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16 Best Things to Do in Woodstock, Vermont

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Since its establishment in 1761, Woodstock, Vermont, has been a symbol of entrepreneurship, cultural heritage, and a hardworking community that welcomes visitors from all over the United States.

Today, Woodstock’s charm lies in its artisans, makers, farmers, and artists, who make the small community unique. Anyone who visits the town of Woodstock is touched by its elegance, small-town feel, four seasons of beauty, and kind residents.

In 2019, Woodstock was listed among the 27 Most Beautiful Towns in America by CN Traveler Magazine, and we have a hard time disagreeing with their assessment.

From its numerous famous covered bridges, historical monuments, and glorious surrounding mountains, there are hundreds of reasons to visit this quaint town in New England, with its beauty taking center stage.

Many visitors flock to Woodstock for its quintessential New England charm: skiing and snow-shoeing in the winter, foliage and outdoor festivals in the fall, and thrilling hiking, fishing, and swimming spots in the spring and summer. But why should you visit Woodstock? Read on as we uncover some of Woodstock’s best things to do and top attractions!

TL;DR

  • Most significant landmark – Billings Farm & Museum Store
  • Best park – Marsh-Billings-Rockefeller National Park
  • Free activity – Visiting the local covered bridges
  • Activity for kids – Ottauquechee River
  • Activity for adults – Hiking or skiing Mount Tom
  • Place to eat – Lincoln Inn & Restaurant
  • Nightlife – Au Comptoir
  • Place to stayWoodstock Inn

Things to Do in Woodstock, Vermont

1. Billings Farm and Museum

House surrounded with trees at at Billings Farm and Museum
Billings Farm and Museum / Billings Farm and Museum

Address: 69 Old River Rd, Woodstock, VT 05091

Billings Farm and Museum is a working farm in Woodstock that offers interactive farm life exhibits and demos for visitors. Since 1871, Billings Farm has been known for its jersey cow breeding, advanced farming techniques, and impressive ownership by Frederick Billings, a Vermont local.

If you plan to visit Billings Farm, you’ll likely encounter the jersey cows, as well as horses, sheep, goats, and chickens that live on-site. Visitors can tour the Billings Farm Museum in the historic barns, which have fascinating artifacts, including hand tools, farm equipment, oral histories, and more.

After you see the Billings Farm Museum, take a gander at the 1890 Farm Manager’s House, with its cutting-edge (at the time) farming equipment and technology used on Billings Farm, from creamery equipment to central heat and an indoor bathroom. Tour the General Store and see what townspeople bought nearly two centuries ago for their homes.

There are farmstead gardens to explore at Billings Farm and a 20,000-square-foot Sunflower House display that will take your breath away. Billings Farm has produced artisan cheese for over 150 years as a working dairy farm. You can purchase the delicious cheese at the farm store and many other locations in Vermont.

Billings Farm offers many programs and educational classes for adults that teach sustainable living skills. There are art classes, music concerts, a film series, and more. For the kiddos, Billings Farm is host to many weekly camps in the summer months where kids can get up close and personal with farm animals. Youth field trips, toddler story hours, and much more are also there.

See Related: Things to Do in Dorset, Vermont

2. Woodstock Inn & Resort

Trail leading to Woodstock Inn & Resort building
Woodstock Inn & Resort / Booking.com

Address: Fourteen The Green, Woodstock, VT 05091,

There isn’t a finer establishment in all of Vermont than the Woodstock Inn & Resort. Featuring stunning rooms, including a legacy suite honoring the inn’s owner, Mary French Rockefeller, your stay at Woodstock Inn will be elegant, relaxing, and memorable. And there’s real history attached here, too!

The Woodstock Inn was originally built in 1892 as an inn but quickly grew in popularity with New England’s growing tourism scene. Affluent travelers from all over the country came to Vermont to witness the state’s beauty and natural grandeur – and to attend the Inn’s wild winter parties it became famous for!

With ever-growing influxes of guests searching for the perfect Vermont vacation, it wasn’t long before the Inn expanded into a resort.

Today, the Woodstock Inn & Resort is a great place to spend a day or stay during a Woodstock getaway. The resort has four distinct restaurants that serve farm-fresh cuisine with locally harvested ingredients and seasonal cuisine, craft cocktails, and an exciting atmosphere that will keep you satisfied and entertained.

