, all of which are made right here at this location or their shop in Maryland, your experience here will be really fun and unique.

First, the grounds are beautiful, and the shop overlooks the river and a covered bridge, and the entire store is impeccably merchandised. On site is also an amazing restaurant with views of the river and covered bridge, and it serves both lunch and dinner.

But the best thing to do during your visit is to head downstairs and watch the artisans as they craft each piece. I honestly didn’t think I would find this interesting when I first visited, but it’s now one of my favorite things I’ve done in Vermont.

9. Hike The Quechee Gorge Trail

Also in Quechee, the Quechee Gorge Trail is something you don’t want to miss for awesome views of the gorge. My favorite time of year to do this is in the fall when the foliage surrounds the gorge, but this is really a great thing to do year-round (even in winter!).

The relaxing walk around the gorge is pretty easy, and it’s just under a 1.5 mile loop that typically takes less than hour.

10. Go Antiquing At Quechee Gorge Village

We’re not done with Quechee just yet! A 5-min drive from Simon Pearce brings you to the Quechee Gorge Village, and this is definitely one of the best things to do near Woodstock, VT. This quaint little outdoor shopping village sits in the countryside and here, you can shop for antiques, browse pieces by local artisans, and sample more cheeses, wines and fudge. This is a place I always have to stop at when I visit the area.

11. Taste Locally Made Spirits

While all the shops at the Quechee Gorge Village are worth your time, one place that stands out as an especially fun experience is the Vermont Spirits Distilling Co. Complimentary tastings are offered during your visit, and they hand-craft small batches of bourbon, vodka and gin right in Quechee.

If you happen to be in the area on a Tuesday, definitely stop by for their creative cocktail bar event, held each week year-round (be sure to confirm before making a special trip, however!).

If you have a special interest in local beer and spirits, it may be worth considering this awesome tour through Woodstock. A local guide will pick you up at your hotel in Woodstock, and take you to the best distilleries and breweries in the area, and do all the driving. This leaves you free to relax and enjoy whichever samples you’d like.

Click here to book your brewery & spirits tour in Woodstock!

12. Sample The Brews At Long Trail

Continuing on with sampling some of the best drinks to come out of Vermont, Long Trail Brewing Co. is also a nice place to stop. Not only are the beers great, but their taproom has an outdoor seating area with views of the river and green mountains.

During your visit, you can get a beer flight to sample different kinds (or just go for a glass), and they also have a really tasty food menu for both lunch and dinner.

13. Take A Day Trip To Stowe

I love Stowe equally as much as Woodstock, and if you have a few days or more during your visit, I highly suggest venturing over to Stowe for the afternoon, or a full day. On a day trip here, you can visit one of my all-time favorite general stores (the Stowe Mercantile), walk a beautiful and scenic path which is especially amazing in the fall and take a gondola ride up to the highest peak in Vermont.

14. Spend An Afternoon In Hanover, NH

When you’re in Woodstock, you’re actually pretty close to the New Hampshire border, and you can easily take a quick 30-minute drive to Hanover. Home to Dartmouth College , this is another great little New England town with a really beautiful Main Street for shopping and dining, and is also home to some lovely museums. Hanover makes for a great afternoon trip, and is definitely something to consider if you want to see more of New England.

Romantic Things To Do In Woodstock, VT

Woodstock makes for the perfect place to celebrate a special occasion like an anniversary, and if you’re planning a romantic getaway, here are a few ideas to consider.

15. Do A Wheel Workshop With Wine & Cheese At Farmhouse Pottery

I’ve already mentioned Farmhouse Pottery in the shopping section of this post, but for something fun and romantic, I can’t recommend the wine and cheese wheel workshop for two enough. My husband gifted me this experience a few years back, and we absolutely loved it. Sip on some wine, nibble on some cheese, get a tour of the facility, and then get your hands in the clay to create your own piece to take home with you!

Click here for more information on Clay Dates at Farmhouse Pottery.

16. Spend The Day Getting Pampered At The Woodstock Inn’s Spa

If you’re looking for the ultimate relaxing romantic getaway, definitely consider booking a spa day at the Woodstock Inn & Resort. The spa is open to the public, so you don’t need a hotel reservation to visit, and they also have couple’s massage options for the perfect morning or afternoon together. To extend your time at the hotel, you can also book a special lunch or dinner after your massage at one of their awesome restaurants.

17. Have A Candlelit Gourmet Meal At The Lincoln Inn

One of the best dining experiences I’ve ever had was at the Lincoln Inn, and this is definitely one of the best experiences in Woodstock, VT, especially for a romantic getaway.

With a dining reservation here, your evening will begin in their cozy tavern where you can buy a glass of champagne (or any drink you’d like) to kick start your experience (which I highly recommend doing), and then you’ll be welcomed into the dining room for your 7-course tasting menu curated by a Michelin Star chef.

Forbes has even named this restaurant one of the 10 best in the country, so you don’t have to go on my word alone. But my husband and I continue to rave about our dinner here, which was also very romantic.

Best Fall Activities In Woodstock, VT

Vermont is famous for its fall foliage, and this is the time of year many people choose to visit. While everything in this post is great for a fall trip, here are some extra suggestions for fall activities that you can incorporate into your itinerary.

18. Go Apple Picking

New England is a great place to go apple picking, and if you’re looking to pick some fresh apples to take home with you, there are a few options nearby. Here are some orchards near Woodstock, VT that offer apple picking:

• Whitman Brook Orchard (Quechee)
• Wellwood Orchards (Springfield)
• VTC Orchards (Randolph)

19. Enjoy The Fall Decorations Downtown

Woodstock does such a great job celebrating holidays and bringing the community together. One of the best things to do in Woodstock, VT in the fall is to admire all the fall decorations around town. Storefronts and houses alike will be adorned with fall wreaths, pumpkins and all kinds of harvest decor to get you in the fall spirit.

20. Go On A Foliage Tree Canopy Walk

Located in Quechee, the VINS Nature Center offers the incredible opportunity to walk through the forest treetops with their Canopy Walk. While this is also open throughout the summer season as well, fall is the best time to visit because of the beautiful foliage color.

The great thing about this experience is that everyone of all ages can enjoy it, including those with mobility issues, as it’s also ADA-accessible. While walking along the platforms high in the trees, you’ll have an easier time spotting birds and other wildlife, and enjoy 360-degree views of the countryside from their treehouse.

21. Visiting Billings Farms For Their Halloween Celebrations

While Billings Farm was already mentioned, their fall celebrations definitely deserve a separate mention. This event is especially great for those with children, as they’ll be able to enjoy story time, pumpkin bowling, live music and dancing. Spiced apple cider and cider donuts will be plentiful at the Farmhouse Cafe, and there will also be cider-pressing demonstrations and all kinds of other harvest activities to take part in.

22. Get A Vermont Maple Creemee At Woodstock Scoops

While Vermont is known for its maple syrup, cheese and Ben & Jerry’s ice cream, it’s also known for its maple creemees, and getting one of these should definitely be on your list. A maple creemee is basically maple-infused soft serve ice cream, and it’s awfully delicious, especially during this time of the year. The best place to get a maple creemee in Woodstock is at Woodstock Scoops, which can be found right in the town center.

Things To Do In Woodstock, VT In The Winter

Woodstock makes for a great winter getaway destination! If you’re planning to visit during this time of year, here are my suggestions for the best winter activities in Woodstock, VT.

23. Enjoy Woodstock’s Wassail Weekend In December

To kick off the holiday season, one of the best things to do in Woodstock, VT is plan a visit during Wassail Weekend in December. The town will transform into a picture-perfect Christmas postcard and is one of the absolute best places to visit in Vermont during Christmas.

During this weekend in particular, there will be a Christmas parade, the lighting of the town yule log, caroling and special holiday events at Billings Farm.

24. Ski & Snowboard At Saskadena Six

Previously called Suicide Six until just this year in 2022, this ski area in South Pomfret is only a 5-10 minute drive from Woodstock and is the perfect destination if you’re hoping to hit the slopes on your trip. This is also one of the oldest ski areas in North America, and is continually rated as a top ski destination in New England, especially for beginners. In fact, 30% of the trails are green trails!

Rental equipment is offered on the mountain, as well as lessons for beginners or those looking to brush up on their skills.

25. Hit The Ice

Woodstock has a few options when it comes to ice skating in the winter, so if you’re looking to get out onto the ice for a winter afternoon, this is a great place to do it. Woodstock has an indoor skating rink at Union Arena, and two outdoor rinks at Vail Field right in Woodstock, and Silver Lake in nearby Barnard.

A cool feature of Vail Field is that many people have donated ice skates over the years, which are stored right at the ice rink area. The rink is free for all to visit, and for those who doesn’t have skates, you’re welcomed to borrow a pair at no charge.

26. Take A Scenic Snowshoe Walk

The Marsh-Billings-Rockefeller National Historical Site is an amazing place to strap on some snowshoes and head out into the magical winter wonderland that is Vermont during this season. The Woodstock Inn & Resort maintains over 12 miles of winter trails for visitors to use, and this makes for a really peaceful day out in nature on a chilly, winter day.

Tip : To use the trails in the winter, guests must have a valid day pass. These can be purchased at the Nordic Center. Click here for more information .

27. Go Snow Tubing In Killington

Snow tubing at Killington is one of my personal favorite things to do in Woodstock, VT in the winter. While I also love skiing and ice skating, there’s something about tubing that makes you feel like a kid again, and the tubing park at Killington is a lot of fun.

Killington is about a 30-minute drive from Woodstock, which makes it easy to visit, and they have a really convenient tubing lift system that takes you back up the hill after your adventure down the hill.

Free Things To Do In Woodstock, VT

If you’re on a budget, fear not! While Woodstock can be a more expensive destination when it comes to hotels and restaurants, there’s actually plenty to do for those looking to save a little money. Here’s a list of the free things to do in Woodstock, VT:

• Visit the covered bridges (or take a Vermont covered bridges road trip)
• Walk through downtown
• Visit Sugarbush Farms
• Glass-blowing demonstration at Simon Pearce
• Walking around Quechee Gorge
• Marsh-Billings-Rockefeller National Historical Park
• Hiking Mount Tom
• Visit Farmhouse Pottery
• Tastings at Vermont Spirits Distilling Co.
• Road trips to nearby areas like Stowe, Hanover, NH and Burlington

Best Time To Visit Woodstock, VT

Woodstock is really a great town to visit year-round because it’s so charming, but fall and winter get my vote for best seasons to visit. The fall foliage in Woodstock is truly stunning, and the winter season makes for such a cozy getaway (even if you don’t ski or enjoy snow activities).

If you plan to explore more of the state during your visit, the best time to visit Vermont in general, I think, is the fall season to admire the foliage.

Best Places To Stay In Woodstock, VT

One thing to note is that Woodstock isn’t the cheapest town to visit in New England, and accommodations are usually higher than average. I’ve listed some places below in each budget category, but keep in mind that typical “budget” accommodations don’t really exist here without going outside of town.

Luxury : For the ultimate Woodstock stay, you’ll want to check out the Woodstock Inn & Resort , which I mentioned earlier in the post. This gorgeous inn is a bit of a splurge, but if you’re celebrating a special occasion, planning a romantic weekend away, or simply want to be in the center of town, this is the perfect place to stay.

Rooms are beautifully decorated with an updated take on traditional New England designs, and there are four restaurants, a gift shop and a spa on-site for your comfort and convenience.

Click here to check out the Woodstock Inn & Resort

Moderate : 506 On The River Inn is a really great option. Located just outside of the main town area along the Ottaquechee River, you’ll still only be a 5-minute drive into town. This inn has a cozy but modern farmhouse meets traditional New England style, and rooms range from standard to farmhouse suites with kitchens. Amenities include an on-site bistro, marshmallow roasting and resort privileges at their sister property in Killington.

Click here to check out 506 On The River

Budget(ish) : The Vesper Woodstock is a cute little little B&B that’s located right in town, and has a really fun eclectic and modern style. Rooms here tend to trend a little bit less in price, but you still get some really great amenities like a complimentary breakfast included in the rate, walkability to downtown and beautiful furnishings in the rooms (some with gas fireplaces and jacuzzi tubs).

Click here to check out The Vesper Woodstock

Budget Option Just Outside of Woodstock: The Align Inn is a standard budget motel that’s a great option for those willing to stay outside of Woodstock and save a bit of money. This hotel is clean and comfortable, and for the price, it’s a great option that’s only a 15-minute drive into downtown Woodstock. Plus, don’t forget about all the fun things to do in Quechee!

Click here to check out the Align Inn in Queche

Best Restaurants In Woodstock, VT

There is no storage of amazing restaurant options in Woodstock, and here, you’ll also find a big emphasis on farm-to-table dining, making this an awesome destination for foodies. There are so many places to choose from, but below are my favorite places (excluding The Lincoln Inn, which was already mentioned above in this post!).

Mon Vert Café: Right in town you’ll find this awesome little cafe that’s a great spot for a light breakfast or lunch, or a coffee. On their menu, you’ll find things like egg dishes/sandwiches and yogurt parfaits with granola for breakfast, and salads and sandwiches for lunch (and you guessed it, a focus on local ingredients from community farmers!). They also serve alcoholic drinks!

Worthy Kitchen : A menu packed with comfort foods, craft beers and delicious desserts. Located a short drive from downtown Woodstock, Worthy Kitchen is a casual place that focuses on the farm-to-table experience, and partners with local farmers to serve only the freshest ingredients. This is a popular place, and they do take reservations through Resy.com !

Mangalitsa : Located right in downtown Woodstock, this is another casual, comfort food place in an older, renovated house. Also with a focus on farm-to-table, you’ll find homemade pastas, small plates and local craft beers on their menu.

The Prince & Pauper: Also located in downtown Woodstock, this restaurants is a community staple and very popular. The interior is very cozy and decorated in a traditional New England style, and their menu is constantly changing to offer the freshest ingredients available. If you have any dietary restrictions, reach out to them before making your reservation to ensure they can accommodate you. Reservations are required as of 2022, and it’s worth the effort for a table!

Best Breakfast In Woodstock, VT

While Mon Vert Cafe is great for breakfast, I also really enjoy Soulfully Good Café. They have awesome waffles and frittatas here, which is the perfect way to start your day in Woodstock.

How To Get To Woodstock, VT

If you’re coming from a distance, the closest International airport to Woodstock, VT is the Burlington International Airport. The closest regional airport is the Lenanon Airport in New Hampshire. From the airport, you’ll need to drive.

If you’re traveling from nearby, you’ll drive directly to Woodstock, VT.

How Far Is Woodstock, VT From Boston?

Woodstock, VT is about 2 hours and 45 minutes from Boston, and there’s lots of opportunity to stop and visit fun places along the way.

How Far Is Woodstock, VT From New York City?

Woodstock, VT is about 4.5-5 hours from NYC, depending on traffic (during rush hour, it could be longer). The best way to get to Woodstock from NYC is to drive, as public transit isn’t convenient in this area of Vermont. This is another route that offers a lot of fun places to stop during your drive.

Is Woodstock, VT Walkable?

Woodstock’s town center is very walkable, but as with most destinations in New England, you will still need a car to explore nearby areas, and to get to some of the local sites and attractions. To walk around the village center, you’ll definitely be able to park your car while there, but you’ll need it to get anywhere else.

Does Woodstock, VT Have Uber?

As of 2022, Woodstock, VT does not have Uber or any ride share services. There are also no taxi companies, so your own car is very necessary in this area.

What Is Woodstock, VT Known For?

Woodstock is known for being one of Vermont’s most picturesque and charming towns with classic New England landscapes such as covered bridges surrounded by mountains and fall foliage. Woodstock has recently become famous for being the home of Farmhouse Pottery, which has garnered attention from Oprah, and is now sold in specialty boutiques across the country.

More Of My Vermont Travel Guides:

• Vermont In The Fall
• Vermont In The Winter
• Vermont In The Spring
• All The Best Things To Do In Vermont
• Things To Do In Stowe, VT
• Best Places To Stay In Vermont In The Fall
• What Is Vermont Known For? I’ll Tell You!
• Vermont Covered Bridge Road Trip Itinerary
• Best Vermont Pumpkin Patches & Farm Stands To Visit In The Fall
• Christmas In Vermont: All The Most Festive Things To Do
• Best Things To Do In Waterbury, VT
• Awesome Corn Mazes In Vermont

You may also enjoy:

• Best New England Winter Getaways
• Best New England Christmas Towns
• Best Day Trips In New England
• The Perfect New England Fall Road Trip
• Vermont vs. New Hampshire In The Fall

That’s A Wrap On The Best Things To Do In Woodstock, VT

Now that you know all the best things to do in Woodstock, VT, you’re ready to plan your perfect New England vacation in Vermont! Whether you’re looking for a little R&R at the Woodstock Inn’s spa, or are excited about the outdoor activities like hiking and tree canopy tours, there’s a little something for everyone that makes this one of the best towns in Vermont to visit.

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26 Fun Things to Do in Woodstock VT: Vermont’s Cutest Town (2023)

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Woodstock is one of my favorite towns in Vermont. There is no place in Vermont that better captures the charm and beauty of small town New England than Woodstock.

I’ve spent lots of time in Woodstock during the 15+ years I lived in Vermont, and I’ve gotten to know it well—and really fallen in love with it! Woodstock NEEDS to be on your Vermont bucket list .

In this travel guide, I’m going to share with you 26 of the best things to do in Woodstock, Vermont, including the top attractions, hikes, places to eat, and the best activities for fall, winter, spring, and summer.

Let’s explore!

From sampling Vermont’s famous cheeses to hiking to strolling the historic Woodstock downtown, you’ll find a plethora of activities to keep you and your loved one busy on your Vermont vacation.

Table of Contents

The Best Things to Do in Woodstock VT

1. visit a working dairy farm – billings farm and museum.

Billings Farm and Museum is a beautiful property where you can stay busy for hours.

If you’re searching for things to do in Woodstock VT with kids, Billings Farm and Museum should top the list! This is a working farm that is all about demonstrations and education, and is beautiful, to boot!

Spending an afternoon here can show you a great deal about the inner workings of a Vermont farm, and you can see the animals up close and personal. 

I recommend checking their schedule before your visit. There are various programs and demonstrations throughout the day that may catch your interest, so you’ll want to plan around those.

2. Stroll America’s Sweetest Downtown

Downtown Woodstock, VT is a fabulous place for shopping, dining, and more. This cute area can get crowded on weekends or during busy events, and it’s no wonder–there’s lots to see and do.

This 1886 general store is a Woodstock staple, and is renowned as one of VT’s oldest family-run general stores. Stop here for all kinds of Vermont-made items, souvenirs, and a nice selection of wine.

Other shops in Woodstock VT to keep an eye out for: 

• Unicorn – unique gifts and novelties
• Yankee Bookshop – Vermont’s oldest running independent bookstore
• Vermont Flannel Company – stay cozy!
• 37Central Clothiers
• Red Wagon Toy Co.

Even if you’re not shopping, I recommend just taking a walk around in downtown Woodstock.You can explore the covered bridge, admire the iconic Woodstock Inn and Resort, or simply sit with coffee and people watch.

You never know who you might meet. On one of our trips to Woodstock, we got to meet this tiny polar bear named Oso.

3. Seek out the covered bridges

There are dozens of charming, historic covered bridges in Vermont , and the Woodstock area is home to several. 

Middle Covered Bridge is perhaps the most photographed, as it sits right in the center of downtown Woodstock, just off the Village Green.

Surprisingly, this covered bridge is on the newer side, having been built in the 1970’s. Despite that, it looks just as historic as the many other bridges in the area.

Head down Route 4 for a few miles and you’ll find the Taftsville Covered Bridge. This long red bridge, built in 1836, is an impressive 189 ft long. You can photograph it from a pull-off just down from the bridge. 

4. Admire Quechee Gorge

Woodstock and Quechee are neighboring towns in west-central Vermont, and a trip to one can’t really be complete without a trip to the other.

When you’re searching for things to do near Woodstock, VT, also look for things to do in Quechee, VT. There are so many, and Quechee to Woodstock is a less than 15 minute drive!

One of my very favorite sites in the region is Quechee Gorge. This awe-inspiring natural formation is best seen from the bridge on Route 4. There is a parking area just beyond the Quechee Gorge bridge, and the bridge has a sidewalk with rails, so you can safely walk out and peer into the gorge.

The gorge is especially magical in the autumn, when the trees on either side burst into remarkable hues of orange and red.

If you’re feeling adventurous, you can take a fairly short hike down alongside the gorge. The trail leaves from the parking area and takes you to some short waterfalls.

5. Eat Cheese, Cheese, and More Cheese at Sugarbush Farm & Quechee Gorge Village

No Vermont vacation is complete without cheese.

In the past, it was said that Vermont had a larger population of cows than people! Not hard to imagine, with farmland stretching for miles across the state. Either way, those cows are producing some great dairy, and Vermont’s cheesemakers are turning it into the finest cheese.

Cabot is the state’s most famous cheese purveyor, available in stores throughout the US. You can’t go wrong with a nice block of Cabot sharp cheddar. But when in Vermont, you want to try ALL THE CHEESES .

You can have a wonderful cheese feast at Quechee Gorge Village. As you walk through the village’s cute shops, you’ll find a huge spread of cheese samples, along with crackers and jams.

Give all the varieties a taste and buy a block to take home. With the abundance of cheese to sample, you may find it hard not to get greedy!

Cabot is not the only cheese in Vermont, not by a mile. A visit to Woodstock, VT demands a visit to a local farm.

Head up to Sugarbush Farm , a Vermont sugar house and 3 generation family farm tucked away in the hills, for more cheese sampling as well as maple syrup tasting.

While you’re there getting your fill of farm-made cheese, you can also walk around the 500 acre property, visit with the goats and horses, and learn about how maple syrup is made. 

6. Stroll the Village Green & Woodstock Village

Many of the shops downtown and other notable buildings comprise the Woodstock Village Historic District. This was listed on the National Register of Historic Places back in 1973. It includes 95 buildings and sites across the village center and along the Ottauquechee. 

The oval-shaped Village Green sits within Woodstock Village. On one side you’ll spot the covered bridge and on the other, the Woodstock Inn and The Norman Williams Public Library.

North of town are sites such as the Billings Farm and Museum, and parts of the f Marsh-Billings-Rockefeller National Historical Park.

A walk around Woodstock Village will make you feel as if you’ve stepped into a Normal Rockwell painting: a kind of quainter, simpler time that many of us long for.

7. Visit the Harpoon and Long Trail Breweries

Sampling Vermont beer is a must-do when traveling in Vermont.

When in Woodstock VT, make the quick 15-minute drive west to the Long Trail Brewery  to try some of Vermont’s most well-known (and well-loved) beers.

Take a brewery tour, then enjoy beer flights or snacks at their Bavarian-inspired pub. There are nice views and delicious brews–what more do you need?

You can also head to Windsor to the Harpoon Brewery.

8. Sample Local Spirits

After you’ve explored the antiques for a while, head down to the end of the shopping center and visit Vermont Spirits. There you can sample Vermont-made whisky, gin, bourbon, and more.

A free tasting lets you try four different spirits. Get ready to feel the burn a bit, but they are delicious. I especially liked the 1791 Cocktail, which had a fruity touch.

9. Learn About Glassblowing at the Simon Pearce Flagship Store

Glassblowing is a popular art in New England. There are many workshops that offer demonstrations, tours, and even lessons.

A really nice place to see glass blowing in action is the Simon Pearce Flagship Store in Quechee . This place features an elegant glassware shop, a glass-blowing studio, and a bar and restaurant.

Head downstairs first to see the glass blowing in action. Several artisans were at work during our Saturday afternoon visit. Though the room is hot and bright, these blowers seemed perfectly relaxed and happy, creating beautiful glass works with ease.

Watching them is hypnotic, but don’t be afraid to ask questions. The artisans are glad to chat with you and educate you on glass blowing.

You can step through onto the balcony to enjoy the refreshing breeze and a view of the nearby covered bridge and tumbling waterfall.

Head back upstairs and browse the wares of the shop. The shining glassware sparkles as you walk through. You will be hard pressed not to purchase some of their amazing glasses and other amazing creations.

Finally, stop for a meal, or even just a cocktail, in their on-site restaurant. The food here is divine and the atmosphere the perfect blend of relaxation and luxury. 

Trust me: get their Vermont cheese soup! Drool! If you time your meal right, you might be lucky and get one of the tables overlooking the tumbling water outside!

10. Explore a Quaint Bookshop

In Woodstock, we saw a sign for used books and had to stop. This eclectic bookstore, Pleasant Street Book Store, had lots of volumes old and new and was a fun place to browse.

They also had a nice view over the river from behind the shop.

When searching for what to do in Woodstock VT, don’t discount those hidden gems that you just might stumble across. However, if you’re keen to visit, try to call ahead as the open hours seem to vary.

11. Visit the raptors at VINS

The Vermont Institute of Natural Science (VINS) is a must-do on your Woodstock bucket list, particularly if you’re traveling with kids!

