Woodstock, Vermont is a charming town where history, natural beauty, and small-town charm come together to create a truly unforgettable experience. Nestled in the heart of New England, this picturesque town and its surrounding area is a haven for nature lovers, history buffs, and those seeking a relaxing getaway. 

From its quaint streets lined with historic buildings to its breathtaking landscapes, Woodstock offers a plethora of must-see attractions that will captivate your senses and leave you wanting more. Whether you’re strolling along the covered bridges, exploring the vibrant local art scene, or indulging in farm-to-table cuisine, Woodstock has something for everyone. 

This guide will take a look at the top sights and activities that make Woodstock a destination you won’t want to miss. Get ready to fall in love with this enchanting town and create memories that will last a lifetime. 

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WOODSTOCK VERMONT TRAVEL GUIDE

History and Charm

Woodstock is steeped in history, and its charming atmosphere is evident as soon as you set foot in the town. Founded in 1761, Woodstock has managed to preserve its rich heritage through its well-preserved historic buildings and landmarks. Take a leisurely stroll down the town’s main street, lined with beautifully restored Federal-style houses and quaint shops. The Woodstock History Center, located in the heart of town, offers a fascinating glimpse into the town’s past with its collection of artifacts, photographs, and exhibits. From the colonial era to the present day, Woodstock’s history comes alive in this small but vibrant town. 

Woodstock is also known for its vibrant arts scene. The town is home to numerous galleries and studios showcasing the works of local artists. Art enthusiasts will enjoy exploring the various art forms on display, from traditional paintings to contemporary sculptures. The Woodstock Gallery, situated in a historic barn, is a must-visit for art lovers, featuring a diverse collection of works by local and regional artists. The town’s commitment to the arts is evident in its art festivals that showcase creativity that attracts visitors from near and far. 

Must-See Attractions

Woodstock offers a wide range of attractions that are sure to delight visitors of all ages and interests. One of the town’s most iconic landmarks is the Billings Farm & Museum, a working dairy farm that provides a glimpse into Vermont’s agricultural heritage. Explore the farm’s historic buildings, meet the farm animals, and learn about the farm’s sustainable practices. The adjacent Billings Mansion, a stunning 19th-century mansion, is open for tours and offers a fascinating look into the lives of its former residents. 

For nature lovers, Marsh-Billings-Rockefeller National Historical Park is a must-visit. This expansive park encompasses over 500 acres of forests, meadows, and trails, providing ample opportunities for hiking, picnicking, and wildlife spotting. Take a guided tour of the park’s historic mansion, once owned by the Rockefeller family, and learn about their commitment to conservation. The park’s serene landscapes and tranquil atmosphere make it the perfect escape from the hustle and bustle of daily life. 

Natural Beauty

Woodstock’s beauty extends beyond the borders of its town center. The surrounding area is filled with scenic landscapes, pristine rivers, and rolling hills, making it an outdoor enthusiast’s paradise. Lace up your hiking boots and embark on a journey along the Appalachian Trail, which passes through Woodstock. The trail offers breathtaking views of the Vermont countryside and is a favorite among hikers and nature lovers. 

If you prefer a more leisurely outdoor experience, head to one of the nearby parks or nature reserves. Quechee State Park, located just a short drive from Woodstock, is home to Quechee Gorge, often referred to as the “Grand Canyon of the East.” Marvel at the sheer cliffs and rushing waters of the Ottauquechee River as you hike along the gorge’s rim. The park also offers swimming, fishing, and camping facilities, allowing you to fully immerse yourself in the beauty of the outdoors. 

Covered Bridges

No visit to Woodstock is complete without exploring the town’s iconic covered bridges. These historic structures are a testament to the town’s rich heritage and offer a glimpse into a bygone era. The Taftsville Covered Bridge, located just outside of town, is one of the oldest covered bridges in Vermont and is a popular spot for photographers. Drive or walk across the bridge, taking in the views of the Ottauquechee River below. 

Another must-see covered bridge is the Middle Covered Bridge, located downtown on River Road. This picturesque bridge that is a dark wood on one side and a light gray on the other is also a favorite subject for painters and photographers. Take a leisurely stroll across the bridge and enjoy the peaceful surroundings, listening to the sound of the river flowing beneath you. 

The Quechee Covered Bridge located just outside Woodstock and the entrance to the sleepy little town of Quechee and the Lincoln Covered Bridge located west of Woodstock and listed on the National Register of Historic Places are two others that you should not miss. The covered bridges of Woodstock are not only historic landmarks but also serve as a reminder of the town’s timeless charm.

Farms and Tastings

Woodstock’s agricultural roots are still very much alive today, with numerous farms and orchards dotting the surrounding countryside. Take a scenic drive through the rolling hills and discover the bounty of the land. Visit a local farm and learn about sustainable farming practices, pick your own fruits and vegetables, or simply enjoy the fresh country air. 

If you’re a food lover, Woodstock offers a variety of farm-to-table dining options. Indulge in a delicious meal prepared with locally sourced ingredients at one of the town’s many restaurants. The Lincoln Inn & Restaurant, situated in a historic farmhouse, is known for its innovative farm-to-table cuisine and warm hospitality. Savor the flavors of Vermont as you dine in a charming setting, surrounded by the beauty of the countryside. 

You cannot leave Woodstock with tasting its pure maple syrup! It is delicious and is not the maple syrup you find in a grocery store! A few farms offer tastings and tours including Sugarbush Farm and Bourdon Maple Farm.  The cheeses at Sugarbush Farms are amazing too!

Two other farms that you have to see just to get a photo are Sleepy Hollow Farm and Jenne Farm, especially if you visit during the Fall.  My photo of Sleepy Hollow Farm, shown above, was taken in June.  While still very pretty, Fall is when it is really unbelievably gorgeous.

Shops and Galleries

Woodstock is a shopper’s paradise, with its quaint streets lined with unique boutiques, art galleries, and specialty shops. Explore the town’s eclectic mix of stores and discover one-of-a-kind treasures. From handmade crafts to antique furniture, there’s something for every taste and budget. 

One of the must-visit shops in Woodstock is the F.H. Gillingham & Sons General Store, a family-owned store that has been operating since 1886. Step back in time as you browse the shelves stocked with gourmet foods, Vermont-made products, and nostalgic toys. The store’s old-world charm and friendly staff make it a delightful place to explore and find souvenirs to take home. 

Dining

Where to Stay

Woodstock offers a range of accommodations to suit every traveler’s needs and preferences. From charming bed and breakfasts to luxurious resorts, you’ll find the perfect place to rest and rejuvenate after a day of exploring. 

The Woodstock Inn & Resort, pictured above, is located in the heart of town and is a popular choice for those seeking a luxurious stay. This historic resort offers elegantly appointed rooms, a full-service spa, and a golf course, ensuring a truly indulgent experience. If you prefer a more intimate setting, consider staying at one of the town’s bed and breakfasts, such as the Ardmore Inn. These cozy establishments offer personalized service and a warm, inviting atmosphere, making you feel right at home. 

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Transportation

To see these places you will need a car.  Parking is easy in each place.

You can rent a car at any of the nearby airports.  Several airports will get you within a couple hours drive of Woodstock, including Lebanon (LEB), Albany (ALB), Manchester (MHT), Boston (BOS), Portland (PWM), and Burlington (BTV).

Currency

The national currency in the United States is the US Dollar ($).  Click here to get the daily conversion.