10 Top Things to Do in Woodstock, Vermont

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. Jenne Farm, a family-owned business for more than 50 years, 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.

What people are drawn to is the picture-perfect iconic rural scenery—old red barn and outbuildings, rolling hills, trees that turn brilliant colors in the fall, and the reflecting pond.

Experience Rural Vermont Heritage

Billings Farm & Museum is a place to explore the evolution of agricultural practices in Vermont while also stepping behind the scenes of a commercial dairy operation. It's also a fun place for kids to experience farm life in interactive, hands-on ways.

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 butter churning.

Ski Suicide Six

The Woodstock Inn & Resort's Suicide Six ski area in South Pomfret has a storied past. The Suicide Six ski hill is known as the earliest ski resort. 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 beginners to experts.

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. Serious skiers staying in Woodstock will find big mountain thrills just 25 miles away at ​Killington Ski Resort.

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. The Marsh-Billings-Rockefeller National Historical Park was established in 1992 and opened to the public in 1998. It's 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, 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 outside of 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 some mustards, jams, and other items. Then you can 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 watch 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 4 miles east of the Village Green on Route 4. Vermont's third oldest covered bridge, which was originally built in 1836, had to be extensively restored following 2011's Tropical Storm Irene.

Hike Mount Tom

You can hike up Mount Tom from Woodstock. The 30-minute hike beginning on Mountain Avenue behind the covered bridge leads you up to a marvelous view of the town. You can snowshoe the trail in winter. Once up on top, you'll find more trails to extend your hike.

Shop Farmhouse Pottery

At Farmhouse Pottery you can not only purchase hand-made pottery and other home decor items, but you can also watch the potters at work during their open studio times. They also put on workshops where you can learn to make a pot on the potter's wheel. Founders, Zoe and James Zilian have been designing and crafting pottery and home decor items for over 10 years.

Enjoy a Farm to Table Meal

At Cloudland Farm in Pomfret, you can have a true farm-to-table experience. The restaurant is located on the Emmons family farm where much of the meat, produce and herbs are sourced. They serve their farm-to-table dinners on
Thursdays, Fridays, and Saturdays by reservation. While you are there, you can explore the farm, take photos of the animals and scenery and, before you leave, go shopping at their farm market for local meat, produce, and pottery.