VINS is an organization dedicated to avian rehabilitation and environmental conservation. Every visit there is not only a fun, cool experience seeing birds up close, it’s a lesson in how to better care for our earth and its inhabitants.

We visited VINS with our one-year-old son recently, and while he threw passing glances at the Snowy Owls and the sharp-eyed hawk varieties, my husband and I were fascinated. 

VINS takes in birds who have been injured and nurses them back to health to be released, if possible. If that is not possible, or they are otherwise unfit for life in the wild, they may stay on at VINS as animal ambassadors. 

When you visit VINS you can see a dozen or more of these amazing raptors in their large enclosures. Throughout the day, staff gives various lectures and programs that allow you to see the raptors in action and learn about them in more detail.

It was pretty exciting when one of their hawks flew right over my head!

After hanging with your new feathered friends, you won’t want to miss the Forest Canopy Walk, which is relatively new to VINS. 

This impressive wooden walkway takes you 100 feet or more over the forest floor, near the bank of the Ottauquechee River.

While there are some parts of the Canopy Walk only accessible by stairs, such as the Eagle’s Nest and the Tree House, the majority of the path is an ADA-accessible boardwalk, and we took my son on the walk in his stroller with ease.

12. Take a Hike

There are numerous options for lovely hiking near Woodstock, VT. 

The majority of local hiking trails lie within the Marsh – Billings – Rockefeller National Historical Park. Yes, that’s right! There is a National Park in Vermont! 

This scenic property is home to miles of trails and carriage roads, offering opportunities for outdoor recreation in abundance.

Mount Tom is your #1 choice for a short yet very scenic hike. This peak will reward you with views over the town of Woodstock and the distant Green Mountains.

My friend Tara at Vermont Explored has a guide for an ideal easy to moderate hike of Mount Tom and the Pogue .

Want to get out and about for some hiking in the area? This resource for local hiking trails will tell you all you need to know.

You can also check out our article on the best Vermont hiking trails, for options near to Woodstock and farther afield. 

13. Enjoy the Ottauquechee River

The Ottaquechee River brings this region together, and it’s something not to miss. Of course, you won’t really be able to since it’s right there!

One of the best ways to make the most of Woodstock’s pretty river is by sitting and relaxing on its banks. If you stay at a hotel located on the river, you’ll have a perfect spot to do so, as my family and I did when we stayed at 506 on The River Inn last summer.

Hop into one of those appealing Adirondack chairs and watch the world go by. 

14. Catch Some Classic New England Architecture

Covered bridges? Check! Stately Vermont homes? Check! White steepled churches? Check check check!

There’s no shortage of classic New England architecture in Woodstock, Vermont.

A walk around downtown Woodstock will introduce you to much of this quintessential architecture, but don’t just stick to the main road.

Venture off into the nearby residential areas. The stately homes are beautiful, and during one of my visits to Woodstock in July, the homes were draped with red, white, and blue banners and flying many American flags.

Classic New England at its finest!

As you explore Woodstock’s Main Street area, don’t miss a look at the iconic Woodstock Inn. The lawn and flowers in front of the inn are always a treat, and this is absolutely an example of quintessential New England charm. 

15. Visit Farmhouse Pottery

This Woodstock Vermont shop is America’s largest studio pottery workshop , and in addition to their stunning selection of pottery homeware, they also offer “Clay Dates” where you can handcraft your own piece right alongside a master potter. This would be a very unique Woodstock, VT souvenir!

16. Check in With the Woodstock, VT Events Calendar

If you’re looking for things to do in Woodstock, VT this weekend or on any other specific date, be sure to check in with the Woodstock VT events calendar !

How else would you know that National Ice Cream Day is being celebrated at Billings Farm and Museum in July?

Woodstock, VT Fall Activities

17. experience woodstock vermont fall foliage.

There are many online foliage maps that you can reference to align your travel with the autumn colors, but fall in Woodstock generally is at its best in mid to late September and early October. Let’s start with something everyone wants to know: what is there to do in in the fall in Woodstock? The answer: PLENTY!

Fall in Vermont is nothing short of epic, and towns like Woodstock are absolutely ideal for leaf-peeping fun! In fact, Woodstock is on my recommended New England fall road trip itinerary .

There are so many great ways to get out and enjoy the beauty of the blazing Vermont fall foliage, whether you’re hiking, strolling downtown, or just going for a leisurely country drive!

Important Note for 2023! You may have seen in other guides for things to do in Woodstock or in countless influencer images on Instagram, a certain photogenic farm recommended. This is called Sleepy Hollow farm and in recent years has gained extreme popularity. Unfortunately, the popularity has gone too far. This farm is private property and situated on a small country road. Sadly, the inundation of tourists trying to catch a glimpse of the farm has created a number of issues, including major traffic concerns on this residential road. There has also apparently been many instances of visitors trespassing on the property and being disrespectful of this property as well as neighbors’. In 2023, residents of the area have worked together to close this road to the public during the height of fall foliage season. So, please do not attempt to visit Sleepy Hollow Farm this fall. And even when the road is reopened, I would strongly discourage you from visiting. Instead, please consider visiting one of the many public, local farms that would welcome you! These include Sugarbush Farm, Billings Farm, and others. And PS: while Sleepy Hollow is scenic, there are literally thousands of gorgeous properties in Vermont you could see with the same beautiful autumn magic. So go drive down some back roads and explore a bit. And remember, always respect private property.

18. Go apple picking

When it comes to fall in Vermont, there may be nothing more iconic than apple picking. One of the best things you can do when visiting Woodstock during this season is to head to a nearby orchard and pick-your-own apples. A few local options to consider include Whitman Brook Orchard in Quechee, and Moore’s Orchards in North Pomfret.

19. Take a fall picnic atop Mt. Peg

Get into Vermont nature with a hike on the Mount Peg Loop , a 1.3 mile trail that offers lovely views for a relatively short journey. I suggest grabbing sandwiches from Mon Vert Cafe for your picnic!

20. Take a day trip to a nearby pumpkin patch

Your fall trip to Woodstock wouldn’t be complete without another quintessential fall activity. Fortunately, Vermont is abounding in farms, so you won’t have trouble finding a festive spot to grab a pumpkin.

In Woodstock, On the Edge Farm is a great option. It’s not a traditional pumpkin patch, but an oh-so-cute farm stand in a picture-perfect setting. You can get pumpkins, flowers, pies, and more.

Woodstock, VT Winter Activities

21. experience a classic woodstock vermont christmas.

If you’re looking to experience a New England Christmas that goes all in on charm, then you need to plan to visit Woodstock VT for Christmas!

Wassail Weekend in Woodstock is the undisputed star of the Christmas season, and with good reason: carriage rides through downtown Woodstock, historic homes decorated to the nines, and music festivities all around town are just a few of the things that make a plan to visit Woodstock VT for Christmas a must for anyone looking for quaint Woodstock VT activities!

22. Hit the Slopes at Saskadena Six

Saskadena Six is one of the country’s oldest ski resorts, and it’s absolutely one of the best things to do near Woodstock VT!

Located just 5 minutes up the road in Pomfret, Saskadena Six is the place to go for outdoor adventures in summer or winter; play in the snow on the mountain while skiing or snowboarding, or embrace a Woodstock Vermont summer by participating in guided mountain bike tours, hikes, and more in this absolutely gorgeous outdoor space!

Woodstock, VT Spring Activities

23. welcome baby animals at billings farm.

A visit to Billings Farm is one of the best things to do in Woodstock, VT throughout the year. But if your visit is in the springtime, you can’t miss the Baby Farm Animal Celebration.

This event happens one day each year, and it is very special. Visitors can meet chicks and ducklings, pet baby lambs and goats, and participate in a variety of other activities including wagon rides and crafts.

This is a fantastic family-friendly event and it is a perfect way to celebrate the season of spring: welcoming new life into the Green Mountains!

24. Sift Through Endless Antiques

New England is a great place to go antiquing. I’m always surprised at the number of antique shops to be found all over Vermont and New Hampshire.

Well, if you love searching for treasures of the past, we found the trove. In Quechee Gorge Village (the same place where you can sample Cabot cheese) is an enormous antiques mall with several floors filled with antique items of all kinds.

It’s a fascinating place to walk around in. On our recent trip to Woodstock, we ran into some bad weather–exploring this antiques mall was a perfect rainy-day activity!

Woodstock, VT Summer Activities

25. attend the quechee balloon festival.

Every summer, the Quechee Balloon Festival comes to town. The longest running hot air balloon festival in New England, this is a must-attend event. You’ll have the chance to see dozens of colorful balloons in flight over the serene Vermont landscape.

You can also book for balloon rides (traditional ascension flights or tethered rides) but be aware that these book up well in advance! Next year’s Quechee Balloon Festival will be held June 14-16, 2024.

26. Learn the art of falconry

Have you ever wanted to handle a hawk? Learn how to hold an owl on your arm and then let it fly? This is something that is a total dream for me, so on my next visit to Woodstock, I am signing up for a session with New England Falconry . Your lesson in falconry with a master falconer will be an unforgettable experience. They offer a few different sessions, so you can take your pick of working with and learning about hawks, owls, and even eagles. While this is an awesome thing to do in Woodstock throughout the year, their more extensive sessions with owls and eagles are only offered April through August, so summer is prime time for this activity.

Is Woodstock, VT Worth Visiting?

Woodstock, VT is absolutely worth visiting, betweens its fall foliage, small town charm, and many things to do. If I haven’t convinced you yet, I’m doubling down to tell you YES: you should plan a trip to one of my favorite places to visit in Vermont.

When is the best time to visit Woodstock, Vermont?

The first question many Vermont visitors ask is “when should I visit Woodstock?” 

Fortunately, Woodstock is beautiful in all seasons. I’m going to share some suggestions on the best things to do in each season in a bit. Although late winter and what is sometimes called “stick season” here in Vermont is admittedly less magical.

But fall and winter are probably the standouts for most visitors, and I agree! Far and away the best time to visit Woodstock, VT is in the fall or the winter.

Woodstock has consistently been named one of the best places to visit at Christmas and one of the most beautiful towns in America. 

It consistently tops list of Vermont fall foliage locations not to be missed. People adore fall in Woodstock, with all its color and charm.

Where is Woodstock, VT?

If you’re wondering where Woodstock, Vermont is located, it’s in the east-central area of Vermont, roughly 15 miles from the western border of New Hampshire.

It’s an essential stop on a Vermont road trip , and an easy day trip from other Vermont destinations, such as Burlington , Stowe , and Manchester .

How To Get to Woodstock, VT

To get to Woodstock, you’ll need a car. The cities of Boston, MA, Albany, NY and Portland, ME are all within a drive of two to three hours. The cities of Burlington, VT and Manchester, NH are about 90 minutes away by car. All of these cities have major airports, with Boston offering the most flight options.

Places to Stay in Woodstock, VT

After a day spent adventuring around lovely Woodstock, what could be better than a wonderful spot to rest your head? There are plenty of great hotels in Woodstock, VT to choose from, and I have a couple of recommendations, depending on what you’re looking for.

The Woodstock Inn

If you’re looking for where to stay in Woodstock, VT, consider The Woodstock Inn and Resort, an exquisite property that hosts beautiful weddings; the onsite spa is considered one of the best things to do in Woodstock VT to unwind!

A stay here is definitely more of a splurge, but it is a great option for a romantic getaway in Woodstock, VT. Click here to check the latest prices and availability .

The Jackson House Inn

Another one of the hotels in Woodstock, Vermont you might choose is the Jackson House Inn. For those seeking a classic Vermont bed and breakfast experience, this is a terrific choice.

The inn is located a few miles from downtown Woodstock, providing a more country feel. Click here to check prices and availability .

The Sleep Woodstock Motel

For the budget conscious, there can be no better choice than the Sleep Woodstock Motel . In fact, this is an all-around excellent option for hotels in Woodstock Vermont! The prices are reasonable, especially since the motel feels a bit upscale.

Sleep Woodstock is a newer addition to the Woodstock area, and it is a good one as this region doesn’t have too many budget-friendly accommodation choices. Clean, cute, and homey, the Sleep Woodstock has the vibe of a 1950s motor lodge combined with the touches of a modern hotel.

My husband and I were hosted here during one of our trips to Woodstock, and we really, really loved it. The room was spacious, every feature was brand new, and the bed provided one of the most comfortable nights of sleep ever!

Our room had a fridge and microwave, too: very convenient for chilling our wine.

To top it off, the motel’s owner, Patrick, is super friendly and ready to give you tons of suggestions for things to do around Woodstock, VT, especially where to grab the best food.

We absolutely recommend Sleep Woodstock for couples, families, and other travelers. It’s an affordable motel in Woodstock, VT in a great location. Click here to check prices and availability .

Fat Sheep Farm

For a unique place to stay near Woodstock, VT, consider Fat Sheep Farm in nearby Hartland, just about a 20 minute drive from Woodstock. Fat Sheep Farm is a working farm that also offers cozy cabins for rent on this sprawling 60-acre property. For a taste of working farm life- because yes, you do get to help tend to the animals!- there’s no better opportunity than a stay at one of the coolest places to stay near Woodstock!

Check out our experience at Fat Sheep Farm here !

Where to Eat in Woodstock Vermont

There are plenty of restaurants in Woodstock, VT that beckon you to try them. Unfortunately, you’ll never get to them all in a single visit, but you can get a good sample!

When time is limited, we recommend checking out these great restaurants in Woodstock:

Eat Farm-to-Table Goodness – Cloudland Farm

You can’t miss out on farm-to-table dining in VT. The state’s immense farmland has inspired countless restaurants that use crops, meat, and more straight from the source.

One Woodstock Vermont restaurant that should be on the top of your list is Cloudland Farm. This farm-to-table operation is absolutely divine.

Cloudland Farm is found up a winding set of beautiful VT roads. The route is so woodsy that you might feel as if you’ve taken a wrong turn, but you’re on the right track. Around a final bend, you’ll see the sprawling property overlooking a stunning mountain vista.

Before your meal begins, you can sit on the veranda and simply take in the view with a glass of wine. It’s so relaxing and romantic. (Cloudland is BYOB, so plan ahead and bring along your favorite bottle of wine or a selection of beers.)

Then, it’s time for your dinner.

Get ready for an incredible meal. Each night’s menu is different, with chef-selected daily fare crafted entirely from local ingredients.

A list on your table tells you where each item has been sourced. Cloudland partners with an impressive number of farms in Vermont, New Hampshire, and even Massachusetts.

The entree at Cloudland was braised pork (raised right at Cloudland itself), herb mashed potatoes, with a rhubarb compote and a berry glaze. My husband had this, while I had a vegetarian option: risotto cakes, also with fresh rhubarb and a local egg.

Both dishes were phenomenal, served with a fresh green salad to start and finished off with strawberry crepes and basil ice cream. The entire experience was lovely, and the food flavors were brilliantly paired.

The waitstaff is great, and your dinner feels personalized and special. We highly recommend Cloudland for fine dining in Woodstock, VT.

Coffee and Breakfast in Woodstock, VT – Mon Vert Cafe

As you may know, we really love coffee! Mon Vert has excellent coffee options in a hip downtown cafe. But it’s their breakfast that keeps guests coming again and again. Wow!

We dined on fruit-topped french toast and classic biscuits and gravy. We were stuffed to the gills after our meal, but we were so, so content.

My must-order item whenever I visit Mon Vert is a maple latte. Bliss.

The staff here is amazingly friendly and down-to-earth, something that can really take a coffee shop or restaurant to the next level. 10/10 highly recommend! 🙂

Like Cloudland, Mon Vert Cafe also relies heavily on local farms and suppliers. No doubt, this is one of the reasons the food is so awesome.

More Coffee in Woodstock – Abracadabra

Another great place for coffee in Woodstock is a newer spot, Abracadabra Coffee Company. I stopped here on my most recent visit to Woodstock and it’s such a great addition to the area! As their website says, they offer “SEASONALLY SOURCED SLAMMIN’ SINGLE ORIGIN COFFEES SINCE DAY 1”. I had my usual here (a maple latte, of course) and it was terrific!

Plus, their location is fun: they’ve got a ’64 Shasta coffee trailer parked inside the shop, and the vibes are just awesome. You can find Abracadabra outside of downtown Woodstock, a few minutes up Route 12 at 35 Wayside Road. Open 6 days a week, closed Tuesdays.

Tasty Dinner in Woodstock – Worthy Kitchen

Another of the best restaurants Woodstock has to offer is found a bit east of downtown.

In an unassuming brown building, you’ll find the delicious Worthy Kitchen, a super casual eatery that is often really crowded–and with good reason. This place is deeeelish.

We ate a Saturday night meal here and had a tough time choosing what to order. Eventually, Nathan opted for a brisket sandwich, and I went classic–a cheeseburger. Both were excellent and served with good fries.

Don’t miss the nice local beer menu, either.

More Vermont travel planning here:

• 12 Fun Things To Do in Brattleboro VT
• Top 12 Fun Things to do in Killington VT

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20 Things to do in Woodstock, VT

Woodstock, Vermont is a picture-book New England Village, voted the prettiest town in America. It is the perfect place to experience the best of Vermont: architecture, spectacular natural scenery, a world heritage farm, great restaurants, eclectic boutiques and down-to-earth Vermont Hospitality.

AS TOLD BY PEOPLE WHO LIVE THERE

1. morning village walk:.

Stroll through the village green, enjoy a cappuccino at Mon Vert Cafe, wander back across the covered bridge, and see a breathtaking Vermont view from the center of the bridge.

2. EGGS & PANCAKES AT THE CREAMERY:

It is not fancy, but its delish.

3. VISIT FARMHOUSE POTTERY:

Neighbors to 506 are the beautiful and inspiring Farmhouse. Pottery guys and girls. Located in the old bible binding building. They create beautiful, functional pottery.

4. SASKADENA SIX SKI AREA & SASKADENA SIX BIKE PARK

With easy-riding terrain perfect for families and beginners, Saskadena Six Ski Area welcomes skiers and snowboarders of all abilities.

In the summers, shred our downhill tracks on mountain bikes! An expanding trail network offers flowy berms and jumps, our skills area is perfect to learn new tricks and get the little ones out on our complimentary strider bikes.

Woodstock's very own ski area. Stop by Teago General Store on the way and grab a great sandwich, hot chocolate and a taste for the local goings-on in Pomfret.

5. THE FARMERS MARKET:

Right next door to 506 is the hugely popular and world class Farmers Market. A wonderful selection of sandwiches, prepared food and baked goods are available. Don't forget to buy some of Vermont's best cheeses on display.

6. TIME TO FEED THE COWS:

Billings Farm and Museum is a heritage that we are proud to be a part of. It packages a gentleman's glimpse into farming and history in a fun Vermont setting as an experience not to be missed, especially for the kids. Wagon rides are on offer throughout the year. Check for schedules.

7. MARKET ON THE GREEN:

Every Wednesday, visit the Village Green for a selection of fresh produce, prepared food, crafts and live music.

8. SUGARBUSH FARM:

A living, thriving Vermont Farm as it should be. Sample cheeses, learn how maple syrup is made and enjoy experiencing our agricultural heritage in action.

9. CALVIN COOLIDGE HOMESTEAD DISTRICT:

Vermont is the birthplace and boyhood home of Calvin Coolidge, the 30th President of the United States.

10. GILLINGHAM'S:

Woodstock's oldest store - operating since 1858. Step back in time to an authentic general store with a modern twist and a great variety of Vermont products, crafts and gifts.

11. HISTORIC PARK:

Enjoy the architecture and grounds of this beautifully preserved mansion.

12. THE VILLAGE BUTCHER:

Grab a sandwich from the Village Butcher. Then enjoy it at the Historical Society. The extensive back lawn is open to the public and offers beautiful views of the Ottauquechee River.

13. SIMON PEARCE: A TRUE VERMONT EXPERIENCE 15 MINUTES FROM 506.

Glass blowing, a world class retail experience and a delicious restaurant overlooking the stunning Quechee covered bridge and waterfall await you in this haven of creativity.

14. LONG TRAIL: FOLLOW THE TRAIL TO THE RENOWNED LONG TRAIL BREWERY.

Sample the range of brews from one of the most the beloved brewers in Vermont and dine in the casual, rowdy restaurant on the banks of the Ottaquechee Rive

15. CLOUDLAND FARM:

A wonderful farm-raised dinner awaits in a magical setting. Advance bookings required

16. MT. TOM : 30-45 MINUTE HIKE TO THE TOP.

Bring packed lunch and enjoy beautiful views of Woodstock Village.

17. THE WOODSTOCK HISTORICAL SOCIETY:

A must for any yesteryear fan with a unique insight into the history of Woodstock and the area.

Stories and photos of the creation of Woodstock are on display, as are the recollections of famous and not-so-famous people who lived and visited this special town over years gone by.

18. TOWN SUPPER:

Organised by the community in various granges and town halls across the state.

They are a wonderful experience of community and delicious home cooked food, in a charming and unique setting.

19. BARNARD LAKE SWIM AND LUNCH AT THE BARNARD STORE.

This is splendid with a great full day bike ride on the Stage Road back.

20. WOODSTOCK COUNTRY CLUB:

Round of golf or a winter cross country ski at the Robert Trent Jones designed Woodstock Country Club

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15 Top-Rated Things to Do in Woodstock, VT

Written by Barbara Radcliffe Rogers Updated Mar 24, 2023 We may earn a commission from affiliate links ( )

Barbara Radcliffe Rogers and her husband, photographer Stillman Rogers, live over the border in neighboring New Hampshire and are frequent visitors to Woodstock. They especially enjoy the town's lively art scene.

From its early years as a shire town, the regional center of courts, Woodstock attracted professionals and people of means. Later it would continue to bring professionals, merchants, and wealthy families, whose fine homes line The Green, Elm Street, and Pleasant Street.

The legacy of wealthy benefactors has been shaping the face of Woodstock for very close to two centuries. Two of the principal attractions for tourists are part of this legacy, a well-preserved "gentleman's farm" and the lovely mansion and gardens of the Marsh-Billings-Rockefeller National Historic Park.

There are plenty more things to do in Woodstock's picture-perfect downtown, from gallery hopping and shopping to strolling along its streets and admiring the historic homes and their gardens.

Nearby places to visit include Quechee Gorge and a hilltop maple farm, while active travelers can enjoy the trails on Mt. Tom year-round. You'll have no trouble finding things to do in Woodstock, Vermont.

1. Visit Billings Farm & Museum and the Sunflower House

2. marsh-billings-rockefeller national historic park, 3. explore quechee gorge, 4. photograph covered bridges, 5. take a hike on mt. tom, 6. learn about maple syrup at sugarbush farm, 7. browse in gillingham store and downtown shops, 8. visit the woodstock history center and garden, 9. st. james church and the green, 10. meet raptors at the vermont institute of natural science (vins), 11. go cross-country skiing, 12. go gallery hopping and smile at the town smiler, 13. go antique shopping, 14. ski at saskadena six, 15. take a sleigh or carriage ride, woodstock, vt - climate chart.

The farm where environmental agriculture pioneer Frederick Billings raised his Jersey cattle is still a working farm, open to visitors as Billings Farm & Museum. Along with the barns, sheds, and shops of an active farm are exhibit areas that illustrate early farming and rural life in Vermont.

You can tour the home of the farm's manager and the creamery downstairs with all the equipment used to make butter and cheese; butter-making is often demonstrated here. Throughout the year, special events highlight seasonal activities on the farm, with hands-on experiences designed for children.

The most recent attraction at the Billings Farm & Museum is the 20,000-square-foot Sunflower House , where thousands of sunflowers are planted in a maze-like pattern of rooms and corridors. The "rooms" are planted in 100 different varieties of sunflowers, some with blossoms more than two feet in diameter and growing as high as 14 feet. This garden opens at the beginning of August and blooms through early September, with its prime in mid-August.

Other special gardens to visit include a Victory Garden; a garden of heirloom varieties; and a Pollinator Garden, dedicated to plants that attract and support bees, butterflies, and beneficial insects. Kids love the Pizza Garden, where the vegetables and herbs for favorite toppings grow.

Address: 69 Old River Road, Woodstock, Vermont

Official site: https://billingsfarm.org/

Adjacent to the Billings Farm & Museum and incorporating hillside land that was also part of Frederick Billings' vast estate, the home of Billings and later the Rockefellers is Vermont's only National Park . Before Billings owned the mansion, it was the home (and birthplace) of the early pioneering environmentalist, George Perkins Marsh.

Throughout its history, the land behind the mansion has been owned by people who valued forestry and land management, and the park continues to be dedicated to demonstrating sound and forward-looking land stewardship. Ranger tours explore what is one of the oldest scientifically-managed forests in the country.

The Queen-Anne-style mansion is decorated to high Victorian tastes, featuring Tiffany glass windows and embossed wallpapers, detailed woodwork, and fine furnishings. Throughout is the Rockefellers' collection of early American landscapes, especially those of the Hudson River School artists.

