Things To Do
Hiking
(Spiciness Level: * = Easiest, -> *** = Most Challenging) • Mt. Peg Trail (*) — A lovely, gentle loop through the woods right from the village, with pretty views over Woodstock. Perfect for a relaxed morning walk or an easy afternoon outing. • Woodstock Faulkner Trail / Mt. Tom (**) — This beloved local hike climbs through switchbacks up to the top of Mt. Tom, rewarding you with sweeping views over the village and the surrounding Green Mountains. The lower loop along the river is beautiful on its own, too. • Saskadena Six (**) — A moderate hike on the ski mountain's trails, offering scenic views of the upper valley and a real taste of Vermont's forested hills. • Killington E-Trail (***) — For those looking to push themselves, this challenging trail delivers big views and a serious workout. Not for the faint of heart, but absolutely worth it if you're up for it.
Woodstock Inn Country Club & Athletic Center
A classic Vermont golf course with a beautiful setting. Challenging enough to keep it interesting, scenic enough to make it worth it even if your game isn't perfect. Woodstock Inn Athletic Center: Guests of the area have access to a great athletic center with tennis courts, a pool and sauna, and a full gym — ideal for getting moving before a day of exploring or winding down after one.
Mountain Biking
Woodstock punches well above its weight for mountain biking. There's something for everyone: • Mt. Peg Trails — Cross-country riding right in the village, accessible and fun. • Saskadena Six — Offers both downhill and XC trails, with terrain for all skill levels. • Aqueduct Trails — A beloved local XC network, great for a fast-moving adventure through the trees.
Billings Farm & Museum
Just a half-mile walk from the village green, Billings Farm is one of the finest outdoor history museums in the country — and also a fully operating Jersey dairy farm. Originally developed in 1871 by Frederick Billings as a model of sustainable agriculture, the farm has been part of Woodstock's landscape for over 150 years. Wander through the beautifully restored 1890 farmhouse, meet the Jersey cows, draft horses, sheep, and chickens, sample raw-milk cheddar from the dairy, and catch the afternoon milking at 3:30. In summer there's an heirloom garden and ice cream terrace; in winter, horse-drawn sleigh rides through the snowy fields. A genuinely magical place, no matter the season.
Farmhouse Pottery
Farmhouse Pottery is a working studio and retail shop where every piece is wheel-thrown by hand using old-world techniques. Founded by husband-and-wife duo Zoe and James Zilian, the shop blends a modern farmhouse aesthetic with a deep commitment to craft and community. Whether you're picking up a handmade mug, a beautiful serving bowl, or booking a wheel-throwing workshop for a memorable hands-on experience, Farmhouse Pottery is worth every minute.
Simon Pearce
Just a short drive from Woodstock in neighboring Quechee, Simon Pearce is an icon of Vermont craftsmanship. Perched atop the falls of the Ottauquechee River — powered by its very own hydroelectric turbine — the flagship mill is home to a working glassblowing studio where you can watch master artisans shape molten glass by hand. Browse the stunning showroom for handcrafted glassware and pottery, then linger at the award-winning restaurant overlooking the waterfall and covered bridge.
Mashu Vintage
For anyone who loves a good treasure hunt, Mashu is the spot. This carefully curated vintage and thrift shop brings a fresh, fashion-forward eye to secondhand clothing — think of it as the opposite of digging through bins. Great for a browse whenever the mood strikes.
Mon Vert Cafe
This French-inspired organic cafe in the center of the village is something close to Woodstock's living room. The entire menu is built on locally sourced and organic ingredients — think hearty breakfast burritos, fresh sandwiches on Red Hen Bakery bread, rich coffee drinks made with Strafford Organic milk, and homemade pastries baked fresh daily. It's a first-come, first-served spot with a warm, eclectic vibe. Arrive a little early on weekends — it fills up fast, and for very good reason.
Abracadabra Coffee Co.
Woodstock's most charming caffeine stop is served out of a vintage 1964 Shasta trailer. Abracadabra pours excellent specialty coffee alongside house-made waffles and seasonal creemees, all with a cozy, cheerful energy that perfectly captures the spirit of this town. Best cold brew in the Upper Valley according to Sam.
Village Butcher Shop
A Woodstock institution. Stop in for a made-to-order sandwich stuffed with high-quality local ingredients — simple, satisfying, and perfect for fueling up before a hike or picnic on the green.
Au Comptoir
Sam's favorite spot for a negroni, tin fish, and potato chips. Tucked down a brick alley near the Woodstock Welcome Center, Au Comptoir — French for "at the bar" — is a Parisian-inspired craft cocktail bar from Zoe Zilian, co-founder of Farmhouse Pottery. The space is stunning: wood, stucco, and marble details with jazz playing softly in the background. The cocktail menu changes seasonally and is full of creative, thoughtfully crafted drinks made with the freshest ingredients. Small bites, organic wines, and a genuinely wonderful atmosphere round out the experience. This is where you go for a perfect evening drink.
Worthy Kitchen
A local institution just east of the village, Worthy Kitchen is the definition of farm-to-table done right, without any fuss. Think elevated pub food — excellent fried chicken, creative burgers, wings, nachos — paired with a massive and carefully curated list of local draft beers. The vibe is casual, lively, and welcoming, and it's genuinely where the locals eat. A perfect spot for a group dinner.
Ranch Camp Woodstock
Part mountain bike shop, part laid-back cantina & outdoor bar. The menu leans Mexican-inspired: hearty burritos, tacos, bowls, and burgers, all made with fresh local ingredients and a Vermont twist (maple roja sauce is real, and it's delicious). Excellent options for vegetarian, vegan, and gluten-free diners. Walk-ins welcome, no reservations needed.
The Ransom Tavern
Set inside the historic Kedron Valley Inn in South Woodstock — a short scenic drive from the village — Ransom Tavern is a deeply charming dinner destination. The menu celebrates the Neapolitan pizza tradition with beautifully crafted wood-fired pies, antipasti, and fresh salads, all served in a cozy, candlelit dining room or at the vintage-inspired bar. A solid cocktail list, local beers, and a convivial atmosphere make this one of the most enjoyable evenings you can have in the Woodstock area. Reservations are encouraged.
Santé
Santé is a small, intimate restaurant on Central Street with a menu that changes seasonally and showcases locally harvested meats, fish, and produce. The food is inventive and precise — think freshly made pasta, beautifully cooked fish, creative small plates — paired with excellent hand-crafted cocktails and a thoughtful wine list. The atmosphere is lively but refined, making it ideal for a special night out or a romantic dinner. Reservations are a must, especially on weekends.
Long Trail Brewing Company
About a 10-minute drive from the village in Bridgewater, Long Trail Brewing is one of Vermont's most iconic craft breweries. The taproom sits right on the Ottauquechee River, with a solid pub food menu and a rotating selection of their well-loved ales and seasonal brews. A great stop after a day on the trails.