While staying at the resort, guests can enjoy the incredible amenities, including the on-site spa. Get a massage or facial and soak in the feelings of rejuvenation that can only happen on vacation. If you’re interested in outdoor sports, the resort offers tennis, yoga, and a barre at the Athletic Club, as well as two swimming pools for guests.

In the winter months, grab your skis and head to Saskadena Six Ski Area for a day on the slopes for the whole family. You can hit the links at the nearby Woodstock Country Club, a premier 18-hole course nationally ranked for excellence.

To keep the kids entertained, they can get up close and personal with falcons and barn owls through a unique Falconry experience on the resort grounds. Take a guided hike, explore the grounds on bikes, or go for a fly-fishing lesson with one of the resort’s expert anglers.

See Related: Where to Stay in Utah to Visit National Parks Best Areas

3. Taftsville Covered Bridge

Taftsville Covered Bridge with natural landscape backdrop
rabbit75_fot / Adobe Stock

Address: Woodstock, VT 05091

If there’s one thing Vermont and New England are known for, it’s their covered bridges. Vermont has more covered bridges per square mile than any other state in the country! You’ll find them all over the place, and they’re all unique with their history and interesting tall tales.

The Taftsville Covered Bridge in Woodstock is the oldest covered bridge in Windsor County and the second-longest covered bridge in Vermont. Standing 189 feet long and 200 feet tall, the Taftsville Covered Bridge is right beside the Ottauquechee River and is an iconic tourist attraction in the area.

The Taftsville Covered Bridge was built in 1836, and its architecture is believed to reflect the covered bridges found in Switzerland. Whether you want to experience driving on a covered bridge or park and get an up-close view, both are possible at the Taftsville Covered Bridge.

As one of the state’s most historic covered bridges, Taftsville Covered Bridge is a must-see for New England history buffs and Swiss or Vermont bridge lovers alike.

See Related: Where to Stay in Vermont

4. Norman Williams Public Library

Norman Williams Public Library books and interior
Norman Williams Public Library / Facebook

Address: 10 The Green, Woodstock, VT 05091

Since 1883, the Norman Williams Public Library has welcomed the public through its doors to learn, explore, and educate through lectures, books, presentations, exhibits, and more. Gifted by Dr. Edward H. Williams, the Norman Williams Public Library is named after his father. The library was built on the site of his parent’s home in Woodstock.

Norman Williams Public Library features over 70,000 offerings in books and media, and it truly has something for any reader within its historic walls. This site is now known as The Green in Woodstock, a popular gathering space in the city.

The library is a local icon and is made from beautiful pink sandstone. It draws in locals and those visiting Woodstock to experience a unique piece of New England history and literature within its walls.

The library welcomes adults and children alike, with a lovely Children’s Room for quiet time, reading, story hours, and summer reading events for kids of all ages. The library offers art classes, movie screenings, crafts, art talks, lectures, and much more for older children and adults every week.

See Related: Things to Do in Middlebury, Vermont

5. Quechee Gorge

Bridge above Quechee Gorge surrounded with trees
Halo Creative / Adobe Stock

Located in Quechee, Vermont, on Route 4, the Quechee Gorge is a stunning site about 15 minutes east of Woodstock. Known as one of Vermont’s most spectacular and jaw-dropping natural wonders, Quechee Gorge features several waterfalls, hiking trails, and many lookout points where you can marvel at “Vermont’s Little Grand Canyon.

The gorge itself is 165 feet deep, the deepest in the state of Vermont. At the bottom of the gorge, you’ll find the Ottauquechee River, a popular swimming area that locals love. Visitors will enjoy amazing views of the river, the Quechee Gorge, and the Quechee Gorge Bridge.

You’ll find the Visitor Center and a gift shop with many Vermont souvenirs on one side of the bridge. You can park on the other side and walk across the bridge, enjoying the incredible views below and all around you. For an amazing stay near the village of Quechee, consider booking this awesome country townhome with mountain views.