The formal gardens , which are free to visit, were designed by several of America's foremost landscape architects.

Address: River Road, Woodstock, Vermont

Official site: http://www.nps.gov/mabi/index.htm

Five miles from downtown Woodstock, Quechee Gorge is one of Vermont's top tourist attractions . You can view it from the bridge that carries Route 4 165 feet above the fast-flowing Ottauquechee River, or you can hike down to walk along the river level at the bottom of the gorge.

Like much of Vermont's landscape, the gorge was formed as the glaciers receded, about 13,000 years ago, and has since then been carved deeper by the river. The trails and gorge are part of Quechee State Park , where there are both cabins and campsites. Ranger programs include guides hikes, nature games and crafts, and campfire programs.

Address: 5800 Woodstock Road (Route 4), Quechee, Vermont

In Woodstock, you can add four covered bridges to your photo album, one of them right in the town center within sight of the Green. Called Middle Covered Bridge , it's a lot newer than it would appear, constructed in 1969 using traditional methods and materials, including wooden pegs instead of nails.

Not far west of the center, Lincoln Covered Bridge crosses the Ottauquechee River close to Route 4, in West Woodstock. Built in 1877, the one-lane bridge is on the National Register of Historic Places .

Visible from Route 4 on the other side of town, the red Taftsville Covered Bridge is one of the oldest in the country, built in 1836, and spans 189 feet.

A little farther east on Route 4, a left turn into the village of Quechee takes you down Main Street and across the Quechee Covered Bridge. It was rebuilt in 2012 after it was severely damaged by the rushing floodwaters of the Ottauquechee River in the wake of Hurricane Irene. From the walkway, you can get views of the waterfall at the old mill dam.

Mt. Tom rises steeply from the banks of the Ottauquechee River and is crisscrossed by a network of about 20 miles of trails and old carriage roads.

The four-mile climb to Mt. Tom's South Peak , where there are sweeping views of the town and mountains to the west, is a gentle one, through a mixed forest.

You can combine a climb to South Peak with The Pogue , a 14-acre mountain pond, in a four-mile loop trail , also moderate. For more of a workout, follow the two-mile Precipice Trail .

In the winter, most of this trail network is groomed for cross-country skiing .

The trails are a short walk from the center of town, or you can park at the Billings Farm. Many of the trails are in the national park lands, and you can download a geo-enabled map from that website.

You can watch two rural Vermont traditions in practice at Sugarbush Farm, high in the hills above Woodstock. Maple syrup and cheddar cheese are both produced at the 500-acre farm, which has been in the Luce family for three generations.

In late winter and early spring, the farm is humming with activity as sap is brought in from the maple forest to be boiled into syrup; you can watch the operation then, and at other times of year, follow a trail through the woods to learn more about the process from tree to table.

When cheese is being made, you can watch through windows in the dairy, and at any time you can sample 15 cheese varieties and four grades of maple syrup .

The shop is a lively emporium of Vermont-made and Vermont-centric goods, with shelves of locally produced condiments and every maple product you can imagine, from lollipops to mustard.

Note that roads up the hill are unpaved, so call first before venturing to the farm in the winter or in the early spring "mud season."

Address: 591 Sugarbush Farm Road, Woodstock, Vermont

Official site: https://sugarbushfarm.com/

Central Street (Route 4) and Elm Street form the shopping district of the tidy downtown, each lined with substantial 19 th -century brick mercantile buildings.

The small specialty shops are independently owned, featuring largely high-end merchandise and Vermont-made products. The Vermont Flannel Co . specializes in quality winter clothing and sportswear. Take home a piece of Vermont with a flannel shirt, pajamas, or loungewear in traditional woodsman's red-and-black check.

Gillingham's , on Elm St., is the only store carrying a variety of merchandise, and you'll want to stop there. Gillingham's is an updated version of a traditional Vermont country store, without any pretenses. There's no cute old woodstove with a rocking chair and no penny-candy counter, but if you peruse its far corners, you'll find old-fashioned cookware for serious cooks, tools, sporting goods, and warm wool mittens. You'll also find a good variety of Vermont-made condiments and a section of quality art supplies.

You'll want to stop at the Yankee Bookshop on Central Street for its selection of Vermont authors, along with current best sellers, mysteries, and books on local subjects, as well as "bookish gifts."

The 1807 Dana House was home to three generations of the same family until 1942, when it became a museum. The owners had a dry goods store in the brick building next door, and their house is furnished in period antiques.

Textile arts and early American toys are strong points in their collections; use the flashlight beside the fully furnished dollhouse to appreciate the details and craftsmanship. Exhibitions change regularly to spotlight different collections, such as the exceptional group of fans dating from 1770 to 1930. Another one highlighted the lives of Woodstock men and women who served in World War II.

Around the house and extending over the lawns to the river are beautiful gardens with beds of heirloom perennials, sculptures, and benches.

Even if the museum is not open when you visit, stop to see the gardens and read the interesting historical signs along the walkway.

Address: 26 Elm Street, Woodstock, Vermont

Official site: www.woodstockhistorycenter.org

The stone English Gothic church of St. James makes an eye-catching exclamation point at the far end of Woodstock's long public green. Built in 1907 of stones from nearby Quechee, it was designed by Ralph Adams Cram, designer of the Cathedral of St. John the Divine in New York City, and is considered one of his best small churches.

The bell in its tower was made in the foundry of Paul Revere and is one of six Revere bells in Woodstock (this is the only town with so many, which indicates its prosperity even in the early days). Four are in use today: at St. James, the Masonic Temple on Pleasant St., the First Congregational Church on Elm St., and the North Universalist Chapel on Church St.

The Woodstock Inn & Resort , which also overlooks The Green, has two Revere bells: one on the lawn and one at the Woodstock Country Club.

A walk around The Green will reveal several historic buildings, including the brick Ebenezer Fitch House and the elegant 1883 Norman Williams Public Library . Avid readers should stop to peruse the continuing book sale in the library foyer.

Address: 2 St. James Place, Woodstock Vermont

Not far from Quechee Gorge, the Vermont Institute of Natural Sciences is a nature center whose purpose is to return injured raptors to the wild and to educate visitors about the critical role of raptors in the natural environment.

You can meet these birds close up in the center's Avian Ambassadors presentations, which feature a rotating cast that includes a peregrine falcon, a red-tailed hawk, a barred owl, barn owl, kestrels, and six species of hawks.

Elsewhere at the center, you can walk through a 2,160-square-foot naturally landscaped songbird aviary, see an exhibit about forests, and learn about reptiles.

The creative nature playground and the "Birds are Dinosaurs" exhibit showing the evolution through skeletons, life-sized replicas, and hands-on activities are favorites for kids, making this one of Woodstock's most popular things to do for families .

The innovative Forest Canopy Walk was designed so people of all abilities can enjoy looking over the forest from a 50-foot-high platform. This is achieved by building a relatively level ADA-accessible boardwalk where the land slopes to the river, so that its highest point is at eye-to-eye level with birds in the treetops. The Eagle's Nest and Tree House are elevated viewing points reached by stairs.

Address: 149 Nature's Way, Quechee, Vermont

Official site: https://vinsweb.org

Woodstock is one of the best places in Vermont to ski cross-country , with 10 kilometers of level trails in the village, 20 more on the slopes of Mt. Peg, all part of the Woodstock Nordic Center at the Woodstock Country Club.

The carriage roads and trails on Mt. Tom , at the other side of the village, provide nearly 30 kilometers more skiing, over varied terrain through the Marsh-Billings-Rockefeller National Historical Park.

You'll find more than 45 kilometers of trails groomed for skate and classic skiing, and plenty more ungroomed for backcountry skiing and snowshoeing. You can rent equipment and take lessons or guided ski and snowshoe tours at the center, where you can access the Mt. Peg trail network.

Address: Woodstock Country Club, 76 South Street, Woodstock, Vermont

Official site: www.woodstockinn.com

Perhaps because of the beauty of the village and its natural surroundings, Woodstock has drawn artists, who in turn find an appreciative market for their work. So it's not surprising that the town should be a hub for art galleries and fine crafts.

One of Vermont's most beautiful galleries is in a stone former mill building beside a brook on Central Street. Collective the Art of Craft is a co-op of fine artists and craftspeople working in various media. The shop is a showcase of brilliant blown-glass art, delicate watercolors, handwoven woolens, wood sculpture, metal arts, silver jewelry, and more one-of-a-kind works of art.

The Woodstock Gallery and Focus, A Vermont Gallery are side-by-side at the corner of Elm and Central Streets; Polonaise Art Gallery is opposite on Central Street; and farther west, on Pleasant Street, is Chip Evans Paintings . A few steps off Pleasant, on Lincoln Street is Clay Kanzler Studio . On Route 4 near the Woodstock Farmers Market, you'll find traditional pottery at Farmhouse Pottery.

Stop in front of the galleries at the corner of Elm and Central Streets to see the latest work of Artist Adrian Tans: a large chalkboard that was once a bulletin board called The Town Crier. When the pandemic ended community events for a time and there was nothing to post, Adrian Tans began bringing smiles to passersby with his large, colored chalk paintings.

The sign above was changed to "The Town Smiler," and his colorful paintings are now a well-established part of Woodstock life. They change about every two weeks and may relate to seasonal events or holidays or may just be artistic commentary of Vermont life. They will always make you smile.

In a town so filled with distinguished 19 th -century homes, a taste for antiques is not surprising. Woodstock and Quechee will keep any avid antiques shopper busy.

Begin at Wigren Barlow Art & Antiques , on Pleasant Street, to find fine antiques and vintage treasures displayed artfully in bright, uncrowded room settings. Along with 19 th - and 20 th -century paintings, the shop represents several contemporary artists, highlighting the relationship between art and antiques.

Nearby, Eric Nesbitt Art & Antiques showcases folk arts along with period furniture, tableware and art. While in the neighborhood, look for first editions and rare books across the street at Pleasant St Bookstore.

For vintage clothing and linens, stop at the tiny Who Is Sylvia in the center of town.

Two large antiques centers are in Quechee:

Near the gorge on Route 2 is the Vermont Antique Mall , a group shop of 17,000 square feet of space filled to the brim with furniture, China, antique tools and kitchenware, and other collectibles.

You could get lost just as easily in the warren of rooms at the nearby Antiques Collaborative on Route 4, where you'll find everything from magnificent Chippendale chests and Windsor chairs to African masks.

Woodstock holds a position in Vermont's long history of downhill skiing; in 1934, a group of skiers rigged a rope tow on a hillside at Clinton Gilbert's farm, powered by an old Model T engine. Purists scoffed that the sport was ruined, but the idea caught on; it was the first rope tow in America, and it marked the beginning of the ski industry.

While it's far from the biggest of Vermont's ski resorts , the 24 trails and slopes of Saskedena Six (formerly named Suicide Six) offer gentle runs for beginners and challenges for intermediate and expert skiers. Its short lift lines and laid-back atmosphere make it a favorite place to visit for families who like to ski.

Address: 247 Stage Road, South Pomfret, Vermont

Official site: https://www.saskadenasix.com/

Kedron Valley Stables offer two of the most romantic things to do for couples in Woodstock. Sleigh rides glide across fields and through woods, with views of the rolling snow-covered landscapes of South Woodstock. Carriage and wagonette rides follow the country roads in South Woodstock, one of Vermont's most beautiful village ensembles.

A white church, Grange Hall, country store and a cluster of stately brick and wood homes clustered around the brick stagecoach tavern make up the South Woodstock Village Historic District .

Address: 4342 South Road, South Woodstock, Vermont

Official site: https://www.kedron.com

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Things to Do in Woodstock

10 Top Things to Do in Woodstock, Vermont

Ken Wiedemann / Getty Images

If you are interested in seeing historic covered bridges, picture-perfect farms, a national park, an approachable ski mountain with slopes for all abilities, and art galleries, then Woodstock, Vermont,  should be your next vacation destination.

While Woodstock's population barely tops 3,000, this particular area on the eastern side of the state has every element you'd expect if you're dreaming of a quintessentially Vermont getaway.

Celebrate All Things Calvin Coolidge

James P. Blair / Getty Images

Just a 20-minute drive from Woodstock in Plymouth, you'll find two sites dedicated to the 30th President of the United States, Calvin Coolidge. Learn about his early days and presidency at the President Calvin Coolidge Historic Site , which was his birthplace and childhood home; today, it looks and feels much like it did back when he lived here in the late-1800s through the early 1930s.

Nearby, you'll find his gravesite, as well as Coolidge State Park , which makes a wonderful place for an afternoon hike or picnic. Those who wish to spend a night camping under the stars in tents or RVs can do so here—they'll also get complimentary access to Echo Lake as part of a partnership with Camp Plymouth State Park , 10 minutes away and a beautiful place to go swimming in summer.

Hike to the Top of Mount Tom

Danita Delimont/Getty Images 

At 1,250 feet, Mount Tom is hard to miss. Luckily for anyone wanting to view the village of Woodstock from above, its easy to reach, taking most hikers only about 30 minutes via a trail that begins behind the covered bridge on Mountain Avenue. If hiking isn't your forte, you can also drive along Route 4, turn right after the Farmer's Market, and keep your eyes peeled for the parking lot.

While you'll be treated to beautiful views of the town below all year long, it's especially memorable to snowshoe up the trail in winter. From the top of Mount Tom, you'll have the option to continue along other trails like the 4.2-mile Pogue and Mount Tom Trail , which leads you on a loop past a lake, or the Faulkner Trail , which takes you on a 4.2-mile journey by the river (both are considered to be moderate hikes).

Visit New England's Most Photographed Farm

Loop Images / John Greim / Getty Images

About 15 minutes south of Woodstock off Route 106 in Reading, you'll find a scene that may seem instantly familiar. A family owned business for more than 50 years, Jenne Road Farm is widely believed to be New England's and perhaps even the nation's most photographed farm.

A shot of this photogenic landscape, especially in autumn, is one that amateur, professional, and even Hollywood photographers and filmmakers have been drawn to for years. And what they're coming to capture is the picture-perfect and iconic rural scenery: the old red barn and outbuildings, rolling hills, trees that turn brilliant colors in the fall, and the reflecting pond.

Experience Rural Vermont Heritage

Billings Farm & Museum

Visit Billings Farm & Museum to learn about the evolution of agricultural practices in Vermont and see what goes on behind the scenes of a working commercial dairy operation. It's also a fun place for kids to experience farm life in an interactive, hands-on way.

The farm, which Frederick Billings founded in 1871, has been a public attraction since 1983. With a resident herd of more than 70 fine Jersey cows, this still-working farm offers daily programs, seasonal events, and educational exhibits that allow kids to observe and appreciate farm animals like horses, chickens, and sheep, and to try chores like churning butter.

Ski Suicide Six

Woodstock Inn & Resort 

In South Pomfret, The Woodstock Inn & Resort's Suicide Six ski hill, known as the earliest ski resort, has a storied past. In 1934, an improvised rope tow powered by a Ford Model T engine was installed on a hill at Gilbert's farm. The operation was later moved to a nearby hill they called "Hill 6" and a university ski coach was quoted as saying "to ski down Hill 6 was suicide," thus the name, which still exists today.

Suicide Six may have only 24 trails, but there is terrain suitable for all abilities from beginner to expert level. The ski area is open to the public and accessible via a free shuttle from the Woodstock Inn & Resort; check with the inn for lodging / ski packages and prices.

Watch, Shop, and Dine at Simon Pearce

Simon Pearce Restaurant

It's been more than three decades since Irish designer Simon Pearce crossed the pond and set up his workshop in an old textile mill down the road from Woodstock in the village of Quechee. The mill remains a must-visit attraction, where you can observe glassblowers and other artisans at work producing Pearce's distinctive pieces.

Make reservations to enjoy lunch, dinner, or Sunday brunch at the acclaimed romantic restaurant on-site, which serves fare prepared with local ingredients on exquisite Simon Pearce china with views overlooking a covered bridge and the Ottauquechee River waterfall.

Visit Vermont's Only National Park

Kim Grant / Getty Images 

Laurance and Mary Rockefeller gave Vermont an incomparable gift: their home in Woodstock. Marsh-Billings-Rockefeller National Historical Park was established in 1992, opened to the public in 1998, and is a fascinating place to visit if you love art, history, environmentalism, or the natural beauty of the outdoors.

George Perkins Marsh, one of the first people in the United States to articulate ideas about conservation, grew up on this property, and his philosophies were embraced and put into practice by equally passionate land conservation advocate Frederick Billings, who bought the Marsh estate in 1869. The Rockefellers, the final owners of these 550 acres, insisted the house where they summered be kept just as they left it, complete with their remarkable art collection.

Reserve a guided tour of the Mansion and gardens in advance; the sites are open from Memorial Day weekend through the end of October.

Sample Cheese and Maple Syrup

Sugarbush Farm Maple & Cheese Farm 

Sugarbush Farm , just a 12-minute drive from Woodstock, has 500 lovely acres and is a great place to order a special gift, Vermont-made cheese. Stop by this Woodstock farm while you're in town for free samples of more than a dozen cheeses and four grades of Vermont maple syrup , plus mustards, jams, and other items. Shop all you like for tasty Woodstock souvenirs and watch a video on how the syrup is made.

Sugarbush Farm is open to visitors every day except Thanksgiving and Christmas, and admission is free. In March and April, you can see the syrup-making process in action. You can also venture down a nature trail to the maple sugar woods. 

See Charming Covered Bridges

TripSavvy / Makito Umekita

Woodstock claims three of Vermont's more than 100 covered bridges ; a visit is a nice way to soak up some charm and to get a sense of the town's past.

Middle Covered Bridge, which you'll find on Mountain Avenue across the Village Green from the Woodstock Inn & Resort, is actually a fairly modern structure built in 1969 in authentic covered bridge style.

Head three miles west of the Village Green on Route 4 to view historic Lincoln Bridge, which dates to 1877 and is the country's sole Pratt-type truss bridge constructed of wood. It is listed on the National Register of Historic Places.

Taftsville Bridge sits four miles east of the Village Green on Route 4. Vermont's third oldest covered bridge, which was originally built in 1836, it had to be extensively restored following 2011's Tropical Storm Irene.

Enjoy a Farm to Table Meal

Courtesy of Cloudland Farm 

Experience true farm-to-table dining at Cloudland Farm in Pomfret. The restaurant is located on the Emmons family farm, where much of the meat, produce and herbs are sourced. Farm-to-table dinners are served on Thursdays, Fridays, and Saturdays by reservation.

While you are there, check out the farm, take photos of the animals and scenery and, before you leave, shop at their farmers' market for local meat, produce, and pottery.

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15 Best Things To Do In Woodstock, Vermont

by Mark and Kristen Morgan

Published: August 9, 2021

UPDATED: May 22, 2024

The tiny town of Woodstock in central Vermont epitomizes a captivating and quintessential New England village, filled with attractive historic buildings and a relaxing aura. So what should you do when you visit such a tranquil place? Well, we’re going to show you the 15 best things to do in Woodstock, Vermont to get your travel itinerary filled up to the brim.

Woodstock may be tiny in size but it is enormous in popularity and it is one of the most visited places in all of New England during Fall . Visiting Woodstock falls into the category of ‘a calming and peaceful escape’, which might come as a relief if you are driving a longer and more action packed New England road trip.

There are a a handful of must-visit attractions in Woodstock but there is no need to rush around. Woodstock is one of the most beautiful places to visit in Vermont . It is a place you take things slowly, enjoy the finer things in life and appreciate the sound of birds chirping or colorful leaves rustling in the wind.

Descriptive words like quaint, charming and picturesque can be overused at times. However, in this instance, the extraordinarily idyllic town of Woodstock in central Vermont is all of those adjectives, with a splash of enchantment and a dash of irresistible appeal thrown in for good measure.

Let’s take a look at 15 of the best things to do in Woodstock, Vermont!

Top Tips For Visiting Woodstock In Vermont

Before we jump into the best things to do in Woodstock VT, let’s take a brief look at some our top tips for you to consider when planning your trip:

• Woodstock is an incredibly popular touristy stop off in Vermont.
• We highly recommend including a stop in Woodstock on any USA road trips including Vermont.
• It’s hard to put into words how beautiful Woodstock is in the Fall season.
• Hotels are not cheap, so we recommend you book ahead to find value.
• If Woodstock is too expensive, consider staying somewhere nearby instead.
• Depending on your travel style, you could spend 1 hour or 1 day in Woodstock, VT.
• The town is very small but there are plenty of places to park.
• Take time to simply walk around the town and green spaces.
• But also jump in the car and drive around the maze-like narrow country roads.
• Bring spare batteries for your camera, you’re going to need them!

We enjoyed our visit to Woodstock in Fall so much that we were left with no choice but to include it in our popular guide to the 50 best places to visit in the USA .

Best Things To Do In Woodstock, Vermont

1. Admire Jenne Road Farm

The town of Woodstock is lovely to walk around, but the best way to really see this stunning part of Vermont is to explore the country roads and find magazine front cover scenes such as the one at Jenne Road Farm.

Magazine front cover is not an exaggeration. Jenne Road Farm is regarded as one of the most photographed barns in the world.

It has appeared on television adverts, every single New England fall foliage calendar and it was even used in a scene from timeless classic movie Forrest Gump.

What we love most about this experience is how understated it is. The only sign you will find is a tiny board stating ‘maple syrup’ with an arrow. There are no bells and whistles, despite its obvious fame.

We were shocked to be the only car on the dirt road when we visited in October, which is when it is most popular. It goes without saying, but keep your distance and don’t get too close to the private barn.

Photographers will typically stand in a line next to a tree close to where we took our photo above. There’s even a sign showing photographers where to stand to get this iconic New England picture.

To reach Jenne Farm, head South from Woodstock on VT-106 until you reach Jenne Road. It’s just over 8 miles and should take no longer than 15 minutes.

This is one of those truly unmissable things to do in Woodstock for serious photographers.

2. Taste Local Cheese & Syrup At Sugarbush Farm

Sugarbush Farm is a completely different experience. You won’t need your camera for this one but you will need your taste buds ready to sample 15 kinds of cheese and 4 grades of maple syrup produced on site.

Not only can you can taste delicious cheeses and syrup but you can also walk around a maple syrup self guided tour with information about tapping sap lines and boiling houses. Plus, farm animals roam the grounds in Summer, perfect for the younger kids.

The farm is open every day from 9am – 5pm and the entire visitation is free of charge. However, your wallet will be in danger once you’ve tried the cheese and syrup, you can trust us on that one!

Find more information at the Sugarbush Farm website .

3. Photograph Stunning Sleepy Hollow Farm

Finishing off our favorite farms in the area with another of those insanely photogenic Vermont postcard scenes. We have to be honest, we’re not sure why this one at Sleepy Hollow Farm isn’t quite as famous as Jenne Road?!

Remember we said we were the only car at Jenne Road? The same can’t be said here. We were two among maybe 15-18 other photographers at a frustratingly dull sunrise.

We decided to come back later in the morning once the grey blanket had burnt off and fortunately the beautiful fall colors were illuminating upon our return.

If we could choose just one place to photograph again in New England during Fall it would be Sleepy Hollow Farm. It looks gorgeous in photos but it looks even better in person.

Please remember this is a private farm and you can’t go down the road at all. There is a sign but some people choose selective reading ability at times!

Photographers – Don’t forget your tripod if you visit for sunrise, you’ll need it for low light to keep your ISO down.

Sleepy Hollow Farm is under 3 miles from Woodstock. Heading north on Old River Road, turn left onto Cloudland Road and follow it until you reach the farm. There are no parking spaces and it is on a very narrow road, so you’ll have to get your vehicle tucked right in against the side.

Need help planning your New England road trip?

Our popular New England fall travel guidebook helps you with planning every aspect of your road trip, including the best places to stop, where to see fall colors, where to eat and stay, itinerary ideas and map!

4. Don’t Miss Nearby Taftsville Covered Bridge

Vermont is home to more covered bridges per square mile than any other US state and Woodstock is one of the best places to set up base for a bridge hunt.

Taftsville covered bridge was built in 1836 and is the oldest standing example of a historic covered bridge in Vermont, which makes it a dead-cert on your Woodstock itinerary. It is 189 ft long and has an attractive classic red colored exterior.

A small dam and waterfall along the Ottauquechee River are located just to the northwest side of Taftsville covered bridge as you look at a map.

You can park up on Old River Road and walk down a riverside path to open up incredibly photogenic views looking back at the bridge and waterfall.

The only issue is with electrical pylons and lines, which do go some way to ruining the picture – but people need power, right?! Hopefully in future those lines can be moved underground.

5. Walk Across Woodstock Middle Covered Bridge

Taftsville is important because it’s the oldest in Vermont, but you don’t even need to leave Woodstock to see your first example of a stunning covered bridge.

In fact, the gorgeous dark wooden colored Woodstock Middle covered bridge is smack-dab in the center of Woodstock, right on the edge of ‘The Green’.

