How to Spend a Perfect Weekend in Woodstock, Vermont
Arriving in Woodstock, Vermont, you’d be forgiven for thinking you had made a wrong turn and ended up on the set of Gilmore Girls. Like the show’s Stars Hollow, Woodstock has quaintness in abundance. Off Central Street (there are no stop lights here or anywhere in town for that matter) a bulletin board dubbed “Woodstock Town Crier” lists the goings on of the week. On the village green, flyers advertise a Strawberry Supper a local church, a celebration of cheese and dairy at Woodstock’s Billings Farm & Museum, and the upcoming summer stock performance at the Town Hall Theatre. Streets are populated with well curated, locally owned shops, covered bridges take bicyclers across babbling rivers, and there is Vermont-made cheese, maple syrup, and craft beer at every turn. Pair this bucolic charm with a host of unique activities and the outstanding natural beauty of the Green Mountains, and it’s easy to see why Woodstock is considered one of the prettiest small towns in the country. Here's how to spend the perfect weekend in Woodstock, Vermont.
Woodstock Inn & Resort
It’s tempting to spend the entire weekend on the grounds of the Woodstock Inn & Resort, a horseshoe-shaped colonial lodge in the heart of the village built by John D. Rockefeller’s grandson Laurance. Two grand lawns feature shaded Adirondack chairs perfect for whiling away the afternoon with a book, while a heated outdoor pool with cocktail service offers a decidedly luxurious way to beat the heat. Visit the LEED-certified spa for full-body massages using products sourced from local vendors and inspired by the season and an fireside whirlpool outdoors to keep the relaxation going post-treatment. All of the hotel’s recently renovated guest rooms feature furniture handmade by local craftsmen and wood-burning fireplaces. To make the most of the summer light, opt for a Tavern Porch room, which includes a glass-enclosed sunroom. When you are ready to venture out, hop on one of the complimentary bikes to explore town on two wheels, or take a short drive to the Resort’s Woodstock Athletic Club for yoga and fitness classes, outdoor trails, and tennis.
Mont Vert Cafe
Start the day with a latte infused with local maple syrup at this popular coffee shop serving organic fare on Central Street. Don’t miss the fresh biscuits and gravy with house made sausage for breakfast or, for lunch, the “Devils on Horseback” panini with homemade date-walnut spread, local bacon, and goat cheese.
Open for breakfast, lunch, and dinner, this New American at Woodstock Inn & Resort is the town’s special occasion spot thanks to an upscale menu built around staples of the Northeast, a pretty, light-filled dining room with a shaded outdoor porch, and excellent service. Arrive early for a pre-dinner cocktail in the Adirondack chairs beneath the giant pin oaks on the Inn’s front yard.
Ask anyone in town about their favorite restaurant, and this “farm diner” on Woodstock’s east end will be at the top of the list. Fans keep coming back for comforting staples like the buttermilk fried chicken and the mac n cheese made with roasted garlic cream and aged local cheddar, paired with a pint from the extensive brewed-in-Vermont craft beer and cider list.
Thursday through Saturday, Chef Ira White leads a true farm-to-table dinner experience using ingredients grown right outside the post-and-beam dining room’s door to create a three-course prix-fixe menu. BYOB wine from local general store F. H. Gillingham & Sons, which recommends pairings based on the Cloudland menu each night.
The Village Butcher
While this longtime butcher still sells prime cuts, it’s the baked goods that make this Elm Street shop worth a stop. Their baker, Mary, has been with the store for 25 years whipping up lemon squares, brownies, and cinnamon rolls. The store also sells a selection of frozen meat pies including a wildly popular pork version made by butcher and owner George Racicot from a recipe handed down from his French ancestors.
Locals and visitors alike end the day with well-mixed cocktails at this cozy tavern. Curl up in a club chair by the fireplace and say “yes” to the dessert menu, which includes Vermont maple cake and a selection of local cheeses.
Woodstock Farmer’s Market
Food lovers will have a ball browsing the shelves of this farmer’s market chock full of locally made products from jam to ice cream to pancake mix. The cheese selection is equally bountiful as is the deli’s menu of sandwiches, which can be enjoyed at picnic tables overlooking the Ottauquechee River.
Vermont’s oldest continuously operated independent bookshop has become a destination for book lovers who appreciate the expertly curated shelves that include an extensive selection of works by local writers and books dedicated to the history and natural beauty of Vermont. Shoppers will also find an assortment of greeting cards, stationery, and vinyl.
F.H. Gillingham & Sons
Family owned and operated since 1886, this Elm Street general store has 8,000-square-feet of gift-ready merchandise—Vermont maple syrup, local maple cookies, and their own collection of cheese—plus lots of delightful non-essentials, too (Will Moses folk art puzzles, anyone?)
Housed in a former bible bindery, Farmhouse Pottery’s Zoe and James Zilian create attractive and functional wheel-thrown pottery pieces for the table. They offer personal pottery lessons and wheel workshops, like the Couples Clay Date Night with wine and cheese, in their studio.
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SEE & DO
Billings Farm & Museum
This working dairy farm is a treat for animal lovers, who can meet the Jersey cows, draft horses, sheep, and goats that call it home. It’s also a museum dedicated to preserving Vermont’s rural heritage and includes the restored 1890 farmhouse visitors can tour for a glimpse of agricultural life at the turn of the 19th century. Check their calendar for unique events throughout the year including a baby farm animal celebration, juried quilt exhibition, and a party for National Ice Cream Day.
Marsh-Billings-Rockefeller National Historical Park
Just across the street from Billings Farm & Museum is the Marsh-Billings-Rockefeller National Historical Park, named for three of Woodstock’s most prominent conservationists. The 555 acres of forest include over 20 miles of shaded woodland trails, century-old carriage roads, and Vermont’s first tree farm. For the best views in town, hike Mount Tom’s south peak, which offers a panorama of the village and the surrounding mountains.
New England Falconry
Try your hand at the ancient sport of kings during a lesson at New England Falconry located in Woodstock’s historic Rutherford Barn. Master falconer Chris Davis, who has served as an instructor since 1985, or a member of staff leads the 45-minute introductory flying session with a trained Harris’s Hawk in the center’s meadow.
Kelly Way Gardens
This three-acre garden nestled on the hillside of the Kedron Valley has provided farm-to-table vegetables, fruits, herbs, and flowers to the Woodstock Inn & Resort since 2013. This spring saw the opening of Red Barns at Kelly Way Gardens, a restored 19th century venue that hosts cooking classes and dining events throughout the year. Plan a trip to coincide with their Red Barn Dinner Series on Sundays in July and August, with meals created from the state’s finest cheese makers, farmers, beekeepers, and dairymen, as well as just-picked ingredients from Kelly Way. Tours and tastings, as well as afternoon tea in the garden, are ongoing throughout the summer.
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