6. The Village Green

Establishment in Village Green, Woodstock, Vermont
Ken Lund / Flickr

Address: The Green, Woodstock, VT 05091

To experience life like the locals, spending time in downtown Woodstock Village is a great place to start. Visit the town Green, often called Woodstock’s Central Park, where many events occur weekly.

From June to October, the Market on the Green is an outdoor Farmer’s Market with over 30 local vendors selling cheese, maple syrup, fruits and veggies, bread, meats, and other tasty treats from local farms. You’ll meet many local business owners and chat with families who enjoy the small-town lifestyle.

You can’t miss the Gallery on the Green, one of the best art galleries in town that features local artists in a variety of mediums. After you visit the Green, wander through downtown Woodstock and visit the antique shops and eclectic retailers, or stop for a bite in one of the many delicious restaurants.

Looking for an authentic stay in downtown Woodstock? Try the quaint Village Green B&B, right in the middle of the town and easily accessible by foot.

See Related: Things to Do in Bennington, Vermont 

7. Lincoln Inn & Restaurant

Lincoln Inn & Restaurant building during winter
Lincoln Inn & Restaurant / Facebook

Address: 2709 West Woodstock Rd, Woodstock, VT 05091

When searching for a place to eat and stay during a blissful New England retreat, Lincoln Inn & Restaurant offers incredible dining and unique views of the Lincoln Covered Bridge on the National Register of Historic Places.

When it’s time for a meal, the restaurant offers unique, delicious dishes that will surely be a memorable part of your trip to New England. The Lincoln Inn Restaurant offers a 7-course chef’s tasting menu with seasonal items, wine pairings, and an elegant vibe. With a Michelin Star-trained European chef, be sure that only the most exquisite dishes are offered at the Lincoln Inn restaurant.

As you can imagine, the menu items include only the freshest and seasonal ingredients, all grown locally by family farms in the Woodstock area. Chef Jevgenija Saromova is an artist who prepares a fantastic culinary experience that encompasses perfect texture, taste, ambiance, and flavor to create the most memorable meal you’ll ever have. Guests can enjoy the outdoors by walking around the six acres of grounds, sitting by the Ottauquechee River, or resting on the outdoor patio.

Better still, after a superb meal and a quiet walk to help it go down, you can spend the night at the Lincoln Inn. As for a cozy place to rest your head, it doesn’t get much better! Relax as you take the stunning Vermont countryside from your window and unwind in the library.

8. Sugarbush Farm

Sugarbush Farm horses and skyline
Management / TripAdvisor

Address: 591 Sugarbush Farm Rd, Woodstock, VT 05091

Built in 1865, Sugarbush Farm is a working dairy farm in the rural region right outside of Woodstock proper. The farm is known for its cheese and maple syrup production and is one of the most popular attractions in the area, welcoming around 40,000 visitors each year. Sugarbush Farm consists of 500 acres in central Vermont and is definitely worth visiting if you’re staying in Woodstock.

Guests can sample over 15 variations of cheese, including their six-year aged sharp cheddar and a naturally smoked cheese that will knock your socks off. Then tour the sugarhouse where the maple syrup is made and witness firsthand how the staff creates this tasty, sugary substance. You can also sample various grades of maple syrup and their in-house jams, mustards, and many other spreads.

If you’re hungry, stop at the farmhouse gift shop to buy cheese, maple syrup, and many other local delicacies you might have tasted during your visit. Best of all, you can enjoy stunning views at Sugarbush Farm any time of year. Be sure to stop and say hello to the friendly goats who live on the farm while you’re there!

See Related: Things to Do in Brattleboro, Vermont

9. F.H. Gillingham and Sons General Store

F.H. Gillingham and Sons General Store building across the road
F.H. Gillingham and Sons General Store / Facebook

Address: 16 Elm Street, Woodstock, VT 05091

Now’s about the time to do some serious souvenir hunting. Opened by Frank Henry Gillingham in 1886, F.H. Gillingham and Sons General Store is one of the most historic stores in Woodstock. Today, Frank’s descendants still run the store and maintain his integrity, quality, and community ethics over 130 years after it first opened.

In the early days, local shoppers came in for hardware, molasses, and other goods for their homes and farms. Nowadays, locals and visitors alike come to F.H. Gillingham for a step back in time and a rich history lesson on the happenings of Woodstock in the early 1900s. The store contains an archive section with ample photographs and artifacts from Woodstock’s previous generations, and there’s so much to learn.