If you look on google maps, the bridge appears on Elm Street, but that isn’t correct. Woodstock Middle covered bridge is on Mountain Ave, crossing the Ottauquechee River.

There are ample places you can park alongside The Green if you’re not staying in Woodstock or are just driving through. Don’t miss the chance to walk through the bridge to grain an appreciation for expert craftsmanship and intricate details in the design.

Personally, we thought Woodstock Middle covered bridge was one of the most visually appealing of all the bridges we saw in Vermont. Not all bridges have pedestrian access, which makes this particular bridge in town one of the things you can’t miss when in Woodstock, VT.

6. See Jersey Dairy Cows At Billings Farm & Museum

One of the most popular things to do in Woodstock is to walk around the Billings dairy farm and learn about farming in Vermont from the late 1800’s to the present day.

Billings farm was established way back in 1871 and is best known for its Jersey dairy cow breeding. However, this is more than just a farm.

Not only can the kids pet farm animals and explore a working farm, there is also a huge emphasis on farming education. Exhibits and display showcase what life was, and is, like as a farmer in Vermont.

You can walk around the old farm manager’s house built in 1890, stroll along a riverside path or through gardens when in season, soak up gorgeous views over acres of land and self guide your way through farm life exhibits.

There are two dedicated parking lots for Billings farm and you do not need advanced reservations. You can either drive or walk to the farm from downtown Woodstock, which is just half a mile away.

Entrance prices are US$ 16 / adult, US$ 8 / ages 4-15 and Free for under 4’s.

Opening hours vary depending on season, check times here .

7. Explore Quechee Gorge and Village

Quechee is a popular stop along the typical Vermont or New England road trip, but many only visit the Quechee Gorge bridge before moving on to Woodstock.

We highly recommend you set aside a little more time, firstly to walk along the easy gorge-side trail but mostly to visit the village of Quechee itself afterwards.

Views over Quechee gorge are best from the bridge, but the gorge-side walk is still picturesque and worth 15 or 20 minutes to blow off the cobwebs.

Once done with the gorge, continue towards Woodstock but turn right on Waterman Hill Road and descend until just before Quechee covered bridge.

Park up and walk through the pedestrian walkway on Quechee covered bridge. To the right you will see a collection of boulders in the Ottauquechee River, but the view to the left is the reason for including Quechee village on your trip to Woodstock.

The waterfall and dam with perfectly reflective water surface above create a stunning scene, no matter the season you visit.

See the overhanging veranda and red brick building in the photo above? That is the award winning and very highly regarded restaurant the Mill at Simon Pearce, along with a glassblowing studio, which is open to the public.

See information about glassblowing viewing hours and the Mill to book reservations .

8. Enjoy The Stunning Woodstock, VT Architecture

Perhaps surprisingly for this region in Vermont and New England, Woodstock is not quite as colonial as you might imagine.

In fact, you will find a wonderfully diverse array of 18th and 19th century architectural styles just from exploring the immediate local area.

From pristine Georgian symmetry to palladian style windows of the Federal architectural style and of course colonial revival, which is is encapsulated by the Marsh Billings Rockefeller house in the park.

All you need to do is walk around The Green, Elm Street and Central Street for an architectural feast.

The entirety of Woodstock Village Historic District is listed on the National Register of Historic Places, which says enough in itself. You just know this is going to be a remarkably charming town.

Don’t miss the Norman Williams Public Library, a beautiful building open to the public just off The Green.

9. Walk Around Woodstock Town Shops

Shopping might be the last thing on your mind when visiting a quaint town such as Woodstock, Vermont. However, shopping here is a much more relaxing experience than a typical day at the mall.

Small independent stores, bookshops, galleries, farmers markets and quaint cafes are perfectly arranged along two very pedestrian friendly streets in town.

The best part? You won’t find a tacky gimmicky gift shop in sight.

Supporting local businesses is paramount to the continued prosperity in a touristy town like Woodstock. Don’t be shy about popping in for a coffee at Mon Vert or Soulfully Good.

The one place you should definitely check out is F.H. Gillingham and Sons. We were instantly drawn to the general store simply from its exterior, but inside we found an incredibly wide range of products in a traditional and historic setting.

This family run business is still to this day run by the 5th generation since opening in 1886. It’s next to impossible to walk around and not buy something!

10. Be Wowed By Radiant Fall Foliage

As you can clearly see from our photos in this guide to the best things to do in Woodstock Vermont, we visited in Autumn for the fall foliage season.

You can visit any time of year and you will still get the same experience of a picturesque and charming town. But the colors in fall just elevate its staggering beauty to another level.

Our best advice when visiting Woodstock in fall is to explore every nook and cranny of the entire region. Let’s say within a 10 mile radius of the town.

You will find classic and iconic fall images, but you will also find unique takes on Woodstock in the Autumn by exploring off the beaten path. Visit all of the even smaller villages nearby, walk along rivers and find elevated positions to look back on the town.

With that said, if you’re not up for a drive, the town of Woodstock itself has more than enough trees to enjoy those fiery autumnal colors of the fall season.

You also can’t miss Manchester VT in the south of the state if you’re looking for more special fall colors. Manchester is located in the heart of Green Mountain National Forest, which means rolling hills of vibrant Autumnal foliage for miles.

11. Woodstock Vermont Photography Locations

This will not surprise you – When we visited Woodstock in October, every single person we saw had a camera. Even if you just use your smartphone, we can guarantee you will leave Woodstock with hundreds of gorgeous images.

So, where should you go with your camera to take home the best photos?

Well, you should start with the two farms we talked about earlier, Jenne Road Farm and Sleepy Hollow Farm are not to be missed. Next, the town of Woodstock is extremely photogenic so get busy with your camera in town.

After that, you have all of the covered bridges near Woodstock to check out. They include Woodstock Middle, Quechee, Lincoln, Tafstville and even Cornish-Windor.

There’s a lookout point near Mount Tom with exceptional views over the town of Woodstock, which in Fall are just so impressive.

But our advice is the same as before, jump in the car and drive around the narrow country roads. Try to find something new, maybe a road with colorful trees arching overhead or another covered bridge not listed on every single article online.

Don’t forget you can use your drone around rural parts of Vermont as long as not within 5 miles of an airport. This works great in Fall.

We stumbled across possibly the most stunning covered bridge when driving to Jenne Road Farm. It was just off the road leading into a private property but we hadn’t read about it beforehand.

You can see this bridge in our favorite 7 covered bridges to see in Vermont .

What beautiful but unique photograph will you find around Woodstock?

12. Best Hikes Near Woodstock, Vermont

Most visitors to Woodstock will pass through in a day or maybe two, which makes finding time for a hike difficult. Especially when there are plenty of awesome hikes in other parts of Vermont, such as the awesome town of Stowe in the North.

However, for those who do have the time available for a hike on a longer visit, you have a handful of great hiking options right near town.

Don’t forget about Quechee gorge as mentioned above and remember, Woodstock is very close to the Appalachian Trail.

Mount Tom and The Pogue – The most popular hike in Woodstock is within Marsh Billings Rockefeller National Historic Park. You can access Mount Tom via multiple entrances and trailheads but we would suggest starting at the parking lot for Billings Farm and Museum. The full loop including both The Pogue (pond) and Mt Tom (Woodstock town views) is just over 4 miles with 650 ft elevation gain.

Mount Peg – This short 1.3 mile roundtrip loop gains around 300 ft in elevation to provide views looking back over Woodstock, but this time from the South side of town.

Luce’s Lookout – Set your google maps for ‘The Lookout Trailhead’ and drive a quick 8 miles north up VT-12 before turning onto Greengate Road. This is a 2.5 out and back trail with old lookout at the top providing more excellent valley views.

Woodstock Aqueduct Trails – This time set your google maps for ‘Aqueduct Trails’ and a 2.7 mile drive through West Woodstock will bring you to the trailhead. You can choose how far to hike through forest with boardwalks. Be aware that this is primarily a mountain bike trail.

13. Dartmouth College and King Arthur Flour

Have you ever looked around the campus of an Ivy League university? Why not take the opportunity when visiting Woodstock and just 20 miles from Dartmouth College?

Dartmouth is actually just inside the New Hampshire border in Hanover on the other side of the Connecticut River. The Ivy League college is the ninth oldest US institution of education, welcoming students since as far back as 1769.

Conveniently, the King Arthur Baking Company sits right on the other side of the bridge connecting the two states. Have you ever baked with King Arthur flour? It makes magic happen in the kitchen!

But what can you do a the King Arthur flagship campus?

Well, you can take a class in the baking school, watch expert bakers making bread and pastries, eat breakfast or lunch, shop for an array of baking recipes and of course accept every free sample.

See more information about visiting King Arthur Baking Company .

14. Marsh Billings Rockefeller National Historic Park

We have referenced this park a few times throughout this list of the best things to do in Woodstock, Vermont but now it’s time to get into more detail about the Marsh Billings Rockefeller National Historic Park.

Run by the NPS (national park service), this 643 acre plot of land is named after all of the previous owners of an old dairy farm and forest.

The land was transferred by the Rockefellers to the NPS in 1992 and in doing so gave Vermont its only unit within the US national park system.

You already know about the loop hike beginning and ending at the Billings Farm lot, via The Pogue and Mt Tom, but there are many more things to do once inside the park.

You can take a guided tour of the magnificent Marsh Billings House, walk under 400 year old trees on pristine Vermont carriage roads, bird watch, take a woodland workshop or cross country ski during Winter.

Be sure to check the park calendar for any upcoming events for your dates of visiting Woodstock.

Find more information including maps of Marsh Billings Rockefeller Park here .

15. Stay At The Impressive Woodstock Inn

The Woodstock Inn is the place to stay in town if you’re celebrating something special or have one final splurge in your New England road trip travel budget.

From both the outside and inside, the Woodstock Inn oozes class. It is perfectly located right in the center of The Green in town, ideal for walking to everything you might need throughout your stay.

>> Book Woodstock Inn : Direct | Booking.com

The Woodstock Inn isn’t cheap, but there are plenty of other lodging options to stay at during your time in Woodstock.

You can either read our complete guide to the 7 best hotels in Woodstock VT on our sister site Best Hotels Anywhere, or click on any of the top rated hotels in town below to see availability for your dates:

• The Village Inn of Woodstock
• Sleep Woodstock Motel
• 506 on the River Inn Woodstock
• The Woodstocker B&B
• Woodbridge Inn B&B
• Jackson House Inn

Map Of Best Things To Do In Woodstock Vermont

• Red Markers – Locations of the best things to do in Woodstock Vermont.

Click or touch the map to activate.

Zoom in and out, move around the map of Woodstock VT to find locations of the best things to see and do in the area.

More From Vermont

• 15 Best Things To Do In Stowe, Vermont
• 15 Things You Can’t Miss In Manchester, VT
• 10 Best Things To Do In Burlington VT
• 7 Stunning Covered Bridges To See In Vermont

Discover the 10 best places to visit on a New England Fall Foliage Road Trip with itineraries covering 5 days, 7 days and 10 days.

More From New England

• 17 Amazing Things To Do In Acadia National Park
• 13 Best Stops Along Kancamagus Highway Road Trip NH
• Flume Gorge NH Waterfalls And Covered Bridges Hike

We hope this guide to the best things to do in Woodstock, Vermont helps you plan your visit!

Have you been to Woodstock? What were your favorite things to do in the area?

Please let us know if you have any questions or need any help planning your visit in the comments below.

Happy Travels ,

Mark and Kristen

Was This Post Helpful? Pin It For Your Visit!

Note : This article contains affiliate links. When you make a purchase using one of these affiliate links, we may earn a small commission at no extra cost to you.

All Rights Reserved © Where Are Those Morgans, LLC. Republishing this article and/or any of its contents (text, photography, maps, graphics, etc.) in whole or in part is strictly prohibited.

Mark and Kristen Morgan are travel, hiking and photography experts. Over the last 6 years traveling full time, they have explored more than 40 countries and 30 US states.

Where Are Those Morgans has been featured in USA Today, Gestalten, Get Your Guide, CityPASS and Condé Nast Traveler along with various other publications. Read more about us .

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20 Awesome Things To Do in Woodstock, Vermont in 2024

March 14, 2024

Paula Martinelli

What are the best things to do in Woodstock VT?

If you are planning a perfect Vermont itinerary and wondering what things to do in Woodstock, VT that you cannot miss, you are in the right place! After spending some time exploring Vermont , I am here to share the best things to do, and my top tips!

Woodstock is a small, quaint town with plenty of things to explore in town and the surroundings. It is one of the best gateways in Vermont , and one of the most beautiful towns to visit in the United States , for a reason. And it won’t disappoint you!

There are a lot of great places to check out in Woodstock, no matter when you visit it. Whether you like being active outdoors or prefer shopping, relaxing, and enjoying farm-fresh food, or go on a romantic gateway to visit the most beautiful covered bridges in Vermont . You will find something for everyone in this charming town.

This guide to the best things to do in Woodstock VT is  packed with very helpful tips , plus the best places to stay, and the must-visit breweries and restaurants in town. So, without any further ado, let’s explore the best of Woodstock Vermont!

You will also love ❤️ :

• Perfect Vermont Road Trip Itinerary
• 15 Amazing Cabins you can Rent in Vermont
• 15 Most Fabulous Inns & Boutique Hotels in Vermont

14. Visit Billings Farm & Museum

20. golf at woodstock country club, what to pack for woodstock, vt.

Essential Tips for Visiting Woodstock, VT

❄️ If you are wondering how many days you need to visit Woodstock, I recommend spending 2-days and 1-night to take full advantage of all the things you find to do in Woodstock and its surrounding

❄️ Woodstock is one of the most popular destinations in Vermont, so make your hotel reservations in advance as it may be hard to find last-minute accommodations

❄️ I recommend booking your stay at the incredible  The Woodstock Inn & Resort   and a great budget option is the   Woodstock Bed and Breakfast – Also, in Woodstock you can find the best inns & boutique hotels in Vermont .

❄️ If you are looking for a romantic gateway, there are amazing cabins you can rent in the Woodstock area.

❄️ Woodstock is a very small town and you can find plenty of parking spots.

❄️ Driving a 4×4 car during wintertime in Vermont is not necessary, but it is nice to have if you are planning to drive outside the town.

❄️ You don’t need a car if you are only visiting the town of Woodstock, as you can walk around. But if you are visiting other places outside Woodstock I recommend to rent a car. You can save on your rental car when you book through this site . I use and recommend Discover Cars because it is the most reliable rental car source, and it allows you to compare the prices of different places.

15 Best Things to Do in Woodstock, VT

1. admire the classic new england architecture in woodstock.

This comes to the top of my best things to do in Woodstock, VT as this is the reason that many (including myself) visit this city. Woodstock is considered one of the most beautiful cities in America for a reason. And it won’t disappoint you!

You will love taking a stroll down Main Street in Woodstock, and just get lost admiring the stunning array of buildings of 18th and 19th-century architectural styles. The best streets to mark on your map are The Green, Central Street, and Elm Street to get mesmerized by the beauty of Woodstock.

Some of the most classic and beautiful buildings in Woodstock are the Normal Williams Public Library and the Woodstock Inn.

Woodstock is a great place to visit all year long, but it turned into a magic place during wintertime when the town is decorated, making it look like you are inside a movie. Here you can also find local artists, craftspeople, and purveyors that capture the Vermont winter wonderland spirit.

2. Visit one of Woodstock’s Covered Bridges

One of the best things to do in Woodstock is to visit its covered bridges . Vermont is well-known for these iconic bridges, and a few of the best ones are in Woodstock.

Middle Covered Bridge is in downtown Woodstock, so it’s an easy place to visit when you’re in town. It’s one of the most popular covered bridges in the state, and it’s a great one to take pictures with.

The other covered bridge in Woodstock is the Taftsville Covered Bridge , east of downtown Woodstock. It is a vibrant red bridge, and it is worth taking a quick drive, or even a bike ride, to visit the bridge when you’re in Woodstock.

Do you love covered bridges? Vermont has many of them, and I have a list of the 20 best-covered bridges in Vermont .

3. Visit the Sugarbush Farm is one of the best things to do in Woodstock, VT

Vermont is well known for having fresh farm food, and Woodstock is no exception. The first thing I recommend doing in Woodstock is visiting Sugarbush Farm . The farm is about 15 minutes by car from downtown, and it’s one of the best things to do in Woodstock, VT.

This farm is best known for their cheeses and maple syrup that they make on-site, and when you visit, you get to try all the samples of their cheeses and maple syrup! Their food is so good that you’ll have to stop in the farm store where you can buy cheese, syrup, jams, meats, and more, which are all grown and made on the farm or locally in Vermont.

Take a self-guided tour of the farm to learn how they make their maple syrup and meet the goats who live on the farm.

4. Marsh-Billings-Rockefeller National Historical Park

Another one of the best things to do in Woodstock, VT that I recommend is visiting the Marsh-Billings-Rockefeller National Historical Park . The park is one of the prettiest places in Vermont, and it’s a great place to walk through with all the maple trees, covered bridges, and stone walls.

There is also a Mansion on the park grounds that you can tour in the summer and learn more about the park’s history. You can join other guided tours as well, like a behind-the-scenes look at the park and other interesting history tours, but plan ahead as they tend to book up.

5. Learn about Woodstock at the History Center

Are you a history lover? Woodstock is full of history, and going to the Woodstock History Center is one of the best things to do during your visit.

There are a few areas of the center to visit, including a house from 1807 and a library containing a lot of information on the town’s history. There is also a beautiful outdoor garden area that is especially great if you visit in the spring or summer.

It’s easy to visit the historic center as it is in the middle of town.

6. Don’t Miss the Fresh Food in Woodstock

No list of best things to do in Woodstock VT is complete without mentioning food! Vermont is known for its farm-to-table style. Fresh eggs, vegetables, and organic meat are pretty iconic foods in Vermont that you will see often. And some cafes and restaurants in Woodstock downtown offer the opportunity to try some amazing farm-to-table food. Here is my top pick for you:

• Mon Vert Café  is an organic breakfast and lunch spot right in the heart of Woodstock. Local, country, and rustic all wrapped up in one, here is a perfect spot to start your day. Serving breakfast options all day, you can grab a fancy cappuccino and a breakfast sandwich.
• Worthy Kitchen  puts heart and soul into local food and drink. Here you can find delicious farm-to-table comfort with an ever-expanding menu featuring locally farmed ingredients. In addition, constantly rotating beer selections showcase Vermont’s strong influence on the craft beer movement.
• Richardson’s Tavern  is just the spot if an upscale, cozy tavern is more your style. Dine fireside, or sink into an overstuffed chair with an evening cocktail before dinner. The Tavern is only open daily from 5 p.m. to 9 p.m.
•   Lincoln Inn & Restaurant,  where chef Jevgenija Saromova takes years of restaurant training in Italy, England, and France and applies them to the seasonal flavors of Vermont.

PRO-TIP: If you are into the local brewery, you can also choose to go on a Classic Beer Tour with tasting and lunch to taste the best of Burlington. Or you can join the Stowe half-day local brewery and food tour.

7. Relax at the Woodstock Inn Spa

If you are biking or hiking in Woodstock, you’ll need a spa day to give your body a rest. The Spa at the Woodstock Inn & Resort is a new spa with lots of different services and features for you to enjoy.

There are great treatments for everyone to enjoy at the spa, including nails, massages, body treatments, and facials.

PRO-TIP: It is recommended scheduling treatments in advance to ensure that your preferred time and service are available. Appointments can now be  Scheduled Online  seven days per week. Also, I highly recommend booking your stay at the Woodstock Inn to complete your special visit to Woodstock.

8. Stay at the Most Beautiful Address in Woodstock

This elegant building offers 142 guest rooms and suites and is perfectly located in the heart of Woodstock, this is definitely one of the top things will need to do while visiting Woodstock.

The luxurious Woodstock Inn & Resort   is a stunning classic New England style that boasts Vermont craftsmanship at every corner of the building, allowing the guests to immerse in the timeless and classic Vermont-style accommodations.

The Inn has been recently remodeled, offering fresh and unique rooms, with a roaring central fireplace and an airy spa with its own countryside hot club.

PRO-TIP: Here in Woodstock you will find the some of the most beautiful inns & boutique hotels in Vermont, so take advantage while you are visiting to experience the all the charm that you can find on these classic New England style accommodations.

9. Woodstock Nordic Center

One of the best places to spend a winter’s day in Woodstock is at the Woodstock Nordic Center . The center has 28 miles of trails groomed for skating, cross country skiing, snowshoeing, and fat-biking.

There is a fee to enter the center, and they also offer equipment rentals if you need them. If you are new to winter sports, they also offer lessons so you can learn how to ski properly, or you can get a guided tour of the area either by skiing, snowshoeing, or biking.

10. Visit the Kelly Way Gardens

The next great thing to do in Woodstock is to visit the Kelly Way Gardens . In the gardens, they grow hundreds of varieties of vegetables and flowers and herbs, berries, and orchards in a 3-acre garden. The food goes straight to the kitchen for chefs to make the freshest farm-to-table food.

At the gardens, you can take a tour to see how the operation works and enjoy the tastings of the foods they grow. You can also enjoy a meal or take a cooking class.

11. Have a fine dinner at the Lincoln Inn and Restaurant

Voted one of the best restaurants of 2016, the Lincoln Inn Restaurant and Tavern offers unparalleled fine dinning experience, with meals prepared gourmet-fusion plates that involves all the senses, prepared by the talented European Michelin Star trained Chef Jevgenija Saromova.

If you appreciate good high quality food, one of the best things to do in Woodstock is to visit the Restaurant and Tavern at the Lincoln Inn for a remarkable and memorable culinary experience.

PRO-TIP: I really recommend you to have the Chef Tasting Menu, with a 7-course, including 7 tasting glasses of wine each paired perfectly for each course.

12. Shop in Downtown Woodstock, VT

Downtown Woodstock is a cute place, and another great thing to do here is to spend some time shopping. There are dozens of unique shops in the town. Some shops include gift shops, clothing stores, book stores, boutiques, and home goods.

In Woodstock, you will be able to visit the great variety of the to specialize in this sort of artisan shops with beautiful, art-quality work, with prices to match. One of the best stores to visit is the Collective, with a great collection of craft-type items available to choose from.

13. Woodstock Farmers’ Market

One of the best things to do in Woodstock in the summer is to visit the Woodstock Farmers’ Market . The farmers’ market is only a mile and a half from downtown Woodstock, so you can easily drive or bike there.

At the Woodstock Farmers’ Market, you’ll find a huge variety of fresh produce, meats, dairy, and much more food that is locally grown and made. The market is also a great place to grab some lunch, as they have a stand that sells sandwiches, soup, salads, and even grab-and-go entrees, which are easy to heat up for dinner.

A cool place to visit in Woodstock, VT, is Billings Farm & Museum. No matter how old you are, you’ll love the dairy farm. And, it’s easy to visit the farm because you can walk to it from the Woodstock town center.

The dairy farm is fully operating, and you get to see a lot of cute animals when you visit. Most of the animals are Jersey cows for milking and their calves. But, there are also horses, pigs, steers, goats, sheep, and chickens.

Other than the animals, there are educational exhibits and activities. And depending on when you visit, there are a lot of special events at Billings Farm, like exhibitions and dairy celebrations.

PRO-TIP: If you are visiting Woodstock during the holiday festive, one of the most popular is the Wassail Weekend, a weekend event held at the Billings Farm, a wonderful dairy farm and museum. The event normally happens during the second week of December, when they recreate the historic New England Christmas charm. 

Outdoor Things do in Woodstock VT

15. go ski at the suicide six ski area.

Another one of the best things to do in the winter in Woodstock, Vermont, is to snowboard or ski at the Suicide Six Ski Area . They have mostly easy trails, but there’s a place for beginners and more experienced skiers and snowboarders alike.

And, the fun doesn’t stop in the winter! In the summer, you can visit the area in Woodstock and mountain bike on the trails.

PRO-TIP: Don’t forget to check the sky conditions to find out the best ski areas.

16. Hike Mt. Peg or Mt. Tom

Woodstock, VT, has two great mountains for hiking: Mt. Peg and Mt. Tom. Both are easy to get to from Woodstock, with Mt. Peg just south of the town and Mt. Tom just north.

Mt. Peg is the easier one to hike with a simple 1.7-mile loop. The trail has great, vast views of Woodstock and the surrounding areas. Mt. Tom is also an easy hike, but the trail is longer than four miles for the loop. There are many signs to follow that will lead you to beautiful views of Vermont.

PRO-TIP: If you are planning to visit Vermont in winter , keep in mind that the weather conditions may change quickly, so be sure to bring a warm jacket , extra snacks, and plenty of water. Depends where you decide to go hiking and the distance, you can also get help from snowshoes.

17. Learn about Birds at the New England Falconry

One of the unique things to do in Woodstock is to visit the New England Falconry . At the falconry, you can learn about the history, conservation, and lives of birds and raptors. And you’ll, of course, get to see some birds in action, like the free-flying Harris hawks who live at the falconry.

