Last Updated on July 9, 2023
If you closed your eyes and tried to picture the perfect New England village, you would likely visualize Woodstock. Once touted as “The Prettiest Small Town in America” by Ladies Home Journal Magazine, Woodstock most certainly lives up to all the hype.
An authentic slice of early nineteenth-century Americana stands boldly between the rolling mountain landscape, historic farm fields, and the iconic covered bridges leading into the town square.
If you could only visit one town in all of Vermont, this should be the one.
11 Best Things to do in Woodstock
Covered Bridge Trio
There are three historic covered bridges within the town limits of Woodstock. All three allow passenger cars across. One has a pedestrian walkway making it easy to stop and marvel at the construction techniques used so long ago.
The Taftsville Covered Bridge is on the National Register of Historic Places. You can’t miss the long bright red bridge as you drive into town along Route 4. Spanning 189 feet across the Ottauqueechee River (pronounced AWT-ah-KWEE-chee), it’s among the oldest in the state and the nation, erected in 1836.
The Lincoln Covered Bridge is a single span of only 14 feet wide, located on the south end of town. Also crossing the Ottauqueechee River, the Lincoln Bridge’s construction took place in 1877 and stretches 136 feet across. This bridge is unique because it is the only known example of a wooded “Pratt Truss” bridge in the United States. It also appears on the National Register of Historic Places.
One of the most widely photographed covered bridges in Vermont stands just steps from the town green. The Middle Bridge on Union Street is not only beautiful but has perhaps the most unusual construction story. According to the Vermont Covered Bridge Society, the bridge was constructed near the current crossing site and pulled across the river into place by Ben and Jo, a team of oxen, in July of 1969. What a sight that must have been.
The bridges were not covered to protect those crossing them but rather to protect and preserve the bridge itself. Perhaps this is why so many still stand today.
Sleep at Woodstock’s Most Beautiful Address
Located in the heart of downtown Woodstock at #14 on The Green, is the luxurious Woodstock Inn and Resort. In classic New England style, the inn boasts Vermont craftsmanship at every turn allowing guests to immerse in timeless yet modern Vermont-style accommodations.
With 142 guest rooms and suites, the inn provides the perfect stepping-out point for year-round adventures, strolls through town, or a relaxing getaway. Inside guest areas include a classic library room with game tables for checkers and chess and a cozy pub-style gathering room with a wood-burning fireplace, pool tables, and tabletop shuffleboard.
A beckoning lobby, adorned with a stone fireplace, provides comfortable seating for reading or relaxing in the winter. Meticulously landscaped front and rear lawns provide seating areas under the shade of massive maples, the perfect spot to enjoy a summer cocktail.
Soothe Soak & Sun
Soothe away stress with a customized spa treatment at The Woodstock Spa. Located adjacent to the Woodstock Inn, the spa provides a respite from the ordinary. A two-story sunlight-filled lounging room allows guests to spend up to one hour in quiet relaxation before and after treatments. At the same time, the outdoor hot tub awaits just outside to relax away any lingering tension.
There are a total of ten private treatment rooms, along with steam rooms, saunas, and men’s and women’s locker room areas, complete with snacks and flavored water to enjoy in the lounging room. Total serenity!
Shops Boutiques & Stores
Unique local businesses housed in historic architecture welcome visitors year-round in Woodstock Village. Art galleries, bookstores, clothing, and specialty shops, along with cafes, restaurants, and bars, are all within walking distance as you set off to explore the village.
Whether you like to window shop or peruse inside, you’ll find Vermont originals such as the Vermont Flannel Company, the Clover Gift Shop, and F.H. Gillingham and Sons — Vermont’s oldest general store, operating since 1886. For the whimsical one in the family, check out Unicorn for unique gifts with a dash of sparkle.
Hike Mount Tom
Even if you don’t consider yourself a hiker, trust me when I say that climbing to the top of Mount Tom is worth the trek. Take the Faulkner Trail, a leisurely 45-minute walk through the woods on well-maintained and meandering switchbacks, allowing for an easy climb.
Once at the top, the reward is breathtakingly beautiful, with sweeping views over the town of Woodstock and nearby mountain ranges. There are convenient benches located in spots along the trail to aid your climb if a rest is needed. Wire handrails to hold onto appear just at the right place during the last push to the top, which is slightly more challenging.
Visit Sugarbush Farm
It’s no secret that Vermont is known for maple syrup and cheese, both of which you can sample here at Sugarbush Farm. A working 500-acre maple and dairy farm, Sugarbush is a great place for both kids and adults.
Step inside the farm store to sample over 15 varieties of cheeses and four distinct grades of maple syrup. At the same time, watch as cheesemakers painstakingly dip blocks of cheddar by hand into warm wax molds to preserve their freshness.
Outside, take a tour through the woods to see authentic maple tapping runs or get friendly with the resident goats and cows on the property. Then, stop by the self-tour barn to see a video on the process of making maple syrup, where a retired wood-fired boiler stands as a reminder of how daunting the boiling process is.
