10 Top Things to Do in Woodstock, Vermont

Hike to the Top of Mount Tom

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).

Celebrate All Things Calvin Coolidge

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.

Visit New England's Most Photographed Farm

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

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

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

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

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, 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

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

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.