18. Explore Woodstock, VT by Bike

Taking a bike tour of Woodstock, Vermont, is one of the best ways to fully experience the town. And joining a tour with Discovery Bicycle Tours is one of the best ways to make sure you do all the best things you can do in Woodstock, VT.

The bike tours are best if you have a week to spend in Woodstock, as their tours are six days long. Their first Woodstock bike tour is a Multisport Bike Tour that includes biking, hiking, and visiting Billings Farm and Sugarbush Farm. Not only will you see how beautiful Woodstock is, but you get to visit some of the great places I recommend on this list.

Or, you can take the Woodstock Self-Guided Bike Tour , which has fewer scheduled activities, but you still get to bike, hike, and kayak. And these bike tours include your lodging and some meals, making your trip planning easy.

19. Explore the Quechee Gorge and Village

When you search for things to do around Woodstock, VT, you will find many things in Quechee, VT since it is less than 15 minutes away driving. The Gorge is an awe-inspiring natural formation, making it one of the top things to do around Woodstock, VT.

If you are driving, you will find a parking area just beyond the Quechee Gorge bridge , and the bridge has a sidewalk with rails, so you can safely walk out and peer into the gorge.

PRO-TIP: While you are visiting the Quechee village, I recommend making reservations to have dinner at The Mill, voted one of American Most Romantic Restaurants. The food is amazing, cooked with local fresh ingredients, with very creative cuisine, and a stunning backdrop of the Ottauquechee River waterfall and covered bridge.

The last thing to do in Woodstock, Vermont, that I highly recommend is playing a round of golf at the Woodstock Country Club. While golf may not be your thing, the country club is a great place to try it out. And, it was rated the number 1 golf course in New England by Golf Advisor, so you know it’s a pretty, well-maintained place.

Best Places to Stay in Woodstock, VT

You will find amazing options of accommodations in Woodstock, from cozy and romantic cabins to some of the best inns & boutique hotels in the State. If you are traveling without a car, I recommend choosing a location in the city center, as you can explore Woodstock by foot. Below are my top choices for you:

Top Overall: Jackson House Inn

Rated: 9.6 Exceptional

The Jackson House Inn  is situated in a fabulous location in Woodstock, and the extra comfortable rooms are designed with space in mind. Also, with a bar on-site and a tasty breakfast is included.

Great Location: The Woodstocker B&B

Rated: 9.7 Exceptional

The Woodstocker B&B is a fantastic choice if you’re looking to stay in Woodstock. It’s an adult-only hotel so is perfect for a romantic getaway without the children! You’ll also be close to Woodstock town center and there are plenty of opportunities for skiing and horse riding in the surrounding area.

Luxury Option: Woodstock Inn & Resort

Rated: 8.6 Fabulous

This is undoubtedly one of the most luxurious boutique hotels in Vermont! Woodstock Inn & Resort is a huge hotel that offers a wide variety of room options. It’s also in a great location as it’s situated close to Marsh-Billings Rockefeller Park and the Billings Farm Museum.

Woodstock, VT Frequent Asked Questions

What is the best time to visit woodstock, vt.

FALL: It is the most popular time of the year to visit Woodstock because it is when the fall foliage happens from early October to around the third week of the month. It is important to plan in advance, especially make your accommodations in Woodstock well in advance. Prices for hotels and flights will be most expensive during these months.

WINTER: The fact is that the whole state of Vermont is cold in winter – with temperatures that can drop below zero. But as long as you pack accordingly, you will love it because the snow makes Vermont’s landscape look and feel even more spectacular! Make sure to check the weather , and have fun on the snow slops around Woodstock!

SUMMER: During summer time Woodstock offers great outdoor eateries, swimming holes and great brewery to enjoy the outdoors. The warmest time of year is generally mid July where highs are regularly around 84.9°F (29.4°C) with temperatures rarely dropping below 59.5°F (15.3°C) at night.

SPRING: Spring is a beautiful time to visit Woodstock, plus it is a perfect time to visit for some quiet and peaceful getaway. There are many things to do outdoor that will allow you to enjoy, such as the maple syrup flowing, enjoy the spring wild flowers and drink a local beer seating outside around a fire pit.

What is the best way to get to Woodstock, VT?

Woodstock is a 15-minute drive from Vermont Interstate 89. Take Exit 1 to Route 4 West. Follow Route 4 West directly into town. If you’re flying, the closest airport is  Burlington International  (BTV). Approximately 90-minutes from Woodstock.

You will need a car to explore the surroundings of Woodstock.  You can save on your rental car when you book through this site . I use and recommend Discover Cars because it is the most reliable rental car source, and it allows you to compare the prices of different places.

Make sure you are prepared, considering the season and the activities you are planning to do. Here are some quick tips:

• Pack layers are the best you can do!
• Bring a pair of jeans a light sweater to wear in the evenings
• Pack rain gear – you don’t want to get soaked wet while exploring
• A hat, gloves, and scarf  can’t go wrong, even in summer.
• If visiting in winter, bring good quality sturdy snow boots .
• Bring warm leggings to wear as a layer is a smart choice!
• Pack a good , check my complete review guide on the Top Jackets for Travel
• If you are planning to carry a backpack for your trip to Vermont, I have compiled a very detailed review of the Best Backpacks for Travel on the market today

Things to do in Woodstock, VT Conclusion

I believe that everyone should visit Woodstock, VT once in a lifetime!

There are many great things to do in Woodstock, Vermont, year-round. In the summer, you can hike, golf, and bike outside or enjoy one of the farms and natural areas. Or, in the winter, you can shop, relax at the spa, and visit one of the town’s covered bridges, which are pretty when covered in snow.

If you have any questions or anything I am missing in this list, please let me know in the comments below.

You may also enjoy reading:

• 15 Most Amazing Cabins you can Rent in Vermont
• 15 Best Inns & Boutique Hotels in Vermont
• Winter Vacation in Vermont: 10 Perfect Winter Getaways!
• 20 Most Beautiful Covered Bridges in Vermont
• 13 Awesome Things to do in Stowe in winter
• Terrific Things to do in Burlington in winter
• 19 Awesome Things to do in Vermont in Winter

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Winter Vacation in Vermont: 10 Best Vermont Winter Getaways

A Perfect Vermont Road Trip Itinerary in 2024

20 Awesome Things to do in Vermont in Winter of 2024

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16 Incredible Things to Do in Woodstock VT (2024 Guide)

Searching for the best things to do in Woodstock VT? You’ve ended up in the perfect place to find all the inspiration and travel advice you need!

Did you know that Woodstock VT is considered the prettiest town in the US? Multiple publications share that sentiment which is saying something!

Although this photogenic town is compact and small, that’s not to say there aren’t masses to keep you busy. Plus, the farmland, forests, and state parks surrounding Woodstock are essential to factor into your plans.

So where to go and what to do in Woodstock? Read on for the complete list of the best places to visit in Woodstock VT plus essential advice for planning your trip.

* Disclosure: This post contains a few affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through my link. *

No time to read now? Pin it for later!

Table of Contents

Useful Info for Visiting Woodstock VT

How to get to woodstock, vermont.

Officially speaking, Lebanon Airport (LEB) is the closest airport to Woodstock. It’s located 15 miles (24 km) to the east in the state of New Hampshire. However, you’ll find that flights from international airports require transit via a larger port.

Burlington International Airport (BTV) is well-served by national US cities. If you are planning what to do in Woodstock within a wider New England road trip then you could always start here in northern Vermont.

In terms of the best option for travelers beyond the US, your best bet is Boston Logan International Airport (BOS). Located in the city of Boston, Massachusetts, this large airport is the best place to start your search for flights from Europe and other worldwide destinations.

Best time to visit Woodstock, Vermont

Woodstock is a year-round destination where each season brings a new selection of activities to choose from. 

In terms of scenery, places to visit in Woodstock VT are particularly special during the fall season when the foliage turns to hues of gold, amber, and scarlet. Bear in mind that this is a popular time to visit Vermont and New England so you will need to book accommodation in advance.

Mid-spring and early summer is a great time to visit Woodstock if you want to explore the local hiking trails and beat the summer rush. 

Meanwhile, the winter snowfall is perfect for skiers, snowboarders, and sledding enthusiasts. Remember that most state parks and some roads are closed to the public during winter. You may need to rent a 4X4 and take into account other seasonal precautions in order to drive safely. 

How to get around Woodstock VT

Woodstock town itself is walkable and there are a handful of sights to see in the center. However, the best things to do in Woodstock VT aren’t always constrained to the town center!

Realistically, you will need to hire a car in order to explore the area around Woodstock. Public transportation in the New England region is limited and taxis are costly if you want to explore the surrounding towns and parks. 

Roads around Woodstock are in fantastic condition while parking is aplenty, so hiring a car and driving around this beautiful area is a blast.

Where to stay in Woodstock, Vermont

Hotels, guest houses, and inns are located in the town center of Woodstock as well as the surrounding area.

If you stay in town, you can enjoy having the restaurants and amenities on your doorstep with no need to drive. Staying further afield is perfect if you want more of a countryside vibe. 

A word of warning: places in Woodstock VT get booked up months in advance so you’ll definitely need to organize yourself in plenty of time. This is especially true if you visit during summer or the fall foliage season!

LUXURY – 506 On the River Inn Woodstock

Centrally located with an indoor swimming pool and sauna, this is the perfect luxury base for your Woodstock VT activities. All boutique rooms are fitted with a private balcony and en suite bathroom. Studios come with a personal kitchen. 

MID-RANGE – The Shire Woodstock

This pet-friendly hotel is situated on the banks of the Ottauquechee River. Each guest room is appointed with traditional New England furnishings and many offer a river view. Scenic, comfortable, and convenient!

BUDGET – The Vesper Woodstock

Located just off the Village Green, this Greek Revival home is furnished with antiques, oriental rugs, and a collection of art. Rooms are bright and cheerful with a private bathroom. Breakfast is included in the rate.

Best Things to Do in Woodstock VT

Let’s dive into the main part of the guide – all the fabulous and unforgettable things to do in Woodstock Vermont!

1. Explore Woodstock Central Street and The Green

The heart of Woodstock is defined by Central Street and The Green. This walkable center is bursting with cafes, restaurants, and small independent boutiques where you can pick up books, jewelry, and trinkets. 

Whatever you do, make sure that unwinding with a coffee is one of the high-priority things to do in Woodstock VT!

Dishing up organic breakfasts and excellent coffee, Mont Vert Cafe features a gorgeous patio as well as a homely interior. Right next door, Soulfully Good Coffee is the place to go when you’re craving waffles, croissants, and freshly baked treats. 

Have a wander down to the Woodstock Town Hall Theatre. Originally an opera house, this neoclassical manor now hosts a variety of musical events as well as performance theater and movie screenings.

It’s worth checking the schedule to coincide with your trip in case you fancy doing something fun in the evening. 

2. Tour the Woodstock History Center

This is one of the first places to visit in Woodstock VT in order to get a handle on the local and regional history. Exhibits change frequently and tell the story of the people that have dwelled in and shaped Woodstock.

Artifacts on display include paintings, photographs, books, and objects. It’s a small collection but utterly worth a visit so that you understand more about the area.

The Woodstock History Center is located on Central Street and is open from Monday to Friday. 

3. Walk to Woodstock Middle Covered Bridge 

Vermont and the wider New England region are famous for their covered bridges. These historic structures were, on the whole, constructed during the 19th and 20th centuries. 

There were several reasons behind their construction. For starters, they averted the risk of flooding caused by heavy snowfall in the region.

Additionally, they would provide safe shelter for pedestrians caught in storms and make local farmers’ lives easier when herding livestock. 

Now – in the 21st century – these relics from the past have blossomed as major tourist attractions. The Woodstock Middle Covered Bridge staddles the Ottauquechee River and is one of the most beautiful bridges of its kind in the region. 

This one was only built in 1969 although the engineers used historic techniques in order to replace the original bridge. The result is that it looks a lot older than you might think! This bridge is special as it features a separate walkway for passengers to walk safely alongside motor vehicles. 

Best of all, this is one of the Woodstock VT attractions that you can visit in town without the need for a car. 

Read More: 17 Incredible Covered Bridges in Vermont You Need to Visit

4. Stock up at the Woodstock Farmers Market

Woodstock Farmers Market is located one mile west of the town. It’s open Tuesday through Saturday (closed on Mondays and Sundays) and is attached to a seasonal garden center.

The market sells fresh grocery produce, dairy and eggs, meat and seafood, baked goods, and specialty pantry items. Everything is sourced and produced in the Woodstock area and Vermont. You also pick up pre-made artisanal sandwiches to go. 

The farmer’s market opens at 8 am and it’s a great place to pick up your essentials before embarking on a day trip while supporting local businesses.  

5. Snap a sunrise photo of Sleepy Hollow Farm

Sleepy Hollow Farm is a private farmstead consisting of russet-red outhouses and barns just outside of the town. This photogenic farm is set against a backdrop of Vermont hills and forestry. 

Its first recorded owners were a pair of brothers from the 18th century. After a couple of centuries of work, the last surviving relatives ended up selling the farm in the 1950s.

For a couple of years, Sleepy Hollow passed through a series of hands. It continues to be privately owned, however, it is possible to drive up to the premises and take photos.

As one of the most popular things to see in Woodstock VT, you should arrive there first thing in the morning if you want to avoid a long line of cars. This is especially true if you ’re visiting Vermont in the fall !

​​Sleepy Hollow Farm is located a 15-minute drive north of Woodstock on Cloudland Road – a long gravel dirt track that winds through the countryside.

2023 UPDATE: Unfortunately, access to Cloudland Road will be limited to locals only starting from 23 September to 15 October, so if you’re visiting during this period, you won’t be able to see the farm in person.

6. Sample cheese and maple syrup at Sugarbush Farm

Another farm to add to your list of things to do near Woodstock VT! Sugarbush Farm is a 500-acre farm owned by a local family that produces some of the best cheeses and maple syrups in the area.

The Luce family eagerly welcomes visitors to tour the farm, walk the nature trail through the woodlands, and browse the farm shop. Workshops operate an open-door policy so you can pop in and see how the cheeses and syrups are made. Not to mention, tastings!

It’s free to visit Sugarbush Farm although it’s polite to make a purchase from the farm shop to support the business. 

Sugarbush Farm is located a 15-minute drive out of Woodstock. 

7. Swing by the Instagrammable Jenne Road Farm

The next farm to add to your radar is super famous on social media. 

Jenne Road Farm consists of scarlet-hued outhouses and barns. This working farm is owned by a local family and has been in operation since the early 20th century.

Unfortunately, you can’t visit the farm properly and look around but you are permitted to stop by for a quick photo. Plus, you can pick up some of their maple syrup while passing through. 

Jenne Road Farm is one of the major Woodstock VT attractions to visit during fall when the colors dance behind the buildings. 

The farm is located 15-minutes south of Woodstock, off State Route 106. 

8. Explore Billings Park and Mount Tom

When you’re seeking outdoor and hiking pursuits, Mount Tom is the closest option to the Woodstock center.

The peak is located in Billings Park – a large green space that also contains the Marsh-Billings-Rockefeller National Historical Park. There are multiple hiking trails and walking paths within this complex of varying difficulty.

Mount Tom is accessible via a moderate 4-mile hike. The route has a noticeable elevation that your legs will feel although it’s not too challenging overall.

Once at the top, you’ll have a panoramic view across Woodstock. This is particularly special during the fall season when you’ll see all the different hues. 

The summit of Mount Tom is one of the best places to visit in Woodstock VT at sunset. The trail is accessible between April and October before the snow arrives. 

9. Visit the Billings Farm and Museum

Billings Farm and Museum is the final farm on your list of things to do in Woodstock Vermont that is a little different from the others.

For starters, it’s situated in the center of Woodstock so you can walk there easily without the need for a car. This farm is active within the community – it frequently hosts events and runs educational programs with nearby schools.

Tourists are welcome to visit the farm for a token admission fee. Once you’re in, you can wander around the barns, pastures, tractor collection, kitchens, and 1890s farm manager’s lodge. And, of course, befriend the resident animals. 

The farm is dressed with exhibitions and live demos that will enrich your understanding of agricultural practices in Woodstock, Vermont, and New England.

Billings Farm and Museum also offers a robust schedule of seasonal and special events throughout the year. 

10. Take in views from Mount Peg

Located on the opposite side of the Ottauquechee River, Mount Peg is another of the hiking places to visit in Woodstock VT.

It’s located in Billings Park (part two!) and easily accessible via a short and easy hike.

You’ll pass through a copse of woods as well as wide-open meadows before reaching the summit of Mount Peg. There are benches and picnic tables at the top where you can enjoy an al fresco lunch. 

As with Mount Tom, you’ll get a wonderful 360-degree view of Woodstock and appreciate this hike in particular at sunrise or sunset. 

Mount Peg is accessible year-round regardless of the season and it’s perfect for non-hikers as well as families with younger children.

11. Hike in Quechee State Park

Quechee is a small town located a 10-minute drive east of Woodstock. Its town center warrants a wander (especially so that you can see the Quechee Covered Bridge) but the highlight of Quechee is the state park.

Park up at the Quechee Gorge Bridge and take a look at the gorge known as Vermont’s “Little Grand Canyon”. 

Carved by glaciers during the last Ice Age, the gorge has a depth of 165 feet (50 meters). You can view it from the bridge and swing by the Quechee Gorge Visitor’s Center to see the exhibits on its history. 

While there, pick up some hiking maps for the state park. Quechee State Park is one of the best things to do near Woodstock VT for outdoors lovers. Trails take you through the forest surrounding the gorge and provide different viewpoints of the natural wonder. 

Quechee State Park is open seasonally, May through October. Check the specific dates for each year if you want to visit Vermont to see the fall as well as hit the state park!

12. Explore Coolidge State Park

Vermont’s largest state park is located 12 miles (19 km) to the southwest of Woodstock. As with Quechee State Park, the park is open exclusively from May until October. 

Hiking trails in the Coolidge State Park navigate various peaks and lead you to dramatic views across the Black River Valley and the Green Mountains.

There are a number of pools, reservoirs, and brooks which are perfect for helping you to cool down during the summer season. 

The forest provides a habitat for the likes of barred owls, moose, and even black bears. 

Coolidge State Park is known for its fantastic campgrounds so if you fancy spending a night in the wilderness while in Woodstock, this is the perfect place. There is a mix of campsites and RV hook-ups. 

13. Nibble on local cheese

All these sightseeing and outdoorsy activities will build up an appetite. If you like cheese, you’ll be right at home in Woodstock. The town is known for its cheeses and one of the top things to do in Woodstock VT is finding your favorite. 

I’ve already mentioned Billings Farm and the Woodstock Farmer’s Market which are two of the best places to try cheese in Woodstock. You can also visit Mac’s Woodstock Market , F. H. Gillingham & Sons , and the Vermont Farmstead Cheese Company . 

The latter is further out of town but it’s worth the drive if you’re a huge fan of trying different cheese varieties. 

14. Eat the best ice cream

Mountain Creamery is a small, independently owned ice cream parlor located a short drive out of Woodstock VT.

All ice cream is handmade and uses local flavors from the Vermont region, such as maple syrup and walnuts. You can create your own sundae to suit your tastes and add toppings such as Oreo cookies, Reeses Pieces, and fresh fruits. 

If you’re not a fan of ice cream, they also serve pies, smoothies, and frappes. 

The Mountain Creamery is a 10-minute drive from the Village Green. However, if you have time in your schedule, you could walk there along the side of the river. This will take around 90 minutes each way though.

15. Drive through Taftsville Covered Bridge

The Middle Covered Bridge is one of the top things to see in Woodstock VT but you might want to visit another bridge while you’re in the area.

Taftsville Covered Bridge is only a 5-minute drive east out of Woodstock. This is another structure that passed over the Ottauquechee River. It’s a vibrant shade of red and really stands out against the backdrop of green (or orange) trees. 

Constructed in 1836, the Taftsville Covered Bridge is actually one of the oldest of its kind in New England.

You can drive beneath it in your car but it’s worth parking up and wandering down to the riverside where you can see the waterfall that drops below the bridge.

16. Wind down in a Vermont brewery

And what to do in Woodstock if you love beer? Vermont is famed for its craft beers and fortunately, there are a couple of breweries within easy access of Woodstock VT.

Founded in 1989, Long Tail Brewing Company is located on the banks of the Ottauquechee River and provides a lovely setting to sip the latest selection.

The brand was inspired by the 273-mile (440 km) hiking trail that traverses through the nearby Green Mountains. They specialize in IPAs and you can buy their flagship selection year-round but they also craft seasonal blends.

Long Trail Brewing Company is a 10-15 minute drive from Woodstock. 

Harpoon Brewery Taproom and Beer Garden is located at the side of the Connecticut River and overlooks New Hampshire.

They have a huge beer garden which is perfect in the summertime while their heated cabins are preferential if you visit during winter. Beers are a mix of ales and lagers as well as ciders. Harpoon Brewery is known for its excellent woodfired pizzas and events. 

Situated in Windsor, Harpoon Brewery Taproom and Beer Garden is a 20-25 minute drive from Woodstock VT. 

Planning a trip to New England?

Then you might want to take a look at all our other travel guides about New England. I promise, they are just as awesome as this article was!

• The Perfect New England Fall Road Trip for 2 Weeks
• Vermont in the Fall: Travel Tips & Best Places to Visit
• 16 Incredible Things to Do in Woodstock VT
• 17 Amazing Things to Do in Stowe, Vermont
• 17 Incredible Covered Bridges in Vermont You Need to Visit
• 81 Amazing Vermont Quotes & Captions for Instagram

New Hampshire:

• Kancamagus Highway Fall Foliage Drive: 9 Best Attractions & Tips for Visiting

Massachusetts:

• How to Spend One Day in Boston: Itinerary & Best Things to Do
• 13 Best Day Trips from Boston You Can’t Miss
• Where to Stay in Boston: 8 Best Areas & Hotels
• 133 Best Boston Captions for Instagram (Quotes, Puns & More)
• 19 Spooky Things to Do in Salem MA in October
• How to Spend One Day in Acadia National Park
• The Perfect 2 Days in Acadia National Park Itinerary
• Acadia National Park in the Fall: Practical Info & Tips for Visiting
• How to Spend One Day in Portland, Maine
• 5 Prettiest Lighthouses in Portland Maine You Can’t Miss

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Things to Do in Woodstock, VT - Woodstock Attractions

Things to do in woodstock.

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• Things to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.

1. FH Gillingham & Sons General Store

2. Quechee General Store - Cabot Station

3. FARMHOUSE POTTERY, INC.

4. The Yankee Bookshop

5. Pleasant Street Books

6. The Vermont Flannel Company

7. On The Edge Farmstand

8. Danforth Pewter

9. Clover Gift Shop & Clover Apothecary

10. Ellaway's Attic

11. Taftsville Country Store

12. Woody's Mercantile

13. 37 Central Clothiers

14. Woodstock Sports

15. Fleurish Floral Studio & Store

16. sunday drive dispensary.

17. Red Wagon Toy Company

What travelers are saying.

Adventures in New England

A local's guide to savoring the history, culture, food and nature of the Northeast USA

Things to Do in Woodstock, Vermont

Oh, how I love Vermont! It makes me happy just thinking about it. It has gorgeous forests, charming towns, and inspiring artisan culture. Located in southern Vermont, the area around Woodstock is very convenient to the rest of New England, and this area embodies all that I love about Vermont .

If you are searching for romantic getaways in Vermont, this area is the place to visit– historical, artistic, and quaint.

I visited the area around Woodstock for a perfect fall weekend girls’ getaway. We stayed in South Woodstock, a village of Woodstock, in a friend’s home in a restored mill. We came at peak foliage season, which is the ideal time to visit the area, although there is great skiing for a winter visit as well.

My family also drove through this area on our road trip from Boston to Montreal and Quebec City .

Read on to plan your perfect Vermont getaway.

Table of Contents

Things to do in Woodstock, Vt

Day one of our weekend around woodstock, vermont, explore the village of south woodstock.

South Woodstock is a small village that is part of Woodstock. The village is tiny but also feels like an escape from reality. We started our day with a refreshing walk past the old houses to breakfast at the South Woodstock Country Store.

South Woodstock Country Store

Not only can you find unique goods and foods in this authentic country store, they serve inexpensive but scrumptious food at their take-out counter. They have tables to eat at where you can enjoy locals chatting. We enjoyed our egg sandwiches and the atmosphere so much that we came here both days for breakfast.

Exploring Downtown Woodstock, Vermont

We spent the first day of our weekend in Woodstock. This town has often been called “the prettiest small town in America” and the quintessential New England town– and for a good reason. Walk along the main street, Central Avenue (Route 4), taking any deviations that excite you. The word meandering is made for this town, so that is what we did.

Shopping in Woodstock, Vermont

Around the town green in Woodstock, you will find many stores offering all your heart desires, from food and clothing to flowers and art.

