Local Eats • To Do & See + Shopping
Nestled in the heart of Vermont’s picturesque Green Mountains, Woodstock is a quintessential New England town brimming with charm and natural beauty. Known for its cobblestone streets, historic buildings, and vibrant arts scene, it’s the perfect destination for those seeking a peaceful getaway. Whether you’re exploring scenic trails, visiting world-class museums, or enjoying local shops and restaurants, Woodstock offers a delightful mix of outdoor adventure and small-town charm. Stay at The Shire Woodstock and immerse yourself in the serene beauty of this idyllic town, with the comfort and warmth of our inviting hotel just steps away from all the action.
Fueled by the Ottauquechee River–which rushes directly behind The Shire–Simon Pearce's turbine-powered glassblowing studio is a sight to see. Witness artisans crafting art in real time then dine at their award-winning farm-to-table restaurant.
1760 Quechee Main St, Quechee, VT 05059
Worthy Kitchen is the kind of no-fuss, order-at-the-bar spot that earned its cult following for good reason. Think farm-fresh burgers, fried chicken, and an ever-rotating tap list that would make any craft beer lover very happy. It's just a short drive from The Shire, but honestly, once you're settled in with a cold pint and a chalkboard full of good options, you won't be in any rush to leave. Photo Credit: Worthy Kitchen
442 Woodstock Rd, Woodstock, VT 05091
Woodstock is the kind of place that inspires art. The natural beauty, the quaint village, the Vermont sensibility, the slower way of life all contribute to a special feeling and we are excited to be part of the community.
We feature the work of local residents and owners Loren Fisher and Bob Wagner. The work on display is inspired by our travels throughout Vermont and around the world. Photo Credit: Focus Gallery
19 Central Street, Woodstock, VT 05091
Oakes & Evelyn brings its celebrated fine dining experience to the heart of Woodstock! Nestled at The Jackson, our newest location invites you to savor exquisite culinary creations. Start your day with a delightful breakfast, available daily. As evening descends, join us Tuesday through Saturday for an unforgettable dinner. Discover a destination where exceptional food and impeccable service create cherished moments.
43 Senior Lane , Woodstock, VT 05091
Experience the thrill of interacting with birds of prey in a stunning outdoor setting. Whether you're new to falconry or an experienced enthusiast, New England Falconry offers private, hands-on experiences to learn about these majestic birds and their training.
1044 Quechee Road, Pomfret, VT 05067
If you find yourself in Woodstock on a Thursday through Sunday morning, do yourself a favor and make the walk to the East End for Farmer and the Bell (the French crullers alone are worth the trip, with that light, custardy center and crisp shell that you just can't stop thinking about). It's the kind of place that started as a beloved pop-up and grew into something the whole area rallied around, and you can feel that love in every bite. Photo Credit: Farmer and the Bell
Every week from June to October, the Village Green transforms into the kind of farmers market that reminds you why small towns do it best, with local produce, handmade crafts, live music drifting through the air, and at its core it is authentically Vermont. When you visit Market on the Green Grab something fresh, wander the vendors, and let it stretch longer than you planned because it always does. Photo Credit: Woodstock Chamber of Commerce
The Grn, Woodstock, VT 05091
Mount Tom is a small peak, standing at 1357 feet, located in the town of Woodstock, Vermont. It is a part of the Marsh-Billings-Rockefeller National Historical Park.
A peaceful, scenic park perfect for a walk or a quiet picnic. Faulkner Park offers panoramic views of the surrounding countryside and a chance to unwind in nature, all while being just a short walk from downtown Woodstock.
74 Church Street, Woodstock, VT 05091
One of the largest ski resorts in the East, Killington Ski Area offers year-round outdoor activities. In the winter, it’s a mecca for skiing and snowboarding, while in summer, you can enjoy hiking, mountain biking, and stunning views.
4763 Killington Road, Killington, VT 05751
A working farm and museum that’s perfect for families. It offers interactive exhibits, live farm animals, and insights into Vermont’s agricultural history, making it a hands-on, educational experience for all ages.
69 Old River Road, Woodstock, VT 05091
Take a scenic walk along the Ottauquechee River or enjoy a peaceful kayaking or tubing adventure. The river offers beautiful views and is perfect for a leisurely afternoon, with the added bonus of being close to downtown Woodstock for easy access.
A beloved Vermont institution where you can tour a working sugarhouse, learn about maple syrup production, and sample their delicious cheeses. The farm is a great stop for food lovers wanting to take home local products.
591 Sugarbush Farm Road, Woodstock, VT 05091
A blend of natural beauty and conservation history, this park is home to miles of scenic trails through woodlands and gardens. The mansion offers tours about the Rockefeller family’s legacy in conservation, making it a unique spot for history buffs and nature lovers alike.
Located just outside the town, this working farm and museum showcases Vermont’s agricultural heritage. You can tour historic farm buildings, interact with livestock, and learn about traditional farming methods while enjoying stunning views of the surrounding countryside.
This beautiful park offers a mix of history and nature, with trails that wind through forests and past picturesque ponds. The mansion on the property, once home to the Rockefeller family, is a highlight, with tours that delve into the history of conservation in the U.S.
Woodstock’s downtown is a postcard-perfect blend of cobblestone streets, quaint shops, and cozy cafes. Take time to wander, enjoy the local boutiques, and perhaps grab a bite at one of the charming restaurants, such as the renowned Red Rooster.