Stepping into the General Store on the village green will excite every one of your senses. You can browse for clothing and toys, books, outdoor gear, and baby products.

If you’re looking for snacks and food, there are incredible local products from vendors in Woodstock and its surrounding areas. Choose from an elite selection of Vermont cheese, wine, maple syrup, honey, penny candy, and more.

Whether you’re looking for something in particular or just coming to Gillingham’s to browse, we have no doubt you’ll leave with pockets filled with treats and local goodies that you can’t find anywhere other than Woodstock!

10. Ottauquechee River

Ottauquechee River flowing through green countryside in historic Woodstock Vermont
Alan Klehr/Danita Delimont / Adobestock

The Ottauquechee River is located in central Vermont. It’s about 41 miles long and eventually flows through Woodstock, Pomfret, and many other Vermont towns to connect to the Connecticut River. There are many spots in Woodstock to access the river, the most popular being East End Park in Woodstock, which offers a picnic area and three-mile hiking trails near Billings Farm.

Throughout Woodstock, visitors can access the river for many thrilling water activities. From canoeing and kayaking to fly fishing and swimming, there are many ways to enjoy this beautiful river flowing through town.

If you’re looking to swim and spend the day on the river shores, the best access points include the lawn of the Woodstock History Center for wading, Elm Street Bridge, and between the Woodstock Recreation Center and the Little Theater for a great spot for families to hang out, enjoy the small rapids, and splash in the waist deep water.

Looking for a place to stay with river views in Woodstock? For a cozy modern farmhouse in Woodstock, consider this modern farmhouse vacation rental.

See Related: Things to Do in Montpelier, Vermont

11. Mount Tom & Marsh Billings Rockefeller National Park

Marsh Billings Rockefeller National Historical Park woodshed
Reimar / Adobe Stock

Address: Marsh-Billings-Rockefeller National Park, Woodstock, VT 05091

Looking for some hiking trails on your Woodstock vacation? Mount Tom is a 4-mile loop trail and small peak near Woodstock in the Marsh Billings Rockefeller National Park. It’s of moderate difficulty and takes most hikers about 2 hours to complete. You can pick up numerous trails on Mount Tom, including Faulkner Trail, leading you to a stunning view of the Green Mountains.

Many visitors enjoy exploring Mount Tom on cross-country skis in the winter and by foot or horseback in the spring, summer, and fall. No matter your mode of transportation, you’ll enjoy breathtaking views of Woodstock Village, the Ottauquechee River, and surrounding mountain towns.

You can expect to see wildlife on your journey, including many variations of birds, deer, squirrels, toads, and even salamanders, along with a diverse collection of plants, ferns, and trees. During fall foliage season, you can witness the leaves change on Mount Tom, and it will take your breath away!

While visiting the Marsh Billings Rockefeller National Park, don’t stop at the Carriage Barn Visitor Center. Take in the beautiful sandstone mansion, another of Woodstock’s most historic places. It was the boyhood home of environmentalist and Woodstock native George Perkins Marsh and was later purchased by Frederick Billings, a founder of the Northern Pacific Railroad, in 1869.

The history-rich home and acreage is another site on the National Register of Historic Places for its cultural and local history and contributions to the area. Anyone who has visited Woodstock will surely recommend Mount Tom and its rolling hills for a majestic outdoor experience, no matter the season. So here I am, recommending the heck out of it.

12. Middle Covered Bridge

Middle Covered Bridge during winter in Woodstock, Vermont
demerzel21 / Adobe Stock

Address: Mountain Avenue, Woodstock, VT 05091

If witnessing as many covered bridges as possible is a goal on your New England road trip, we recommend adding the Middle Covered Bridge to your list! Located near Woodstock Inn and the downtown area, the Middle Covered Bridge spans 140 feet and is likely the most popular bridge in the New England village of Woodstock. The lattice truss design is unique and quite a sight to see firsthand.

Middle Covered Bridge was built in 1969 to replace an iron bridge from the 1800s. It was made with wooden pegs instead of nails and offers a separate walkway for foot traffic who want to walk the Middle Bridge and experience its old-world charm.