FH Gillingham & Sons Vermont Country Store

You will find unique foods, clothing, games, and pet supplies in this country store. It is the perfect spot to pick up a souvenir.

Norman William’s Public Library

This public library is on the town green, with placards about the town’s history that are worth checking out. There is a used book sale in the alcove in front of the library, and I picked up one of my recent favorites, The Russian Concubine . Read about more of my favorite books .

Middle Bridge

You can’t come to Vermont without seeing at least one of the bridges it is so famous for– a covered bridge. There is one in town over the Ottaquechee River, Middle Bridge.

Dinner Around Woodstock, Vermont

Now that we had spent the day in town, we wanted to get away from civilization and see some spectacular views. We enjoyed the four-mile drive up the mountain to enjoy a farm-to-table gourmet meal at Cloudland Farm in North Pomfret. The farm has miles of Appalachian Trails, which are open to the public, so if you have time, you can earn your dessert calories with a pre-dinner hike. Reservations are required for dining.

One Day in Quechee, Vermont: Hiking and Art

For our second day in Vermont, we decided to explore the area around Quechee, specifically the artisans and the gorge. Our day started with egg sandwiches at South Woodstock Country Store before heading towards the Quechee Gorge for a short hike.

Vermont Antique Mall

We first stopped at the Vermont Antique Mall with a Cabot Cheese Shop.  You can also try locally-produced wines and fudge. Be sure to pet the alpacas behind the store.

Quechee River Gorge

Quechee Gorge is the deepest gorge in Vermont at 165 feet deep. There are fantastic views of the gorge from the bridge on Route 4 that crosses it. We took the pretty easy half-mile hike along the Quechee Gorge to reach the bottom. You can also camp here.

Woodstock Farmer’s Market

We stopped and grabbed lunch at the Woodstock Farmer’s Market. Although it is called a farmer’s market, it is more of a locally-sourced market with a deli counter. It won’t be a problem finding something yummy to eat here. The hard part is picking between all the great choices. We grabbed salads, sandwiches, and soups.

After lunch, we stopped by the see the Vermont artists at work.

Farmhouse Pottery

We stopped and watched the potters turn lumps of clay into beautiful cups and vases. You can buy the products in the store.

Andrew Pearce Bowls

Then we moved on to watching wooden bowls being made from local trees.

Sugarbush Farm

Another spot to try local foods- farm-made waxed cheeses and maple syrups!

The Mill at Simon Pearce

Everything about this mill set on the Ottauquechee River is magical. We started downstairs, where glassblowers are working hard to create some of the prettiest glass creations I have ever seen. Be sure to step out on the patio to see the Ottauquechee River waterfall, which provides power for the mill and flows right under a covered bridge.

The food in the dining room is American at its best, and the views are incredible. After dinner, we did some lustful shopping throughout the showroom.

Day Breaks Glass Studio

Try your hand at making stained glass with a class at this studio in Lebanon, Vermont.

Where to Stay in Woodstock, Vermont/ Woodstock, Vt Hotels

Woodstock inn & resort, woodstock, vermont.

Stay in the Woodstock Inn if you are looking for luxury right in downtown Woodstock. Even if you don’t have the money to stay, you should take the time to walk through the adorable inn. It is definitely one of my bucket list hotels.

Book your room at The Woodstock Inn now.

Quechee Inn at Marshland

If you are looking for more moderately priced accommodations, this colonial farm with many activities is a great option.

Book a room at the Quechee Inn now.

Kendron Valley Inn

This charming small hotel is right in South Woodstock. It has a fantastic upscale pizza restaurant. Pets are allowed in cabins behind the main hotel.

Book a room at the Kendron Valley Inn now.

Here is a map to understand where the things we did are in relation to each other:

As you can see, there are so many unique, charming, tasty outdoor things to do in southern Vermont–even if it is not winter with its nearby skiing!

Have you been to this area of Vermont? Please let me know about it in the comments if you have anything to add.

If you are visiting Vermont as part of a trip to New England, be sure to check out my Local’s Guide .

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6 thoughts on “Things to Do in Woodstock, Vermont”

We have been planning to visit Vermont for some time. I can see we need to add Woodstock to the plan when we finally do visit. Definitely fall would be a perfect time to visit. We love those old town main streets for unique finds.

Woodstock looks delightful. I haven’t been to Woodstock specifically, though we did have a leaf-peeping trip to Vermont a few years ago and absolutely loved it. I can see Woodstock would definitely be worth visiting with so many delicious local foods to sample and the wonderful artisan products to browse. That bowl is beautiful!

Vermont is one of the few US states I am really intrigued about. Would love to explore it someday. And Woodstock seems like a must-visit place when in Vermont!

Woodstock’s been on my short list of places to visit for quite a while and this post made me even more excited to visit!

The more I hear about Vermont, the more I want to visit. The colonial farm sounds like it’d be a cool place to stay!

Don’t forget to check out other stores in Woodstock like primrose, the unicorn and the VT flannel Co. Visit the reading greenhouse farm market in reading, VT, Great food at Chef Brad’s “crazy side” in Quechee. And check out OQ Farm in Woodstock for a possible family reunion place to stay. Other great eats… Claude’s, Casey’s caboose, in Killington (Claude’s is the BEST). And in Rutland don’t forget the Palms.

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15 things to do in woodstock, vt this spring, visiting woodstock in may, march in woodstock.

From The Blog 15 Things To Do in Woodstock, VT This Spring

The snow has melted, the birds are chirping and the first colorful flowers of spring are beginning to bloom in Woodstock, Vermont. Spring is in the air! It’s a rejuvenating time in our small town as the sleepy village begins to wake up, opening windows to take in the floral aroma of lilacs. Spring in Woodstock is a true delight with farmers markets, road races amongst scenic backdrops, sidewalk sales, parades, and this year, the first Pride event. Come have some fun this spring in Woodstock, VT. 

Check out our full calendar of events  here . 

Support Local Youth In The Race Around the Lake

Race Around the Lake is held in Barnard, Vermont, on May 19th just 20 minutes from the Woodstock Village. This stunning race loops around Silver Lake through trails in the state park. Runners can choose between a 10K run or a 5K run or walk. If you’re not around for the race this year there are virtual options as well. Participating in the race is a wonderful opportunity to support a local youth summer and theater program.

Head To The Trails For Mountain Biking

Woodstock, VT has some of the best trails in the state thanks to the Woodstock Mountain Bike Association (WAMBA). Trails are now open! Head to Mt Peg or Aqueduct Trails for great terrain from beginner to experienced. 

Watch The Memorial Day Parade

Woodstock’s Memorial Day Parade is a beautiful tribute to honor and mourn those who have served our country. Join us in commemoration on May 25th from 10:30-11am. Woodstock’s annual parade highlights the locals who have fought for our freedom. 

Dine Al Fresco

Longer days and warmer weather means plenty of opportunities for outdoor dining in Woodstock. Enjoy breakfast at  Mon Vert or  Soulfully Good Café on their outdoor patios. Get coffee at  Abracadabra and enjoy beautiful hillside views.  Au Comptoir is the place to be for outdoor cocktails. Sandwiches from  The Village Butcher or the Farmer’s Market make the perfect lunch on the go at Faulkner Park or The Green.  White Cottage is also open for the season so get some ice cream and enjoy it by the river.  

Support Your Favorite Village Shops At The Woodstock Sidewalk Sale

Walk Central and Elm Streets to enjoy outdoor shopping as the village shops open their doors May 24-25  during the Woodstock Sidewalk Sale . Take advantage of excellent sales at some of our favorite local shops. You can find a little something for everyone from beautiful clothing and local artisan made products to homeware and more.

Cheer On Runners At The Covered Bridges Half Marathon

People come from far and wide to run the  Covered Bridges Half Marathon as it is one of the most idyllic races in the country. This race actually sells out within minutes each year. The Half Marathon begins at Saskadena Six in Pomfret, Vermont on June 2nd at 8:15am and meanders through the Woodstock Village, along dirt roads parallel to the Ottauquechee River and ends in Quechee, Vermont. The CBM is always looking for  volunteers and cheerleaders . Find a place along the route to cheer on the runners. 

Join In The Festivities At The Inaugural Pride of Woodstock VT

Woodstock is proud to be hosting its first Pride event May 31-June 2.  Pride of Woodstock is a weekend long event in celebration of love, diversity and community. This Pride event combines the spirit of Woodstock, Vermont with the vibrant colors of the LGBTQ+ community, creating a unique and welcoming atmosphere for all.

The weekend of events begins on Thursday with a  movie at the Town Hall Theatre . Friday brings a  Welcome Reception at the Woodstock Inn and a  dance party at the Village Inn .

If running in high heels is more your cup of tea, join us for the  High Heel Race on Elm Street on Saturday, June 1 at 10:30am. Check out the  Pride of Woodstock event page for more happenings during the weekend including a  Drag Brunch ,  Tea Dances and  Gay Trivia at the Woodstock Inn & Resort.

Soar To New Heights At The Quechee Balloon Festival

The Quechee Balloon Festival , June 14-16, is a popular event and a great kick-off to summer. It is a miraculous sight to behold the colorful balloons scattered across the blue skies of the Upper Valley.  Grab tickets to enjoy the festival or  book a balloon ride to experience the magic from the air. The festival includes live music, crafts, yummy food and fun activities for the whole family to enjoy.

Watch The Woodstock Alumni Day Parade

The Woodstock Alumni Day Parade always falls the Saturday after graduation. It is a celebration of both the newest Woodstock Union High School graduates as well as all the classes prior. Alumni join forces to create fun themed floats and show their Woodstock pride. Come celebrate our alumni Saturday, June 15 at 2pm.

Enjoy Scenic Views On Woodstock Hiking Trails

Take a short stroll out of the Woodstock Village  to hike Mt. Peg . This beautiful trail is a short 1.3 mile loop that takes about 45 minutes to complete. At the top you will get sweeping views of Billings Farm and Killington. This hike is family-friendly and dogs are welcome on leash.

Mt. Tom is another favorite among locals and visitors for the gorgeously maintained trails and stunning scenery. You can begin the hike from Faulkner Park via the switchback trails, the National Park entrance, or Prosper Rd. for carriage trails. Some choose to hike to the Pogue to view the turtles sunbathing on logs and the pristine pond. If you continue beyond the Pogue you can make your way to the summit for epic views of the Woodstock village. This hike is family-friendly. Dogs are welcome on leash.

Attend the Bookstock Poetry Festival

Come witness Vermont’s largest poetry gathering in 2024 at the  Bookstock 2024 Poetry Festival June 21-22 at the North Chapel. Some of the country's most highly recognized poets will be in attendance.  See their website for the schedule of events and more information .

Treat Yourself To A Spa Day

The Spa at The Woodstock Inn & Resort is the perfect place for some rest and relaxation during your stay in Woodstock this spring. Pamper yourself with a day at the spa enjoying a massage, facial, manicure or pedicure. Be sure to enjoy the amenities including a eucalyptus steam room, sauna, whirl pool and outdoor pool once the weather warms up. 

Enjoy Music and Good Food at Feast and Field

A new season of  Feast and Field , marks the true beginning of summer in Vermont. Spending Thursday evenings amongst the scenic beauty of Fable Farm in Barnard, Vermont eating farm-fresh tacos and salads, Kiss the Cow Farm ice cream, local brews and wines and excellent live music is the absolute best way to do summer in Vermont. Head to Feast and Field every Thursday beginning May 30 through September for outdoor fun the whole family can enjoy.

Find Fresh Veggies, Flowers and Makers At The Market on the Green

The Market on the Green is Woodstock’s weekly outdoor market showcasing local artisan made products, food and beverages. Grab your fill of farm harvested veggies for the week, pick up your local flower CSA, buy artwork from local makers or get wood fired pizza and enjoy live music. The Market on the Green is a Woodstock tradition that brings out the entire community to congregate in support of our local small businesses. The Market on the Green runs every Wednesday from May 29 through October, 3-6pm.

See The Beauty Of Spring At Eshqua Bog Natural Area 

The Eshqua Bog Natural Area is a 41-acre protected space on Garvin Hill Rd. in Hartland, VT, located 10 minutes from the Woodstock Village. This beautiful botanical wonder features post glacial era bog and fern plants such as the lady slipper, larches and buckbean. May and June are popular times to visit the bog to see the showy Lady Slippers make their big debut. A boardwalk allows visitors to cross the bog and view the lady slippers up close.

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10 Perfect Things to Do in Woodstock VT in the Fall

By Author Tara Schatz

Posted on Published: April 4, 2024

There is no shortage of utterly charming villages in New England —  Norman Rockwell-esque towns that are beautiful in every season.

And in the fall, when nature’s colors give an extra boost to every red barn and covered bridge and add highlights to every tall-steepled church — well that, my friends, is why visitors flock to Woodstock, Vermont every year.  

Woodstock Village and the surrounding farms, mountains, and valleys are a leaf-peeper’s paradise.

As you ogle the blazing colors that surround you, why not sample incredible Vermont cheese, stroll across a covered bridge, visit Vermont’s only national park, walk through the treetops, and hike through the mountains?

No, you don’t need to wait until fall to visit Woodstock, VT — it’s gorgeous in every season!

Table of Contents

At-A-Glance: Woodstock, Vermont

Want to skip to the good part? Here’s a quick overview of everything you need to know to plan a weekend getaway to Woodstock, Vermont.

• When to Go:  Woodstock is undoubtedly one of the prettiest villages in the state, and visiting in the fall is a bucket-list trip for many!
• Where to Stay:   506 On the River Inn is comfy, clean, and just a short two miles from Woodstock Village.
• How to get here:  It’s about 85 miles from the Burlington International Airport (BTV), and it’s a beautiful, 1.5-hour drive.
• How to Get Around:  You’ll need a car to make the most of this rural area.
• Top 3 Highlights:   Marsh-Billings-Rockefeller National Historical Park , Billings Farm & Museum , hiking to the top of Mount Peg .

This is a local’s guide to the best things to do in Woodstock VT as well as the neighboring village of Quechee.

We’ve included our favorite tourist attractions, places to stay, and of course, our favorite hiking trails.

Planning a visit to Woodstock in the winter? Here’s an itinerary for a lovely winter getaway in Woodstock .

Ready to visit one of Vermont’s most lovely towns? Here we go.

The Best Things to Do in Woodstock VT in the Fall

Now that we’ve covered all the necessities, let’s get to the fun stuff. Here are the best things to do in Woodstock, Vermont in the fall, but of course many of these recommendations can be enjoyed year-round.

The small town of Quechee, Vermont is right next door to Woodstock, so we’re including some Quechee attractions here too.

Want a one-page printable itinerary for your perfect weekend in Woodstock? Here ya go!

Frolic with Farm Animals at Billings Farm and Museum

Farming roots run deep in Woodstock and the surrounding communities, and there’s no better way to experience life on the farm than at Billings Farm & Museum .

Located just outside the village of Woodstock, Billings Farm & Museum combines an award-winning Jersey dairy farm with one of the finest outdoor history museums in the country.

Not only can you meet more than 70 beautiful cows, but the farm is also home to goats, pigs, chickens, and five draft horses. 

Farm life exhibits are spread out across four historic barns and include displays featuring the seasonal activities that would have taken place on a Vermont hill farm more than 100 years ago.

The exhibits tell the story of rural life in Vermont at the turn of the century. What was it like to cut ice from the pond, shop at the general store down the road, or boil down maple sap into sweet syrup? 

After exploring the exhibits, be sure to stop at the Museum Store and Dairy Bar, where you can sample award-winning Billings Farm Cheddar and eat your fill of Vermont-made Wilcox ice cream. 

Finally, be sure to meander around the pastures, orchards, and Heirloom Garden.

Billings Farm & Museum is open every day from early – late October, from 10 am to 4 pm, and on weekends and holiday weeks, November 4th – February 25th, 10 am – 4 pm .

$19.00 : Adults ages 16-61 $16.00 : Seniors ages 62 and over $12.00 : Children ages -135 FREE:  Children under 3 and members

Explore the Gardens and Hike the Trails at Marsh-Billings-Rockefeller National Historic Park

Right across the street from Billings Farm & Museum is Vermont’s only national park unit — Marsh-Billings-Rockefeller National Historic Park (that’s a mouthful!).

Part nature preserve, part history museum, the National Park Service calls this unique park, “the only national park to tell the story of conservation history and the evolving nature of land stewardship in America.”  

The park is named for George Perkins Marsh, who developed an early philosophy of land stewardship that laid the foundation for the conservation movement in the United States between the 1830s and the 1860s.

Frederick Billings bought the estate in 1869 and established a progressive dairy farm on the property. His granddaughter, Mary French Rockefeller, and her husband, Laurance S. Rockefeller, continued to develop sustainable farming and forestry practices when they took over the property.

They established the Billings Farm & Museum in 1871 and donated the estate to the United States Government in 1992. 

During our recent visit, we were unable to tour the historic home, but there are miles and miles of trails that meander through the woods, past 400-year-old hemlocks, through pastures, and alongside rambling stone walls.

If you only have time to hike one trail, I’d recommend the Pogue/Mt. Tom loop, which is 4.2 miles and gains 643 feet in elevation.

I loved this hike so much that I added it to the 3rd edition of AMC’s Best Day Hikes in Vermont , which was released in May 2023.

Trails at Marsh-Billings-Rockefeller National Historical Park are free to access and are open every day from dawn to dusk. Use this Walk Woodstock trail map to explore all of the national park trails, as well as lots of others around Woodstock. 

The Carriage Barn Visitor Center at Marsh-Billings-Rockefeller-National Park is open from Memorial Day to October 31, from 10 am – 5 pm, and the grounds are open year-round.

The park is free to visit, but tours of the historic mansion will set you back $9 for adults, $5 for seniors, and $1 for children 15 and under. You can access the trails for free.

This unique national park unit is a must-visit and one of the best things to do in Vermont.

Stroll through the Treetops at Vermont Institute of Natural Science (VINS) in Quechee

There are many reasons to visit the Vermont Institute of Natural Science in Quechee, Vermont — raptors, reptiles, and trails, but the coolest new feature is a forest canopy walk that lets you stroll through the treetops.

The boardwalk is ADA-accessible and brings visitors 65 feet above the Ottauquechee River — eye-to-eye with the songbirds and squirrels that make their home in the forest. 

The attached treehouse brings visitors even higher into the canopy with a 360-degree view of the surrounding countryside. You’ll also find a giant, climbable spider web with three layers of netting and an open weave to see down to the forest floor. 

VINS is open every day from 10 am-5 pm.

Adults: $19.50 Youth (4-17): $16.50 (Must be accompanied by an adult) VINS Members and children 3 and under: Free

Unfortunately, pets are not permitted.  Visit VINS to learn more.

Sample Mouth-Watering Cheeses at Sugarbush Farm in Woodstock

Looking for any excuse to sample some incredible Vermont cheeses? Me too!

Not only is Sugarbush Farm in Woodstock one of the prettiest farms we’ve ever been to, but it’s also the maker of award-winning cheddar cheese and delightful maple syrup.

If you’re a foodie, a stop here is one of the best things to do in Woodstock VT.

Bring your camera and a picnic and plan on spending a few hours at Sugarbush Farm, which encompasses 550 acres. Be sure to visit the sugar house, the cheese packing room, and the farm store. Chat with the cows, meander in the woods, and enjoy this little piece of Vermont heaven. 

Sugarbush Farm is free to visit and is open every day except Thanksgiving and Christmas from 8 am-5 pm during the week and from 9 am-5 pm on weekends and holidays.

For directions or to visit the online store, check out Sugarbush Farm . 

Hike the Quechee Gorge Trail along the Ottauquechee River in Quechee

Quechee Gorge is known as “Vermont’s Little Grand Canyon” and at 165 feet, is the deepest gorge in Vermont.

Because Quechee Gorge can be easily viewed from the Route 4 bridge, it is also one of the most popular tourist spots in Vermont, attracting more than 200,000 visitors annually. 

The gorge is certainly beautiful, and worth stopping for a photo, but if you visit in the fall, be prepared for throngs of people starting around 10 am and lasting well into the evening.

In addition to viewing Quechee Gorge from the bridge, I recommend hiking the Quechee Gorge Trail , which isn’t quite as crowded as the bridge location.

The trail is 2.7 miles (round trip) and gains 200 feet in elevation.

If you have time, park your car at the Quechee Visitor Center and walk across the street to Dewey’s Pond. This is a nice, level path that goes past the dam and out to a pond full of geese.

The colors are lovely on a fall afternoon. 

When you get to the small parking area, turn around, retrace your steps, and then head down into the gorge. If you are short on time, skip Dewey’s Pond and just hike down to the gorge.

Quechee Gorge Trail descends through a forest of hemlock and mixed hardwoods, which are so pretty in the fall.

There is a chain-link fence along the gorge to keep people from falling, but once you are down at river level, you can walk out onto the rocks along the river, and even go swimming if it’s not too cold. 

There’s a little snack bar across from the gorge that serves ice cream, burgers, and fries — perfect for a post-hike snack. 

If you don’t mind roughing it, Quechee Gorge State Park is a great spot to pitch your tent or park your RV. This is an affordable way to explore the best things to do in Woodstock, VT.

Finally, if you’re planning a summer trip to the Woodstock area, you might want to time your vacation to coincide with the wonderful Quechee Balloon Festival . The 2024 festival takes place from June 14-16, and is one of the best annual festivals in Vermont .

Visit a Covered Bridge or Two (or Six)

There are more covered bridges per square mile in Vermont than in any other state — more than 100!

The Woodstock area has several beautiful covered bridges that are worth exploring. All of these covered bridges are within a 10-mile drive of Woodstock. Don’t forget your camera!

Middle Covered Bridge : Located right in downtown Woodstock on Mountain Avenue, Middle Covered Bridge spans the Ottauquechee River and was constructed in 1969 using traditional materials and methods, including wooden pegs instead of nails.

This lattice truss bridge is 139 feet across and is probably the most photographed bridge in the area. Park your car in Woodstock Village and walk across Middle Covered Bridge on foot. 

Taftsville Covered Bridge : Located east of Woodstock on Route 4, the Taftsville Covered Bridge is bright red and one of the oldest covered bridges in the nation (1836).

At 189 feet, it is the second-longest covered bridge in Vermont. This was my favorite bridge to photograph during our recent visit. 

Quechee Covered Bridge : The sweeping views from the Quechee Covered Bridge are pretty phenomenal in every season.

Located near the famous Simon Pearce Glassware store and restaurant, this beautiful bridge had to be rebuilt in 2012 after Hurricane Irene caused significant damage the year before. There is a small park and easy parking nearby.

Willard Covered Bridges : Located in North Hartland, Vermont (about 13 miles from Woodstock), these two bridges are connected by an island in the Ottauquechee River.

The western bridge was built in 2001. The eastern bridge was built in 1870 and is listed on the National Register of Historic Places. You can take an easy trail down below the dam to get some great photos of the bridges and the river. 

Lincoln Covered Bridge : The Lincoln Covered Bridge is located on Route 4 in West Woodstock. It was built in 1877, and at the time it was the only known example of a Pratt truss design, featuring flanking arch trusses made of six laminated layers. 

Check out Simon Pearce for the View, the Food, or the Amazing Glassware

Simon Pearce Glassware has been handcrafted in Quechee, Vermont since 1981.

This beautiful spot on the Ottauquechee River (near the Quechee Covered Bridge) is powered by hydroelectricity and features the Simon Pearce flagship store and glass-blowing demonstration facility, showroom, and restaurant. 

Glass-blowing demonstrations are offered daily, and the restaurant is open for both lunch and dinner.

Simon Pearce was also voted one of “America’s Most Romantic Restaurants” by Travel and Leisure Magazine.

During our recent visit, had a light lunch, which was divine — Vermont cheddar soup and fresh greens, plus a sparkling wine and chocolate mousse for dessert!

The food and the view competed for our attention the whole time. Incredible.

Step Back in Time in Woodstock Village

With a nice collection of historic buildings surrounding a central town green, a thoroughly walkable downtown, and picture-postcard scenes around every corner, is it any wonder that Woodstock has been named one of the most beautiful small towns in America over and over again? 

From Woodstock Village, you can easily access Billings Farm and Museum, Marsh-Billings-Rockefeller National Historic Park, and Middle Covered Bridge. It’s one of the most walkable communities we’ve stayed in!

If you are a fan of historic architecture, be sure to spend time wandering around admiring the restored Georgian, Federal Style, and Greek Revival homes.

The best way to explore Woodstock Village is to park your car downtown and simply explore.

On Wednesdays, be sure to check out the Market on the Green, which takes place on the Village Green from 3-6 pm between June and mid-October.

Shop ‘Til You Drop?

Because I spend most of my discretionary dollars on traveling, I rarely have money left over for shopping. I do, however, love exploring some of the small, local shops in Woodstock and Quechee on a rainy day. 

