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 so unique. Anyone who visits the town of Woodstock is touched by its elegance, small-town feel, four seasons of beauty, and kind local residents.
In 2019, Woodstock was listed among the 27 Most Beautiful Towns in America by 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 the best things to do and top attractions in Woodstock!
- Most significant landmark – Billings Farm & Museum Store
- Best park – Marsh-Billings-Rockefeller National Park
- Best free activity – Visiting the local covered bridges
- Best activity for kids – Ottauquechee River
- Best activity for adults – Hiking or skiing Mount Tom
- Best food – Lincoln Inn & Restaurant
- Best nightlife – Au Comptoir
- Best all-around accommodation – Woodstock Inn
Best & Fun Things to do in Woodstock, VT
1. 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, with 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 that was 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. As a working dairy farm, Billings Farm has been producing artisan cheese for over 150 years. You can purchase the delicious cheese at the farm store and many other locations in Vermont.
For adults, Billings Farm offers many programs and educational classes that teach sustainable living skills. There are art classes, music concerts, a film series, and much 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. There are also youth field trips, story hours for toddlers, and much more.
See Related: Fun & Best Things to Do in Dorset, Vermont
2. Woodstock Inn & Resort
Address: Fourteen The Green, Woodstock, VT 05091,
There really 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 in search of 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 barre at the Athletic Club, along with two swimming pools for guests to enjoy.
In the winter months, go ahead and 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 that’s been nationally ranked for its 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 or explore the grounds on bikes, or go for a fly-fishing lesson with one of the resort’s expert anglers.
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3. Taftsville Covered Bridge
Address: Woodstock, VT 05091
If there’s one thing Vermont and New England are known for, it’s their covered bridges. In fact, 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 own 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 the state of 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 that can be 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.
4. Norman Williams Public Library
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 among books and media and truly has something for any reader within its historical walls. This site is now known as The Green in Woodstock, and it’s 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. For older children and adults, the library offers art classes, movie screenings, crafts, art talks, lectures, and much more every week.
See Related: Fun & Best Things to Do in Middlebury, Vermont
5. Quechee Gorge
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 and the Quechee Gorge, along with the Quechee Gorge Bridge.
On one side of the bridge, you’ll find the Visitor Center and a gift shop with many Vermont souvenirs. You can park on the other side and walk across the bridge, taking in 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
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 take place each week.
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: Fun & Best Things to Do in Bennington, Vermont
7. Lincoln Inn & Restaurant
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 is a solid choice offering incredible dining and unique views of the Lincoln Covered Bridge, which is on the national register of historic places.
When it’s time for a meal, the restaurant offers unique, delicious dishes that are sure to be a memorable part of your trip to New England. Listed in the nation’s 10 best restaurants of 2016 by Forbes, 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 truly 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 with a walk around the six acres of grounds, sit by the Ottauquechee River, or rest on the outdoor patio furniture.
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 in the stunning Vermont countryside from your window and spend time unwinding in the library.
8. Sugarbush Farm
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, as well as 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 that 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: Fun & Best Things to Do in Brattleboro, Vermont
9. F.H. Gillingham and Sons General Store
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 continue to maintain his ethics of integrity, quality, and community 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
The Ottauquechee River is located in central Vermont. It’s about 41 miles long and flows through Woodstock, Pomfret, and many other Vermont towns to eventually 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 so many ways to enjoy in this beautiful river that flows right 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: Fun & Best Things to Do in Montpelier, Vermont
11. Mount Tom & Marsh Billings Rockefeller National Park
Address: Marsh-Billings-Rockefeller National Park, Woodstock, VT 05091
Looking for some hiking trails on your Woodstock vacation? Located within the Marsh Billings Rockefeller National Park, Mount Tom is a 4-mile loop trail and small peak located near Woodstock. It’s of moderate difficulty and takes most hikers about 2 hours to complete. There are numerous trails you can pick up on Mount Tom, including Faulkner Trail, which will lead 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 what your mode of transportation is, 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 you’re visiting the Marsh Billings Rockefeller National Park, don’t skip a stop at the Carriage Barn Visitor Center. Take in the beautiful sandstone mansion, another one 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 truly majestic outdoor experience, no matter the season. So here I am, recommending the heck out of it.
12. Middle Covered Bridge
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, we think the Woodstock bridges are some of the most charming and beautifully constructed structures in the state. That’s why we included two of them. You’re welcome.
See Related: Fun & Best Things to Do in Manchester, Vermont
13. Explore Woodstock Village
In the town of 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 of all kinds, 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 that come with staying in a full-sized house.
14. Quechee Covered Bridge
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 if you want to spend some time taking in the scenery, snapping some photographs, and admiring the Quechee Gorge. To the west of the Quechee Covered Bridge, you’ll find an incredible view of the dam, waterfall, and nearby power plant and glass-blowing factory.
See Related: Fun & Best Things to Do in Stowe, Vermont
15. Woodstock Town Hall Theater
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 the town of Woodstock.
Today, the Town Hall Theater features popular movies and is often home to 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
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 historic places in Vermont that can be enjoyed by the entire family.
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 sto by the museum store for gifts!
Guests can explore the former President’s 1924 Summer White House exhibit, which includes the original desk he used when taking meetings. Visitors can also wander down the one-mile nature trail just north of the Coolidge Museum and Education Center for some fresh air.
What are the best tourist attractions in Woodstock, Vermont?
Enjoy an incredible farm-to-table meal at Cloudland Farm right outside of the town of Woodstock. Soak in the outdoors by hiking or snow-shoeing around Mount Tom at Marsh Billings Rockefeller National Historic Park and enjoy stunning views of the Green Mountains, or take in the breathtaking views of Quechee Gorge.
What is the best thing to do with kids in Woodstock, Vermont?
Kids of all ages can have a blast in Woodstock. When it’s warm, swim or fish in the Ottauquechee River. You can jump in the car and go on a road trip and explore the many covered bridges in the area or meet the animals and learn all about farm life at Billings Farm.
What are some things to do in Woodstock when it’s raining?
The rain can’t stop you in Woodstock! Head indoors and catch a movie or performance at the Town Hall Theater. Stay dry and explore the history of Vermont in the Norman Williams Public Library, one of the town’s oldest buildings.
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