Things To Do Americana at Its Most Charming

Named the number one small town in America by Conde Nast Traveler, Woodstock Village is true New England with its natural beauty and timeless charm. Explore miles and miles

of parkland, idyllic historical buildings, and plenty of shops, galleries, and eateries. Just one walk through the village is worth hours of enjoyment.

Shire ThingsToDo Cultural

Cultural AttractionsFor the Culturally Curious

From historic farms to renowned museums, Woodstock is home to a vibrant and celebrated culture for you to explore and experience.

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  • Middle Covered Bridge

    Mountain Ave, Woodstock, VT 05091

    • 0.5 miles
    • 11-minute walk

    Takes a walk over the Ottauquechee River, past some of Woodstock’s most beautiful homes, on Middle Bridge, one of the most-photographed covered bridges in New England.

    Billings Farm & Museum

    69 Old River Road, Woodstock, VT 05091

    • 0.9 miles
    • 15-minute walk

    Billings Farm and Museum offers a taste of traditional New England farm life circa 1890, with everything from butter-making to sheep-shearing demonstrations.

    Woodstock Farmers Market

    979 W Woodstock Rd, Woodstock, VT 05091

    • 1.7 miles
    • 5-minute drive

    Open Tuesday through Sunday, Woodstock’s premier whole foods market features produce, breads, meats, seafood, coffee, wine, microbrews, and more.

    Taftsville Covered Bridge

    Covered Bridge Rd, Woodstock, VT 05091

    • 3.0 miles
    • 6-minute drive

    Built in 1836 and overlooking the hydroelectric dam on the Ottauquechee River, this bridge is the second longest and third oldest bridge in Vermont.

man ready to ski in ski gear

Sports & Outdoor ActivitiesFor the Outdoor Enthusiast

Whether you prefer vigorous bike rides or refreshing dips in the river, you’re sure to appreciate Woodstock’s picture-perfect outdoor setting.

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  • Fly Fishing

    Anglers will certainly enjoy the many streams, rivers, and lakes available in this central Vermont location, offerings some of the best fly fishing in the nation.

    Learn More

    Alpine Skiing

    Killington is considered one of the best skiing destinations in the eastern U.S. With more than 1,500 skiable acres across six mountains, Killington offers varied terrain to suit skiers of all levels. Make sure to visit Killington during your stay with us.

    For more on Killington's 2020-2021 protocols, see here.

    Nordic Skiing

    If cross-country skiing is more your speed, the Tubbs Snowshoes and Nordic Adventure Center offers nearly twenty miles of groomed trails.


    From challenging mountain biking trails to great stretches of road, Vermont is home to great terrain for both casual riders and seasoned cyclists alike.


    Two of Woodstock’s three bridges offer access to swimming in the Ottauquechee River: the bridge at the end of Elm Street and the bridge adjacent to the Woodstock Recreation area.

    New England Falconry

    Visit the New England Falconry operation in Hadley, MA. Learn details about raptor adaptations, conservation, permitting and history of falconry, and experience free flying of the hawks.

Shire ThingsToDo ArtMuseums

Arts & MuseumsFor the Artists at Heart

We may be New England’s quintessential small town, but the town of Woodstock is flourishing with creativity and artistic spirit.

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  • Paul Revere Church Bell at First Congregational Church

    36 Elm St, Woodstock, VT 05091

    • 0.3 miles
    • 7-minute walk

    Woodstock is the only American town with five of the bells manufactured at the Massachusetts foundry once owned by Paul Revere. The earliest is on the porch of the Congregational Church.

    Woodstock Historical Society / Woodstock History Center

    26 Elm St, Woodstock, VT 05091

    • 0.4 miles
    • 8-minute walk

    The 1807 Dana House Museum displays 19th-century art, toys, furniture, tools, and more, while the History Center features an extensive research library and archive.

    Norman Williams Public Library

    10 The Green, Woodstock, VT 05091

    • 0.4 miles
    • 9-minute walk

    Built in 1883 by Dr. Edward Williams in loving memory of his parents, Norman and Mary, Woodstock’s beautiful red stone library occupies a central spot on the Green.

    Pentangle Arts Council

    31 The Green, Woodstock, VT 05091

    • 0.6 miles
    • 10-minute walk

    Experience first run films and state-of-the-art Dolby digital sound on the biggest screen in the Upper Valley at the old-fashioned Historic Town Hall Theatre and Pentangle.

    Green Mountain Perkins Academy Museum

    32 Academy Cir, South Woodstock, VT 05071

    • 5.4 miles
    • 10-minute drive

    From 1848–1898, Green Mountain Perkins Academy Museum was mainly a co-ed secondary boarding school. Today, this pristine structure and its many artifacts take you back 150 years.

Shire ThingsToDo Farming

Farming & AgricultureFor the Greenies

With nationally known dairy companies and, of course, our world-famous maple syrup, Vermont is a true leader in agriculture.