In Woodstock, check out F.H. Gillingham & Sons , an old-fashioned country store that has been in operation since 1886. You’ll find a little bit of everything inside, from hardware and sporting goods to local cheese, toys, and fishing supplies.

Some of our other favorites in Woodstock include the Clover Gift Shop , the Yankee Bookshop (I can’t resist a bookstore!), and Vermont Eclectic Company , Woodstock’s newest (and super unique) gift shop. 

In Quechee, I recommend stopping at the Vermont Antique Mall , which is full to bursting with cool treasures, whether you’re into pottery, textiles, furniture, or old tools.

The Vermont Antique Mall has 17,000 square feet of treasures, so be prepared to spend some time exploring. It’s open from 10 am to 5 pm every day except Easter, Thanksgiving, Christmas, and New Year’s Day. 

Have a Picnic on Top of Mount Peg

If you wake to a beautiful morning and just have to spend the day outdoors, grab some picnic food at Jake’s Quechee Market and hike the short trail to the top of Mount Peg , one of the most beautiful trails in Woodstock.

The trail begins in a residential area (parking for about three cars) and climbs through woods and fields to the summit of Mount Peg. It’s not a hard hike, and there are benches and a picnic table at the top. 

The views of Woodstock are fabulous, especially for such a short climb!

Bring your camera and plan to spend some time at the top. When you’re ready to return to your car, take the Spruce Trail, which will lead you back into the woods and down the mountain.

This was one of my favorite hikes of our weekend in Woodstock. I hiked up with my coffee and breakfast and it was so peaceful and beautiful!

Where to Eat in Woodstock and Quechee

Need some suggestions for awesome eats in Woodstock, Vermont? Sampling all the local food options is one of our favorite pastimes. Here are our recommendations for dining in Woodstock.

Note: A food photographer I am not. You’ll have to check out these eateries based on my recommendations and not my sub-par photography, which I won’t include here.

Best place for ice cream in Woodstock: Woodstock Scoops is a farm-to-cone establishment that will entice you to go above and beyond your favorite flavor. There’s also a good chance that you’ll find yourself here every single afternoon.

Best farm-fresh groceries: Jake’s Quechee Market has everything you need — local craft beer, farm-fresh meats and veggies, prepared foods, and even Vermont gifts. The location is great too! We also love Woodstock Farmers Market .

Best breakfast in Quechee: The Skinny Pancake , right next to Jake’s Quechee Market on Route 4 in Quechee. The best crepes in Vermont. And real maple syrup, of course!

Best breakfast in Woodstock: For awesome coffee and locally sourced food in a cool, relaxing space, pop into Mon Vert Cafe in Woodstock. Their breakfast burrito is so filling and so yummy!

Best fine dining: Simon Pearce in Quechee. It’s worth it for the views alone, but the dinner and lunch entrees are uniquely prepared, beautiful, and delicious. We also love the Prince & the Pauper in Woodstock.

Best casual fare: Worthy Kitchen in Woodstock serves comfort foods like burgers, mac-and-cheese, and chicken wings, plus some delectable vegetarian options. The fries are a favorite treat!

Woodstock, VT Hotels and Vacation Rentals

There are a lot of unique accommodations in Woodstock and Quechee!

Depending on when you book your hotel reservations, you may have to choose entirely based on what’s available, especially if you wait until the last minute. Make your reservations as early as you can to ensure you have choices.

Here are our top picks for places to stay in Woodstock and Quechee.

Woodstock Inn & Resort : This posh resort is located in Woodstock Village, within walking distance of everything downtown. It’s the perfect spot for a special weekend, or fall getaway when you can take advantage of all the best things to do in Woodstock VT.

506 On the River Inn: Rooms with panoramic river and garden views steal the show, and 506 On the River Inn features an indoor pool and sauna, a gym, game rooms, and a restaurant.

Log Cabin Apartment in Woodstock: Walk to everything from this beautiful apartment with room for four guests. This special spot is located in a wooded setting but is just a 1/4-mile to downtown. There’s a full kitchen if you don’t want to dine out in Woodstock.

Historic Cottage on a Vineyard: A beautiful, 900-square-foot cottage on Gilbert’s Hill with access to hiking trails. The space includes two bedrooms, one bathroom, a full kitchen, and a private deck overlooking the vineyard.

Historic Library in Quechee: We love this historic library in Quechee, which you can find on Airbnb. It’s small, so perfect for a romantic getaway for 2, plus it’s dog-friendly!

Read Next: Spend a Winter Weekend in Woodstock, Vermont

A Complete Itinerary for a Weekend in Woodstock, VT

Not sure how to structure your days? If you’re visiting Woodstock and Quechee for a summer or fall weekend, here’s what we’d recommend. You can get a printable itinerary by signing up for our email list below.

Friday Afternoon: Arrive and Explore Quechee

• Drive to Quechee, Vermont
• Hike the Quechee Gorge Trail and take in the views from the Route 4 bridge
• Check into your hotel or vacation rental.
• Drive into downtown Quechee and park near the Quechee Covered Bridge
• Dinner at Simon Pearce Restaurant

Saturday: Woodstock Historic Sites

• Rise and shine. Head over to the Skinny Pancake for Breakfast
• Visit Marsh-Billings-Rockefeller National Historic Park . Tour the house and gardens, and hike the Pogue/Mt. Tom loop
• Lunch at Mont Vert Cafe in downtown Woodstock
• Spend some time walking around Woodstock Village
• Walk to Billings Farm and Museum to meet the animals, sample cheeses, and learn about farm life
• Dinner at Worthy Kitchen in Woodstock

Sunday: Hiking and Shopping

• Pick up a picnic breakfast at Jake’s Quechee Market or Woodstock Farmers’ Market (depending on where you’re staying)
• Hike to the top of Mount Peg in Woodstock for a picnic
• Woodstock Village for some shopping and exploring
• Lunch at Soulfully Good Cafe followed by ice cream at Woodstock Scoops.
• Stop at the Taftsville Covered Bridge between Woodstock and Quechee
• Visit the Vermont Antique Mall in Quechee

FAQs for Visiting Woodstock VT

Now that you know the best things to do in Woodstock VT, let’s talk details and logistics.

Here are a few crucial pieces of information to help you plan your trip to Woodstock and Quechee.

When is the Best Time of Year to Visit Woodstock, Vermont?

We have explored Woodstock and Quechee in every season, and I’m going to vote for October. The fall foliage season is EPIC, full stop. If you haven’t experienced a Vermont fall, it’s time to make amends. 

Fall foliage in Woodstock, Vermont doesn’t happen like clockwork from year to year, but you can expect great colors from early October until about the third week of the month, give or take a few days. 

If you are planning a fall trip to Woodstock, starting early is crucial!

Woodstock in the fall is popular and crowded. Reserve your Woodstock lodging six months in advance for the best selection, and if you want to avoid crowds during your visit, plan to visit during the early part of the week.

Woodstock in the summer is full of outdoor eateries, farm stands, and swimming holes. It’s our 2nd favorite time to visit.

In the winter, you can hop on a horse-drawn sleigh, sip mulled cider as the snow falls gently past your window, and take some serious adventures on snowshoes and cross-country skis. The trails around Woodstock are a snow lover’s paradise!

Also Read: The 95+ Best Things to Do in Vermont

How to get to Woodstock, Vermont

Half the fun of a Woodstock, Vermont vacation is the road trip to get there.

The closest major airport is Burlington International Airport (BTV), which is 86 miles away. From there, you can rent a car , and embark on the New England road trip you’ve been dreaming about. 

 The capital city of Montpelier is a fun day trip from Woodstock, with its gilded dome that sits atop one of the oldest and best-preserved state capitols in the nation. It’s about halfway between Burlington and Woodstock.

The drive from Burlington to Woodstock is less than two hours, whether you choose to lodge in Woodstock or nearby Quechee. 

How Long Should You Stay in Woodstock, Vermont?

You can cram lots of fun into a single weekend in Woodstock, but I think four days is the sweet spot.

Plan on a day in Quechee and a few in Woodstock. The towns are right next to each other, so you can drive back and forth between the two very easily.

If you are into shopping and/or antiquing, you can easily spend a full day exploring all the shops in Woodstock and the Antique Mall in Quechee, so plan accordingly. 

Read Next: The Best Places to Visit in Vermont in the Fall

Packing Tips for a Fall Weekend in Woodstock, Vermont

Vermont is delightful in that it embraces all four seasons with glee — sometimes all in the same week!

Because many of our recommendations involve getting outside and enjoying the crisp fall air, frolicking with farm animals, and crunching leaves under your boots, I thought I’d share some of our favorite apparel and gear for getting outside in the fall. 

• Wool layers – Merino wool is a magical fabric. You can wear it for days without having to wash it (no funk!), it wicks away sweat, keeps you cool in the summer and warm in the winter, and dries incredibly fast. We get our favorite merino wool clothing from Woolly Clothing Co. , which has the softest wool layers for both men and women.
• Hiking pants that don’t look like hiking pants – Yes, you’ll be spending a lot of time outdoors, but you want pants that can take you from trail to tavern without looking frumpy. During my recent trip, I wore these Halle Hiking Pants from Prana , which come in lots of colors and short sizes with a 30” inseam. They were perfect for my fall weekend. 
• A chunky scarf or two
• Wool socks – Warm toes are happy toes! I recommend getting a couple of pairs of wool socks from Darm Tough Vermont . They’re made in Vermont and unconditionally guaranteed for life. 
• Hiking shoes – Sturdy footwear is a must for your trip to Woodstock. If you haven’t found your perfect pair of hiking shoes, now is the time to get fitted at your local shoe store. 
• A thermos – You can’t have fall adventures without a thermos of something warm and delicious in your backpack, whether it’s a hot cider or hot soup. This unbreakable thermal bottle from Stanley gets the job done and easily fits in a purse or backpack. 

Psst… Looking for a printable itinerary for visiting Woodstock, Vermont in the summer and fall? This weekend itinerary includes our favorite hiking trails, historic sites, and restaurants, plus ideas for where to stay in Woodstock. Sign up for your free copy!

Follow us on social media for more Vermont inspiration!

Tara Schatz is a freelance writer and the founder and editor-in-chief of Vermont Explored and Back Road Ramblers , an American road trip blog. She is also the co-author of the 3rd edition of AMC’s Best Day Hikes in Vermont, released in May 2023, and the author of 100+ Wonderful Ways to Experience Vermont.

Saturday 15th of October 2022

I've spent a lot of time exploring Vermont, and this is one of the best articles I've read. Thanks.

Sunday 7th of November 2021

We typically visit Woodstock on a yearly basis. In the past we have always lodged at 506 on the River. Their laid back but high end accommodations along with their excellent food, awesome bar and pool/games room makes for an enjoyable stay. Simon Pearce is a must see for their food and glassware. We love to go to Long Trail brewery for beer and charcuterie board. The people of Woodstock are always welcoming. The little shops are super fun! Suicide Six is probably my favorite low key ski mountain. Sugarbush is an adventure in itself just getting there, especially if there's snow on the ground, but definitely worth the trip.

Thursday 11th of November 2021

@Darcey, I just read your very helpful review & have plans to spend this weekend at 506 On the River! I’ve been to Simon Pearce but never dined there. I have never stayed in the Woodstock/Quechee area & I'm excited to see the sights!

Loren Spencer

Saturday 24th of July 2021

I want to relocate to Vermont so bad!

Friday 10th of September 2021

@Loren Spencer, same here! It seems amazing! We are really hoping to in a few years. I'm from the Ozarks originally and a lot of these pictures remind me of the autumns there.

Robbie Brown

Tuesday 9th of March 2021

Sugar Bush farm is the best. I have been there twice & will visit again. This California gal loves Vermont

Woodstock Vermont in Fall | Best Spots + 10 Things to do in Woodstock VT in Fall

August 31, 2022

Anna Hammerschmidt

With crisp temperatures, the crunch of leaves underfoot, and outstanding autumnal decor, meandering through the quaint town of Woodstock, Vermont, will likely be a highlight of your Fall trip to Vermont . Seeing Woodstock, Vermont, in Fall is an incredible experience. It has everything you could want from a festive Fall getaway in New England. 

The town of Woodstock comes to life with vibrant Fall foliage , and many of the residents even go the extra mile to decorate their homes elegantly with pumpkins and mums. When you’re not strolling through town, you’ll be seeking out the best Fall foliage, farm hopping, and indulging in maple creemees .

This is such a cute town that you will be planning your next trip back after one Fall getaway to Woodstock, VT.

Disclaimer: This article contains affiliate links. I may earn a small commission when you purchase a product or book a stay through these links at no extra cost to you.

Table of Contents

Woodstock Vermont Fall Foliage- When is Peak Fall Foliage in Woodstock, VT?

Peak fall foliage in Woodstock typically lands from the last week of September to early October. However, it can vary depending on the year. The Vermont Foliage Forecaster is an excellent tool to estimate when you’ll find the best colors in Stowe.

If you plan on visiting the second or third week of October, you should see some great foliage. Looking at the peak for the prior year can usually help you determine the best time to visit.

Things to do in Woodstock, Vermont in Fall

This list of best things to do in Woodstock, VT in Fall includes the best spots to see Fall foliage and festival Fall activities. Many of these activities can be done year-round, yet they are especially worthwhile when visiting Woodstock in the Fall. This list also includes some things to do in Quechee, Vermont in Fall . The town is nearby Woodstock and is easy to include during your trip to Woodstock.

Explore the Town of Woodstock

The town of Woodstock is so charming. During the Fall months, many Inns, shops, and houses in Woodstock are decorated with autumnal decor. You’ll find cute pumpkin displays around town and stunning Fall foliage that make the Woodstock, Vermont village even more picturesque.

With so many trees lining the roads in Woodstock, the entire town is perfect for a leaf-peeping stroll. If you want to see the best Fall photo spots in Woodstock, those are highlighted later in this guide.

Get Maple Syrup at Sugarbush Farm

Sugarbush Farm is a maple farm near Woodstock and is a great spot to visit in the Fall. What better way to spend some time in Vermont in Fall than a scenic drive to a farm selling maple syrup cheese? I’m not quite sure if anything could be more Vermont than that. 

Before browsing the shop, don’t miss the maple syrup and cheese samples. Sampling will help you decide which bottle of syrup to bring home! At Sugarbush Farm, you can take a self-guided tour through the maple house and stroll through the maple trees to a quaint chapel in the woods.

READ MORE: Visiting Sugarbush Farm in Woodstock VT

Take Photos of Sleepy Hollow Farm

Sleepy Hollow Farm is a picturesque farm outside of Woodstock. During the Fall, tourists and photographers flock to this farm to see the stunning Fall foliage. From the road, this farm is stunning, with its long driveway and vibrant trees in the background. Stopping at Sleepy Hollow Farm is one of the top things to do in Woodstock, VT, in the Fall.

Keep in mind that this is a residential farm. Keep off their property. You can get a gorgeous photo from the road, so there is no need to violate their privacy.

Get a Maple Creemee at Woodstock Scoops

While on a Fall trip to Woodstock, Vermont, you must indulge in a Maple Creemee. A maple creemee is maple-flavored soft-served ice cream (Vermonters call soft-served ice cream creemees, which is the cutest thing in the world). Woodstock Scoops is the best spot to grab one of these Vermont treats. This ice cream shop is located in the village of Woodstock and is a great spot to stop for a treat while walking around.

Visit Billings Farm & Museum

Billings Farm is a working farm and outdoor museum that is a fun place to visit on a Fall trip to Woodstock. Visiting Billings Farm & Museum gives you an idea of what life is like on a farm in the Fall months in Vermont. 

While at Billings Farm, you will have the opportunity to see a fully-operational Jersey dairy farm, see animals and see demonstrations of cheese making. They even have apple cider donuts available in the Fall.

Price: $17 for adults, $8 for kids (4-15), and Free for kids 3 and under Address : 69 Old River Rd, Woodstock, VT 05091

Visit the Covered Bridges

Visiting the bridges in Woodstock is such a fun thing to do during your Fall trip. There are more than 100 covered bridges in Vermont, so it is no surprise that visiting these bridges is popular in the state. These bridges are often in scenic locations, which makes them even more picturesque with Fall Foliage. Some of the top bridges to see in Woodstock are Lincoln Covered Bridge, Middle Covered Bridge, Taftsville Covered Bridge, and Quechee Covered Bridge .

Walk Along the Treetops

There is a forest canopy walk at The Vermont Institute of Natural Science in Quechee. This canopy walk allows you to walk along the treetops and is a unique way to experience the stunning Fall foliage. Vermont has some of the best Fall foliage in the world, and this is truly one of the best ways to experience it.

The Vermont Institute of Natural Science is an underrated spot that it seems not many people know about. I was surprised that there weren’t many people at the forest canopy walk, especially during peak foliage. Be sure to add this to your list of places you must visit if you are visiting Woodstock, Vermont, in the Fall.

Price: $18 for adults, $15 for kids (4-17), and Free for kids 3 and under Address : 149 Natures Wy, Quechee, VT 05059

Shop at Woodstock Farmers Market

The Woodstock Farmers Market is a great spot for local Vermont goods year-round. And in the Fall months, you can pick up fun-festive things such as Maple-syrup, mums, and pumpkins. This was a great spot to stop for a quick bit to eat to bring on scenic Fall drives near Woodstock. P.S. Woodstock Farmers Market has the most adorable Fall-themed sugar cookies that are delicious.

Hike the Quechee Gorge

Quechee Gorge is one of the most scenic spots to see Fall foliage near Woodstock, Vermont. This gorge, known as “Vermont’s Little Grand Canyon,” is located in the neighboring town of Quechee and offers a scenic and easy hiking trail. You can hike the 2.7-miles trail that follows the gorge or view the gorge from above via the bridge.

Get a Maple Latte at Mon Vert Cafe

A trip to Vermont should include indulging in maple-flavored everything, including coffee. Perhaps it is just the coffee-lover in me, but I think a maple latte is a daily staple on a Fall trip to Vermont. And Mon Vert Cafe in Woodstock is the perfect place for your maple-flavored caffeine fix. Mon Vert Cafe has a wide array of beverages and pastries and is the ideal spot to start your day.

Fall Photo Spots in Woodstock, Vermont

In the last section, I mentioned how charming the village of Woodstock is. In this section, we will dive into where to find the best autumnal decor and Fall photo spots in the town of Woodstock, Vermont .

Woodstock Inn

Woodstock Inn is a quintessential New England Inn and is incredibly charming in the Fall. The inn is beautifully decorated with pumpkins and dozens of mums near the entry. The flowers frame Woodstock Inn and create a great spot to take Fall photos in Woodstock.

Woodstock Inn is one of the most popular photo spots in Woodstock. Chances are, you will not be the only person trying to take photos here. Try to arrive early to get pictures before it gets too busy, and have patience if you need to wait for others to finish taking their pictures.

The Ardmore Inn

The Ardmore is another charming inn located in Woodstock, Vermont. This Inn does a cute autumnal display facing Pleasent Street at the property’s entrance. There are mums in shades of orange lining the walkway and piles of pumpkins on the steps. It is really cute.

All information I found online says that the Ardmore Inn has been closed for the last two years. However, even though there was no booking information online, the inn was still decorated last year.

General Lyman Mower House

This historic home was built on the site of the first county courthouse in Woodstock, Vermont. Architecturally, it is stunning. And a vibrant red tree is in front of the property, making a lovely photo opportunity in the Fall.

There is a small park across the street from this house. You’ll want to take photos from across the street to get the house and tree in your photo completely.  

587 Old River Road

This section of Old River Road is gorgeous, with white fencing and orange and gold-hued foliage. It’s a great spot to allow the foliage to shine in photos, rather than the albeit adorable town of Woodstock. 

The property spans a large portion of Old River Road, so there are plenty of spots to choose from to take photos of. Just look for a space with the most leaves still on the branches.

Middle Covered Bridge

Middle Covered Bridge is located within the village of Woodstock and is a very “Vermont” photo op. Seriously, you cannot visit Vermont without seeing at least one covered bridge (or a dozen). 

You have to get a little creative with the angle you shoot from to showcase some of the surrounding foliage, but the photos will surely turn out really cute.

11 the Green

This house is located next to Middle Covered Bridge and is so charming. The house is decorated with pumpkins lining the walkway, and various trees behind the home make it extremely picturesque. 

16 Pleasant Street

This white house with a white picket fence is a simple yet stunning spot to take Fall photos in Woodstock, VT. The owner of this residential property places tinny pumpkins on all the fence stakes. 

If you take a photo from an angle, you can see all the little pumpkins lining the fence.

The Laundry Room

Yes, The Laundry Room is, in fact, a laundromat. And it is the cutest laundromat ever. The Laundry Room, located on Pleasant Street, has fantastic decor in the Fall. The display includes vibrant orange pumpkins, Fall wreaths, and flowers. 

First Impressions Salon & Spa

The red brick exterior of this salon is the perfect backdrop for the seasonal Fall decor. The front steps have a cute autumnal display and are a great spot to take Fall photos in Woodstock, Vermont.

Where to Stay in Woodstock, VT in Fall

Here are a few of my top recommendations for where to stay in Woodstock, Vermont . Remember that accommodations are likely to sell out during October. If you are already planning your trip, that means everyone is starting to plan their trips. Book ASAP to ensure you have a good place to stay.

Woodstock Inn & Resort

The Woodstock Inn & Resort is the most iconic place to stay in Woodstock. This inn exudes quaint New England luxury. The rooms are spacious and elegant, and the location is prime. Staying at Woodstock Inn is a bit of a splurge, but it is worth every penny if it is within your budget.

The Vesper Woodstock is a modern bed and breakfast located just in the town of Woodstock. This property is very small and offers a limited number of rooms. Book fast if you want to secure a room here.

The Shire Woodstock

The Shire Woodstock is situated along the Ottauquechee River and offers beautiful river views from the rooms. While the scenic views make this property feel a bit more secluded, it is still within a few minutes walk to the center of town.

Fall in Woodstock, Vermont: Wrap-up

Woodstock is one of the best places to experience Fall in Vermont. There is so much to do in Woodstock, especially during the Fall season; whether you are meandering the town of Woodstock for seasonal decor or checking out some of the best things to do in the area, you will surely have an incredible time with a Fall getaway to Woodstock. Woodstock is the type of town that will pull at your heartstrings and beckon you to plan a return trip after your first visit. 

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How to Spend 24 Scenic Hours Around Woodstock, Vermont

Eat well while enjoying the fall color in Quechee, Bridgewater, Plymouth, and Woodstock, VT

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Share All sharing options for: How to Spend 24 Scenic Hours Around Woodstock, Vermont

Woodstock, Vermont, just about three hours by car from Boston, is a quintessential New England getaway, especially for autumn leaf-peeping. Together with its surrounding towns of Quechee, Bridgewater, and Plymouth, this area ticks all the Vermont-core boxes: fall foliage, covered bridges, and craft beer and spirits. Grab your hiking boots and camera and prepare to sip maple-infused cocktails and sample cheddar based on a recipe from late President Calvin Coolidge’s dad.

8 a.m. breakfast at Soulfully Good Cafe

Start your day at Soulfully Good Cafe, inside a pink house with white picket fence that encloses a cute patio dotted with umbrellas — weather-permitting, it’s people-watching paradise. The thoughtfully decorated interior makes you feel right at home with its loungy couches and full bookshelves. Load up on breakfast fare such as avocado toast and omelets, or grab a fruit parfait to go.

Activity interlude: Stroll through town

From breakfast, stroll southeast along pedestrian-friendly Central Street, lined with shops selling flannel, books, gifts, and art — in particular, Collective is a lovely cooperative showing off many artists’ works. A short detour north onto Elm Street leads to more gems like Village Butcher Shop , whose sandwiches are superb fuel for later activities, and family-owned general store F.H. Gillingham & Sons , selling the likes of pickles and penny candy here since 1886. Back down Central Street, you’ll soon enter the heart of Woodstock — the town Green, ringed by historic buildings like the public library from 1883 — and spot the Middle Covered Bridge over the Ottauquechee River. This bridge is a relatively new replacement from 1969; worthy of a postcard, it stretches nearly 140 feet across the river, protected from snowy winters by a sturdy roof.

9:30 a.m. coffee at Abracadabra Coffee Co.

Before you tackle any major outdoor activities, make sure to stop by Abracadabra Coffee Co., which takes the surprising form of a vintage white Shasta camper nestled inside a barn off Route 4. The selection of single-origin coffees takes you on a journey to the coffee belt, from Peru to Costa Rica, and little snacks like Liège waffles and caneles make perfect companions.

Activity interlude: Hike the Pogue and Mt. Tom trail

About a half-mile walk north of the town center is the entrance to Marsh-Billings-Rockefeller National Historical Park , where you can hike the 4.2-mile Pogue and Mt. Tom loop that immerses you in the sights and sounds of fall. The Pogue, a scenic little pond sandwiched between the nearby mountains, is a good place to stop for a snack. If you’re up for an easier and shorter route, you can go around the Pogue via Prosper Road, which is about 2.5 miles and takes about one hour to complete. You can also combine this activity with a visit to the nearby Billings Farm and Museum , a historic working dairy farm with a sunflower labyrinth, seasonal exhibits, Jersey cows and draft horses, and cheese made on-site.