A President’s Home
President Calvin Coolidge State Historic Site – As if encapsulated in time, the birthplace and boyhood home of President Calvin Coolidge stands virtually unchanged and perfectly preserved, just as it looked in the early 20th century. Not only does the home of the 30th President of the United States of America remain furnished as it was in 1923, but the entire village is also painstakingly preserved.
You’ll find many exhibits: the general store, community church, a one-room schoolhouse, cheese factory, barns filled with antique tools and horse-drawn carriages, and a farm shop. They are just as they were when Coolidge was a boy. Take a guided tour, or walk the grounds on your own.
The Coolidge Museum and Education Center serves as the main entrance to the historic site. Several exhibits, an interactive multimedia room, and the museum store are worth the stop. Don’t forget to view the short film that tells how a boy from rural Vermont became President of the United States.
Billings Farm & Museum
A short scenic stroll from the village of Woodstock is an outdoor history museum you won’t want to miss. Regarded as one of the premier outdoor educational centers in the country, Billings Farm combines a working Vermont dairy farm with educational exhibits and interactive programs.
Tour farm-life exhibits, meet the Jersey herd, watch milking in progress, or visit the learning kitchen. In addition, you can participate in one or more activities and demonstrations on the farm each day.
Stop by the gift shop to pick up award-winning Billings Farm Cheddar, or head to the Dairy Bar for a scoop or two of Vermont-made ice cream. Visitors in the fall can sample cider donuts and hot mulled apple cider.
Walk Through History
Marsh-Billings-Rockefeller Historical Site – Three conservationist families, with lives spanning over 200 years, tell the story of one of Vermont’s most beautiful landscapes. The boyhood home of George Perkins Marsh, known as the father of American ecology, sits on over 550 acres of pasture and wooded mountain land.
Stroll through the meticulous gardens or take a walk in the woods under 400-year-old hemlocks along winding carriage roads to experience the beauty of nature. In addition, woodland enthusiasts can take part in hands-on workshops to learn how to manage and conserve the land.
National Park Ranger-led tours allow visitors to glimpse inside the stately Queen Anne-style mansion, later home to Frederick Billings, pioneer of reforestation and scientific farm management (and founder of Billings Farm). The entire estate, most recently used as a summer home by Mary and Laurance Rockefeller, was left as a gift to the visitors and residents of Vermont under one condition. It shall remain precisely how it appeared when they occupied the home, right down to the artwork on the walls.
Get Up Close & Personal at
The New England Falconry. Learn all about these amazing birds of prey from Chris Davis, a master falconer. Chris is also the first licensed falconry educator in the country. Experience handling and flying trained hawks while learning about adaptations necessary for raptors to survive. Chris also teaches about ongoing conservation efforts, essential to protect the species.
Introductory sessions (45 minutes) and extended sessions (90 minutes) are available for both participants and non-participants. A non-participant chooses not to handle the hawks but may otherwise fully participate in the educational session. For a full-on extended experience, choose the Eagle session (3 hours), where you’ll experience hawks, owls, and a bald eagle.
Farm-to-Table in Downtown Woodstock
Vermont may not have invented farm-to-table but dining out in downtown Woodstock might make you think that it had. Due to partnerships with several local farms, you’ll find fresh and seasonal options around almost every corner. Best of all, some of the downtown cafes and restaurants occupy historic buildings, allowing visitors a glimpse of Woodstock’s history.
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, the Mon Vert is a perfect spot to start your day. Serving breakfast options all day, you can grab a fancy cappuccino, a breakfast sandwich, or my favorite – the Lox and Schmear – smoked salmon and capers with cream cheese on an everything bagel. Lunch ranges from sandwiches to salads, with several grilled items and a kid’s menu. Specialty drinks, teas, beer, and wine are also available.
In what some refer to as the “Napa Valley of craft beer,” Worthy Kitchen puts heart and soul into local food and drink. With a commitment to making a difference in how they source food, Worthy Kitchen provides 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. We dined al fresco on the porch, enjoying the crispy fried brussels sprouts and the most decadent seafood stew steeped in a tomato fennel broth. Note the Tavern is only open daily from 5 p.m.—9 p.m.
Where to Stay in Woodstock
Looking for a place to stay in Woodstock? Check out these hotels located in Woodstock.
Booking.comIs Woodstock Worth a Visit?
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.
Everyone should experience the charm of Woodstock at least once in their lives. Unfortunately, historic towns like this seem to be fading with time. Still, the Woodstock village remains as vibrant and community-driven as it must have been in the 1800s.
Oozing with history and abundant outdoor activities, it’s a year-round destination worthy of a visit for the entire family. It also makes an exceptional destination for couples seeking a romantic getaway. It’s become my favorite Vermont destination, and I’ll bet it will be one of your favorites as well.