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  • Mount Tom Farmers’ Market

    979 W Woodstock Rd, Woodstock, VT 05091

    • 1.7 miles
    • 5-minute drive

    Featuring locally grown products and local artisans, the Mount Tom Farmers’ Market is located in the Mt. Tom parking lot, Rte. 12, just one half mile north of the village.

    Vermont Farmstead Cheese

    3786 Church Hill Rd, South Woodstock, VT 05071

    • 4.3 miles
    • 10-minute drive

    Vermont Farmstead Cheese produces artisanal old-world cheeses with Vermont quality, authenticity, and style. Visit their website for recipes, videos, and more.

    Kedron Sugar Makers

    4342 S Rd, South Woodstock, VT 05071

    • 4.8 miles
    • 10-minute drive

    Six generations of sugar makers at the same location, Kedron Sugar Makers is open daily in season, while maple syrup is available year round at the Kedron Valley Stables.

    Sugarbush Farm

    591 Sugarbush Farm Rd, Woodstock, VT 05091

    • 5.0 miles
    • 15-minute drive

    Sugarbush Farm features free tastings of cheese, maple syrup, and Vermont foods, as well as farm animals, a maple sugar house tour, and a nature walk.

    Cloudland Farm

    1101 Cloudland Rd, Woodstock, VT 05091

    • 5.3 miles
    • 15-minute drive

    Cloudland Farm’s store has natural Angus beef, prepared foods, and Vermont products. The restaurant offers enchanting farm-to-table dining with seasonal menus crafted by their chef.

Shire ThingsToDo Dining

DiningFor the Foodies

With an eclectic selection of wonderful local restaurants to choose from, Woodstock is an ideal destination for casual diners and foodies alike.

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  • Mon Vert Cafe

    28 Central St, Woodstock, VT 05091

    • 0.3 miles
    • 5-minute walk

    This French-inspired cafe, featuring sandwiches, salads, and pastries, is open daily for breakfast and lunch, with outside seating available during the summer.

    Mountain Creamery

    33 Central St #101, Woodstock, VT 05091

    • 0.3 miles
    • 7-minute walk

    Mountain Creamery offers a casual atmosphere with generous portions and traditional breakfast. Remember, credit cards not accepted.

    Village Butcher Shop

    18 Elm St #1, Woodstock, VT 05091

    • 0.4 miles
    • 8-minute walk

    Visit the Village Butcher Shop for to-go sandwiches and homemade donuts. Seating is available at outside tables or on the lawn of the Woodstock Historical society.

    Melaza Bistro

    71 Central St, Woodstock, VT 05091

    • 0.2 miles
    • 5-minute walk

    Caribbean Chef Diaz serves a menu inspired by his Puerto Rican roots at Melaza Bistro, a quaint eatery featuring a full bar.

    The Prince and the Pauper

    24 Elm Street, Woodstock, VT 05091

    • 0.4 miles
    • 7-minute walk

    Featuring classic American fare with an international flare, this long-running establishment offers an elegant yet subtle atmosphere. Reservations encouraged.

    Red Rooster and Richardson’s Tavern

    14 The Green, Woodstock, VT 05091

    • 0.7 miles
    • 10-minute walk

    Located in the Woodstock Inn, the Tavern provides a casual dining experience while the Red Rooster is formal with New American cuisine.

    Worthy Kitchen

    442 Woodstock Rd, Woodstock, VT 0509

    • 0.7 miles
    • 3-minute drive

    Offering fresh, farm-to-table meats and produce and an ample line of specialty beers, this rustic diner is open for drink and dinner daily.


    61 Central St, Woodstock, VT 05091

    • 0.3 miles
    • 5-minute walk

    Enjoy fresh, local fare at this intimate eatery, featuring an ever-changing menu of small plates and shared entrees, as well as a unique wine and beer list and house cocktails.

    The Daily Catch

    61 Central St, Woodstock, VT 05091

    • 0.3 miles
    • 5-minute walk

    From fried calamari to fresh linguine, New England’s finest seafood and pasta can be found at The Daily Catch, open evenings and weekends.

    Long Trail Brewing Co.

    5520 US-4, Bridgewater Corners, VT 05035

    • 8.7 miles
    • 14-minute drive

    Situated on the banks of the Ottauquechee River, this German-inspired brewery offers a rotating menu of locally sourced cuisine and a long list of handcrafted beer.

    Simon Pearce

    1760 Quechee Main St, Quechee, VT 05059

    • 6.5 miles
    • 11-minute drive

    An ideal way to experience Simon Pearce’s iconic, handmade glassware, The Mill at Simon Pearce serves creative American cuisine in a one-of-a-kind setting on the Ottauquechee River.

    Barnard Inn Restaurant & Max's Tavern

    5518 VT-12, Barnard, VT 05031

    • 9.7 miles
    • 14-minute drive

    Headed by award-winning chef Will Dodson, Barnard Inn offers freshly prepared, nightly dinner in one of the region’s most historic and elegant locations.