While there are many more covered bridges in New England, the Woodstock bridges are some of the state’s most charming and beautifully constructed structures. That’s why we included two of them. You’re welcome.

See Related: Things to Do in Manchester, Vermont

13. Explore Woodstock Village

view of the town of Woodstock Vermont
ericurquhart / Adobe Stock

In Woodstock Village, you’ll experience the quaint small-town vibe you picture in Vermont while simultaneously enjoying the perks of a big city. With 30 shops, over 20 restaurants, several gyms, places of worship, genuinely pretty architecture, many walkable paths, and green spaces, Woodstock Village is a wonderful part of town to explore.

If you’re in the mood to shop, you can find local stores and boutiques selling unique clothing, outdoor gear, home decor, jewelry, art, and unique souvenirs to commemorate your Woodstock getaway. As for food, you won’t find better dining options in Vermont than in the Woodstock area. Everyone loves eating at Mon Vert Cafe, with its rustic feel-good food and coffee.

Craving a craft beer? Pop in at Woodstock Hops N’ Barley for locally brewed IPAs and sours and an impressive wine collection. You could grab a nightcap at Au Comptoir, from craft cocktails like the Polar Plunge, Ginger margarita, or the Manhattan black. For a convenient stay near Woodstock Village, book this charming and spacious country home for your visit to New England and enjoy the amenities of a full-sized house.

14. Quechee Covered Bridge

Historic covered bridge over the Ottauquechee River
vermontalm / Adobe Stock

Address: 4 Waterman Hill Rd, Quechee, VT 05059

So, we saw Middle Covered Bridge and Taftsville Covered Bridge, and you’re here, telling me you want to see another covered bridge? Jeepers. Tough customer.

Alright, alright, message received. Just outside Woodstock lies the quiet town of Quechee, home to the Quechee Covered Bridge. Satisfied?

Built in 1970, Hurricane Irene partially destroyed this two-lane steel bridge in 2011. Fortunately, the bridge has since been restored to its former glory (and actually extended another 15 feet in length) and draws in many tourists to witness its Vermont charm for themselves. Visitors can walk the length of the bridge on the pedestrian walkway or drive through it on their way into town.

There’s plenty of parking to take in the scenery, snap some photographs, and admire the Quechee Gorge. To the west of the Quechee Covered Bridge, you’ll find an incredible view of the dam, waterfall, nearby power plant, and glass-blowing factory.

See Related: Things to Do in Stowe, Vermont

15. Woodstock Town Hall Theater

Woodstock Town Hall Theater builing front
Woodstock Town Hall Theater / Facebook

Address: 31 The Grn #2, Woodstock, VT 05091

If you visit Woodstock and want to experience a film in one of the town’s historic buildings, a stop at Woodstock Town Hall Theater is a must! Originally opened as an opera house (of all things) in downtown Woodstock in 1900, the theater is designed with neoclassic historic architecture and is a hub of cultural excellence for Woodstock.

Today, the Town Hall Theater features popular movies and often hosts weddings, corporate events, and musical performances. It also hosts many local events throughout the year, including youth musicals and dance performances, local shows and plays, fairs, and much more.

16. President Calvin Coolidge State Historic Site

President Calvin Coolidge State Historic Site houses and skyline
Management / TripAdvisor

Address: 3780 VT-100A, Plymouth, VT 05056

Located about 15 minutes from Woodstock is the birthplace and boyhood home of President Calvin Coolidge, 30th U.S. President, in Plymouth Notch, Vermont. Calvin Coolidge’s home and surrounding sites in Plymouth Notch are important historical places in Vermont that the entire family can enjoy.

Aside from the family home, you can also see the Coolidge Homestead, Union Christian Church, Schoolhouse, and Plymouth Cemetery nearby. There are several exhibits on site as well, including the Calvin Coolidge Museum, which contains artifacts, diaries, and media from Coolidge’s time as president. Don’t forget to stop by the museum store for gifts!

Guests can explore the former President’s 1924 Summer White House exhibit, including the original desk he used for meetings. Visitors can also wander the one-mile nature trail just north of the Coolidge Museum and Education Center for fresh air.

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