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.