12 p.m. lunch at Mon Vert Cafe

After the hike, refuel at Mon Vert Cafe back on Central Street. Owner Samantha DiNatale purchased the cafe from previous owners in 2015 and has since expanded the chalet-style house into a 3,100-square-foot space with two floors of seating plus a patio. Be sure to order the Monte Vert Cristo, a savory challah French toast sandwich with pan-fried ham and melty Cabot cheese that comes with a side of real maple syrup. Just as importantly, the menu has an extensive vegan and vegetarian selection that ranges from breakfast burritos to mushroom sandwiches, with fresh bread from Vermont’s Red Hen Baking.

Activity interlude: Shop the Quechee Gorge Village

About a 15-minute drive east, in Quechee, you’ll find this charming collection of attractions and stores. Wax nostalgic over Pez dispensers and Star Wars lightsabers at the Toy Museum, then unearth vintage toys among the fine china and art sold by hundreds of vendors at the Vermont Antique Mall — or pick up modern ones at Vermont Toys and Games . Stock up on Vermont-made souvenirs like cheese, wine, and maple syrup at the Quechee General Store , and get the farm-to-closet experience at Vermont Alpaca Store , which sells scarves and sweaters made from the wool of the adorable rescue alpacas outside. If you get thirsty, sample gins made with wild Vermont juniper berries and vodka distilled entirely from local maple syrup at Vermont Spirits Distilling Co.

Alternative activity interlude: Hike the Quechee Gorge

If you prefer to stretch your legs some more, this is the deepest gorge in the state, affectionately dubbed “Vermont’s Little Grand Canyon.” You can appreciate it from the Quechee Gorge Bridge spanning the Ottauquechee River, or get a closer look on a short, easy hike of about 1.3 miles.

4:30 p.m. visit to Whistlepig Whiskey Parlour

Part of Quechee’s historic Parker House has been transformed into a tasting room for Whistlepig , distillers of some of the country’s finest rye whiskey. The second-floor tasting room is all inviting leather sofas and dim lighting, with antique picture frames telling the history of the house. Some rarities are available only on the premises, such as the 18-year double malt rye aged in virgin oak barrels, and a 12-year cask rye aged in a combination of oak, Madeira, sauternes, and port barrels. Note that it’s free to visit but you have to reserve a 30-minute appointment in advance.

Alternative: Beer at Long Trail Brewing Co.

A 15-minute drive west of Woodstock, grab a beer at this brewpub right on the Ottauquechee River. Though most New Englanders can pick up the long-standing brewery’s famous Long Trail Ale at their local liquor store, the taproom always offers something special, including limited-edition brews like a barrel-aged version of Triple Bag, a whopper at 11 percent ABV. While you’re out this way, don’t miss the President Calvin Coolidge Historic Site , a museum at the birthplace of the 30th president of the United States, and Plymouth Artisan Cheese , which uses the same building and cheddar recipe from 1890 that Coolidge’s father did.

5 p.m. glassblowing and dinner at Simon Pearce

U.S. presidents have been known to give Simon Pearce’s high-quality glassware to foreign dignitaries, and the company’s flagship store and restaurant in Quechee is an adventure unto itself. It occupies a historic mill overlooking a picturesque dam, Mill Pond Falls, and the Quechee Covered Bridge, and most days if you come early for a 6 p.m. dinner reservation you can watch glassblowers at work, shop the allegedly imperfect seconds, and then have a creative cocktail at the bar. The restaurant’s atmosphere is simply grand, with floor-to-ceiling windows, brick walls, and polished wooden floors. Much of its menu rotates seasonally, possibly including horseradish-crusted cod or vegetable pappardelle with wild mushrooms, though some signatures like a creamy Vermont cheddar soup remain constant.

Ideas for dinner in Woodstock include Cambodian and Thai at Angkor Wat ; classic American at the Red Rooster ; and Modern French and American at the Prince and the Pauper .

9 p.m. cocktails at Au Comptoir

Back in Woodstock, this relatively new cocktail bar has a patio and stays open later than most competitors — although only till 10 p.m. (Sorry, night owls.) Spirits made by nearby Mad River Distillers are a mainstay on the cool yet cozy bar’s eclectic menu, from a sidecar based on apple brandy to a barrel-aged Negroni incorporating maple-cask rum. Seasonal mocktails hit the spot as well. Not a cocktail person? Interesting wine and beer offerings include an aged cava from Catalonia and the Alchemist Beer’s eternally coveted double IPA, Heady Topper.

Right downtown, the Blue Horse Inn is a local landmark that became a bed and breakfast in the 1980s, and it’s hard to beat the experience of floating in its heated outdoor pool overlooking the river. The newly renovated Woodstock Inn & Resort , another central option, offers plenty of luxury amenities like a spa, a tennis court, and an 18-hole golf course; Red Rooster restaurant and Richardson’s Tavern are on the property, too. Toward Woodstock’s western edge, the Lincoln Inn & Restaurant features its own beautiful views of the Lincoln Covered Bridge, and the restaurant’s ever-changing tasting menus draw plenty of discerning diners.

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10 Of The Most Unique Places To Visit In Vermont

• Visit the Ben & Jerry's Flavor Graveyard and pay homage to retired ice cream flavors like Makin' Whoopee Pie and Economic Crunch. Best time to visit is in the summer for a factory tour and ice cream tasting.
• Explore the Museum of Everyday Life in Glover and indulge in nostalgia by viewing exhibits of vintage detergent boxes and toothpaste tubes. Best time to visit is on weekends for special exhibits.
• Experience the unique tradition of the Woodstock Town Crier in Vermont's most idyllic fall town. Witness the daily bell ringing at 5:55 pm in the summer and enjoy the old-time charm of Woodstock.

The New England state of Vermont is known for its quaint small towns for weekend trips , rolling green mountains, maple syrup, and some of the best fall foliage in the US. But beyond the quintessential Vermont imagery lie some incredibly unique and unexpected sights.

From a graveyard where retired Ben & Jerry's ice cream flavors are laid to rest to a museum dedicated to the mundane objects of everyday life, Vermont offers many off-the-beaten-path attractions that most tourists never discover.

Forget busy Burlington and mainstream Stowe. To experience the truly singular side of the Green Mountain State, add the following most unique places in Vermont to visit to the vacation itinerary and discover some of the many hidden gems on the East Coast.

Ben & Jerry's Flavor Graveyard

At the Ben & Jerry's factory in Waterbury, Vermont, devoted ice cream lovers can pay homage to flavors of the past in the Flavor Graveyard. Retired ice cream varieties like Makin' Whoopee Pie, Dastardly Mash, and Economic Crunch lie "dead and buried" under wittily written gravestones.

The tongue-in-cheek memorial is next to the Ben & Jerry's production plant where travelers can take a factory tour and sample today's popular flavors. It's easily one of the most unique attractions in Vermont!

• Landmarks: Gravestones for retired ice cream flavors like Makin' Whoopee Pie and Economic Crunch
• Best Time to Visit: Summer, when people can take a factory tour and enjoy an ice cream after
• Things to Do: Take a factory tour, sample new ice cream flavors, visit the Flavor Graveyard

Related: What Is A Creemee? Here's What To Know About The Vermont-Only Ice Cream

The Museum Of Everyday Life

For a truly singular experience in one of the most unique museums in Vermont, head to the tiny town of Glover and visit the Museum of Everyday Life. This quirky collection contains over 7,000 items that capture the mundane objects of American life in the 20th century.

Exhibits like vintage detergent boxes, old toothpaste tubes, and 1970s Tupperware aim to provoke nostalgia and observations about consumerism and culture. This overlooked museum offers an amusing look at everyday artifacts many take for granted.

• Landmarks: Collection of over 7,000 mundane 20th-century objects
• Best Time to Visit: Weekends when they have special exhibits
• Top Attractions : Vintage detergent boxes and toothpaste tubes that provide a nostalgic look at everyday artifacts

Woodstock Town Crier

Vermont's most idyllic fall town, Woodstock , has an unusual daily ritual: the sounding of the Town Crier Bell. Every day in the summer at 5:55 pm, Woodstock's official Town Crier appears on the Village Green wearing a colonial costume and rings a large bell while reciting a traditional proclamation.

The tradition dates back over 100 years and continues to delight visitors who gather to witness this iconic Vermont custom. Travelers staying overnight in Woodstock can experience a bit of old-time Vermont charm at this brief but lively event.

• Landmarks: Costumed Town Crier, large bell
• Best Time to Visit: Summer at 5:55 pm for the daily bell ringing
• Things to Do: Watch the Town Crier's recital, explore Woodstock, stay overnight to catch the event

Related: Visit Woodstock, New York & Do These 10 Awesome Things

The Old Round Church In Richmond

Built in 1812, the Old Round Church in Richmond, Vermont, is a rare example of 16-sided architecture. The circular design was chosen for its acoustic properties as well as symbolic meaning. Visitors enter through an imposing wooden vestibule into a soaring open sanctuary. The church interior has original box pews, a wine-glass style pulpit, and a wooden balcony.

Guided tours provide a close look at the fascinating architecture and history of this unique Vermont church. The adjacent cemetery contains gravestones dating back to the Revolutionary War.

• Landmarks: Circular 16-sided church, historic box pews and pulpits
• Tour Duration: 30-45 minutes for a guided tour
• Top Attractions : Architectural design, original antique interiors, adjacent Revolutionary War cemetery

The American Precision Museum

The American Precision Museum in Windsor celebrates an invention that revolutionized manufacturing in the early 1800s. At the nearby former Robbins & Lawrence factory, inventor Thomas Blanchard created one of America's first modern assembly lines and mass-produced interchangeable, identical parts using large machines.

Travelers can explore seven floors of exhibits on New England's first mechanized factory, examine antique machine tools, and gain an appreciation for how this technology fueled the Industrial Revolution. Interactive displays let visitors see demonstrations of the historic manufacturing process.

• Landmarks: Antique machine tools and old factory equipment
• Things to Do: Explore 7 floors of interactive exhibits on manufacturing history
• Top Attractions: See demos of antique machines and learn about America's first assembly line

Knight's Spider Web Farm

Crawling with creativity, the Spider Web Farm in Williamstown, Vermont, is home to the world's largest spider web collection. Artist Dona Dunn has been collecting, cataloging, and curating spiderwebs for over 20 years. Her nature-inspired folk art gallery displays over 5,000 different spider web types sourced from all over the world.

Visitors can take self-guided or private tours through rows of eclectic barns housing this extensive arachnid archive. For those seeking quirky roadside attractions in Vermont, this place spins an unforgettable web.

• Landmarks: Collection of over 5,000 different spider webs
• Length/Distance: 1-mile self-guided tour through barns
• Top Attractions: Observe the diversity of spider webs, browse the quirky folk art gallery

Bellows Falls Petroglyphs

Although Vermont is not ranked among the best places to see petroglyphs in America , the state does have some spots to see these ancient sketches. Etched into the rocky banks of the Connecticut River are ancient rock carvings theorized to be Native American petroglyphs. The carvings depict faces, figures, footprints, and symbols.

They were rediscovered in the 1920s near Bellows Falls, although their precise origins remain unknown. A steep climb down the cliff face via metal staircases and ladders provides access to view the petroglyphs up close.

This fascinating archeological site in Vermont offers a glimpse into the state's indigenous roots and is believed to be the largest collection of Native rock carvings in the state.

• Landmarks : Ancient rock carvings depicting faces, figures, and symbols
• Difficulty Level: Moderate hike down steep cliff via ladders and staircases
• Top Attractions: View Native American rock carvings, explore Vermont's indigenous history

Related: America's Oldest Petroglyphs Are 3x Older Than The Pyramids

The Forgotten Village Of Greenbanks Hollow

Nestled deep in the remote Green Mountains lies the abandoned village of Greenbank's Hollow. In the 1930s, the government purchased and evacuated residences in the area to establish Greenbank's Hollow as watershed land. The once-vibrant logging village became one of the ghost towns in Vermont, seemingly frozen in time, with empty homes, shops, and railroad infrastructure slowly being reclaimed by nature.

Adventurous hikers can explore this eerie lost village, complete with rusty equipment, moss-covered buildings, and glimpses into the region's lumber history. The Wampahoofus Trail is also a great option for those hunting the region’s mythical creature . There are several glamping spots in the Green Mountains for those planning to stay for a few days.

• Landmarks : Abandoned 1930s logging village, empty homes and buildings
• Length/Distance: 2 miles round trip hike into a remote village
• Top Attractions: Explore eerie abandoned town frozen in time, glimpse logging history

The Bread And Puppet Museum

Glover, Vermont, is also home to the Bread and Puppet Museum , housed in a red brick building containing decades of theatrical performances. The politically radical puppet troupe Bread and Puppet Theater was founded in the 1960s and is best known for its larger-than-life papier-mâché puppets.

The museum's exhibits feature instruments from past anti-war parades, circuses, and pageants, along with posters and videos documenting the group's productions. Travelers can watch Bread and Puppet rehearsals and tour workshops where the magic happens.

• Landmarks: Collection of giant paper-mâché puppets from political theater performances
• Tour Duration : 1-hour self-guided tour
• Things to Do: View puppets, watch rehearsals, time puppet-making workshops

Junk Locomotive

In the self-proclaimed "Best Lil' Town in Vermont'' lies a whimsical roadside attraction. The town of Chester erected a full-sized locomotive sculpture completely made from scraped metal and junk parts. Constructed by local resident Tom Boisvert, this quirky junk locomotive delights visitors who stop by the picturesque Stone Village Museum.

The recycled train engine symbolizes Chester's railroading history and demonstrates Vermont's strong folk art heritage - proving that creativity and community can transform piles of junk into an unforgettable work of art.

• Landmarks: Full-sized train sculpture made from recycled scrap metal
• Best Time to Visit: Summer, when you can browse the outdoor Stone Village Museum
• Top Attractions: Whimsical recycled folk art sculpture represents Chester's railroad history

Top Things to Do in Woodstock, VT - Woodstock Must-See Attractions

Things to do in woodstock, explore popular experiences, tours in and around woodstock.

Day Tour through Stowe, Vermont

7-Hour Tour Through Montpelier and Mad River Valley, Vermont

Brewery & Spirits Tour

Superman Zipline Tour in Morningside

WW2 Small Arms Experience

Colonial Flintlock Musket Experience

2 Hour Forest Immersion Retreat in Woodland Sanctuary

3 Day Reiki Certification Retreat in Vermont

Mountain Top Zipline Tour in Morningside Flight Park

Lake Tarleton Guided Paddle

Top attractions in woodstock.

Other Top Attractions around Woodstock

What travellers are saying

• 7 Cutest Small Towns In New England To Visit In 2024

New England , named by the English seafarer Captain John Smith, is the collective term for six northeastern United States - Massachusetts, Rhode Island, Connecticut, Vermont, New Hampshire, and Maine. It’s one of the most photogenic regions in the US, particularly in fall when you’re likely to see your social media feed crowded with classic New England scenes of picturesque small towns nestled amid autumnal foliage and rolling hills. The area’s charming villages are worth a visit any time of year, equally welcoming in the winter wonderland of the holidays and the sun-drenched days of high summer. Quaint main streets, historic architecture, and gorgeous scenery — plan a trip to New England in 2024 and it’ll quickly become a family favorite.

Concord, Massachusetts

The hometown of author Louisa May Alcott and naturalist Henry David Thoreau, Concord is a pretty river town with a rich history that’s reflected in its tree-lined streets and pretty parks. Stroll scenic walking paths at the Minute Man National Historic Park and browse exhibits from the era of the American Revolution as well as artifacts from the Alcott family. Another historic landmark, Walden Pond, is a 136-hectare park which will be familiar to fans of Thoreau’s writings. There's a replica of the author’s single-room cabin on the grounds. Once you’re done exploring, cool off in the 102 ft deep pond which is open for swimming and boating. Back in town, Concord has lots to offer in its lively downtown where you’ll find arty boutiques, busy dining patios, and eye-catching architecture. Visit in June to experience the town’s largest festival, Market Days, a three-day music, entertainment, food, and shopping bonanza.

Woodstock, Vermont

Located in central Vermont, on the Ottauquechee River, Woodstock is a classic New England town, founded in 1761. It’s also home to Vermont’s first National Park, the Marsh-Billings-Rockefeller National Historical Park. Here you’ll find a sprawling mansion, landscaped gardens, and the stunning Mount Tom forest. Drive the backroads around Woodstock for more quaint, historic attractions including the Calvin Coolidge Memorial Homestead, the Old Constitution House, and the Justin Morrill Historic Homesite. Have a truly rural experience at The Billings Farm & Museum, an outdoor museum showcasing farm life over the past 200 years. Visit the restored 1890 Farmhouse, sample the working dairy farm’s famous raw-milk cheddar, or say hi to the local livestock with hands-on demonstrations and exhibits.

Bethel, Maine

Bethel is a sleepy Maine town near the Appalachian Mountains known as a premier destination for skiers and nature-lovers. The town is a great base for exploring the White Mountain National Forest which offers year-round adventure from hiking and kayaking to skiing and snowshoeing. If you’re driving into town via Route 5, don’t forget to stop at the Lovejoy Bridge. This classic covered bridge was built in 1868 and is the perfect backdrop for unforgettable vacation photos. In town, stop by the O'Neil Robinson House, built in 1821, and Dr. Moses Mason House, built in 1813, for a glimpse into Bethel life two centuries ago. If you’re thirsty after all that sightseeing, try a small batch craft beer at Steam Mill Brewing, a lively brewpub named after the steam mill located in Bethel in the mid-1900s.

Wickford Village, Rhode Island

It’s no wonder Wickford Village consistently appears in top ten lists of historic small towns. This picture-perfect seaside village is a charming mix of leafy streets, 17th century architecture, and coastal views. Explore downtown’s antique shops and bustling boutiques, sip a coffee at a waterfront patio, whatever you’re in the mood for, Wickford delivers. History fans can view stunning examples of classic Colonial architecture including the Old Narragansett Church, founded in 1706, and the Gilbert Stuart Birthplace & Museum, the 1750 home of the famous artist. You’ll also want to explore Smith’s Castle on the western shore of Narragansett Bay. Built in 1678, this is the oldest surviving plantation house in America and is listed on the National Register of Historic Places.

Stowe, Vermont

Known primarily as a ski resort, Stowe has more to offer visitors than great powder. Near town, you’ll find the charmingly-named Smugglers’ Notch State Park, a beautiful recreation area featuring a wetlands boardwalk, the challenging Hellbrook Trail, and access to Bingham Falls. In town, you’ll find the quaint inns, colonial architecture, and rustic bridges that New England is known for. Be warned, however, the Gold Brook Covered Bridge, built in 1844, is said to be haunted by a lovesick phantom known as Emily. If you’re staying in town, consider the Trapp Family Lodge. Run by the family who inspired the hit musical The Sound of Music, this charming resort offers cross-country skiing, carriage rides, wine tasting, and Austrian-inspired lodgings.

Meredith, New Hampshire

Meredith is a small beach town on the shores of Meredith Bay, which feeds into the largest lake in New England, Lake Winnipesaukee. Enjoy the water from one of the most scenic spots in town, Leavitt Beach. This sandy oasis has the best picnicking and swimming with crystal clear water and views of the wooded shoreline. Downtown, check out Hermit Woods Winery & Eatery, a boutique winery that offers wine tasting, farm-to-table dining, and live entertainment. To pick up local souvenirs, head to the Mill Falls Marketplace, a stunning shopping village with flower gardens, a sculpture walk, waterfront boardwalk, and a 40 ft waterfall.

Mystic, Connecticut

Movie fans will recognize Mystic immediately. This coastal Connecticut town was the setting for the 1988 hit film, Mystic Pizza, starring Julia Roberts. The famous restaurant, which opened its doors in 1973 is still downtown and still open so don’t forget to grab a slice during your visit. Mystic’s fame began long before pizza however. The town was an important seaport in the 19th century and now has three separate historic districts, the Mystic River Historic District, the Mystic Bridge Historic District, and the Rossie Velvet Mill Historic District. It’s also home to one of America’s leading maritime museums — four vessels in the seaport are listed on the National Register of Historic Landmarks. For the best dining and shopping in Mystic explore the Olde Mystic Village, an open-air shopping plaza bustling with restaurants, cafes, and boutique galleries.

New England, Old World Charm

From haunted bridges and famous pizza to colonial homesteads and outdoor adventures, New England’s charming small towns are full of unforgettable experiences. When the pilgrims settled here in 1620, they found a lush land of rugged mountain peaks, grassy foothills, serene lakes, and sandy coastlines. That timeless, natural beauty is still waiting to be discovered today, along with the pioneering spirit of the Pilgrims. Take a trip to New England’s breathtaking small towns this year to discover what you’re missing in the birthplace of America.

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Summer in Vermont

Summer days in Vermont bring family and friends together at the beach, on the lakeshore, or around a campfire. There are as many ways to enjoy the summer season as there are paths that travel through the Green Mountains, whether you’re hiking or biking on a scenic trail or enjoying a road trip on a sunny day. Summer is your gateway to the sense of wonder and well-being that comes with slowing down and taking in your surroundings.

The Long Trail Home

Summer in Vermont: as close to perfect as the Pickett family can get. Kina Pickett’s return home to Woodstock, Vermont includes picking vegetables and flowers with his kids, visiting favorite lakes and swimming spots, and rediscovering the joy of immersing yourself in a community that celebrates the season.

Ways to Get Outside

Summer turns Vermont’s mountains, trails, rivers, and lakes into playgrounds for outdoor enthusiasts.

Water Sports

Vermont’s lakes beckon for kayaking, swimming, paddleboarding, boating, and other water sports. From Lake Champlain, stretching along the western border to Lake Willoughby in the north and Spruce Lake in the southern region, there’s over 800 lakes to explore.

Outdoor Art

Vermont’s outdoor art showcases how Vermont landscapes and towns not only inspire artists, but also become part of the work and the experience of taking it in. Enjoy the fresh air as you explore public art.

Farm Visits

Visiting a Vermont farm can mean spending a few hours petting farm animals and picking produce, or it can be a more immersive experience. Start planning to visit a Vermont farm.

Recreation Paths and Rail Trails 

Vermont’s rail trails and recreation paths are great low-impact ways to explore downtowns, scenic views, and waterfronts. Along the way, there are many opportunities to enjoy a taste of Vermont, from farmstands to farm-to-table dining, breweries to cideries, and more.

A cycling adventure leads travelers through Vermont’s picturesque landscapes, where paved and gravel roads intertwine, connecting charming villages and revealing the state’s storied history.

The end of the trail is only the beginning. With hundreds of mountains, five of them with summits higher than 4,000 feet, offer boundless opportunity for hiking Vermont’s rugged terrain and taking in Green Mountain views.

Vermont’s Hills and Valleys Rock

Summer Events

Signature events rock the Green Mountains all summer long. At county fairs, bring the whole family to play games and feel the adrenaline on the midway rides. Gather at Barre’s Millstone Trails for an elemental experience of fire, music, and art. Whether you head to downtown Burlington for the South End Art Hop, enjoy live music at a festival with the Green Mountains as a backdrop, walk through Brattleboro’s Gallery Walk, or take in the work of local artists, plan your visit around Vermont’s events calendar.

Vermont State Parks

With 55 state parks open year-round, Vermont’s public lands are a gateway to outdoor recreation in the state, and many even rent equipment like boats. Discover camping, hiking, biking, swimming, and some of the Green Mountains’ most beautiful places.

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Scenic Drives

Byways and back roads are some of the best ways to explore the state, meandering through historic downtowns and inviting stops at general stores, farmstands, scenic vantage points, and more.

Itineraries

As you plan your Vermont vacation, itineraries can help you make the most of your experience. Discover long weekend itineraries, regional trip planning guides, and more.

Vermont’s ice cream producers range from innovative makers throughout the state with large operations to stands by the sides of roads offering delicious creemees and scoops of local flavor. Many are open year-round and you can plan a whole trip around visiting and sampling.

Historic Downtown

Vermont downtowns are not just destinations; they are invitations to savor the authentic, diverse, and captivating spirit of the Green Mountain State.

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THE 15 BEST Things to Do in Woodstock

Things to do in woodstock, explore popular experiences, tours in and around woodstock.

Day Tour through Stowe, Vermont

7-Hour Tour Through Montpelier and Mad River Valley, Vermont

Brewery & Spirits Tour

Superman Zipline Tour in Morningside

WW2 Small Arms Experience

Colonial Flintlock Musket Experience

2 Hour Forest Immersion Retreat in Woodland Sanctuary

3 Day Reiki Certification Retreat in Vermont

Mountain Top Zipline Tour in Morningside Flight Park

Lake Tarleton Guided Paddle

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Other Top Attractions around Woodstock

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