Top 20 Things to See in Woodstock VT: A Tourist’s Guide to Must-Visit Spots

Nestled in the heart of New England, Woodstock, VT, is often hailed as the prettiest town in America. This picturesque village is a perfect blend of charming architecture, breathtaking natural scenery, and a vibrant community spirit. Whether you’re strolling through the historic village green, savoring a cup of coffee at a local café, or taking in the views from the iconic covered bridge, Woodstock offers an enchanting experience that feels like stepping into a storybook.

For those who love history and culture, Woodstock is a treasure trove. Explore the beautifully preserved Calvin Coolidge Homestead District, visit the Woodstock Historical Society, and step back in time at Gillingham’s, the town’s oldest general store. The town’s weekly Market on the Green and the renowned Farmers Market provide an authentic taste of local life, offering fresh produce, handmade crafts, and delightful culinary treats.

Outdoor enthusiasts will find plenty to love in Woodstock as well. From skiing and mountain biking at Saskadena Six to hiking up Mt. Tom for stunning panoramic views, there are activities for every season. Add to this the charm of farm-to-table dining at Cloudland Farm, the creativity on display at Farmhouse Pottery, and the inviting atmosphere of local eateries and shops, and you have a destination that’s as diverse as it is delightful. Woodstock, VT, is a place where every corner holds a new adventure, making it a must-visit for travelers seeking both relaxation and excitement.

Morning Village Walk

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The Village Green

My day began with a leisurely stroll through the village green, the heart of Woodstock. The green is surrounded by beautifully preserved historic buildings that exude New England charm. Walking through this area felt like stepping back in time, with the town’s architecture reflecting its storied past.

Mon Vert Cafe

No morning walk is complete without a good cup of coffee. I stopped by Mon Vert Cafe, a cozy spot known for its delicious cappuccinos and welcoming atmosphere. Sipping my coffee while watching the world go by was the perfect way to start the day.

Covered Bridge

A short walk from the village green led me to the iconic Middle Covered Bridge. This beautiful structure spans the Ottauquechee River and offers breathtaking views of the surrounding scenery. Standing in the center of the bridge, I took a moment to appreciate the tranquility and beauty of Vermont.

Breakfast Delights

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Eggs & Pancakes at The Creamery

For breakfast, I headed to The Creamery. Though it’s not a fancy place, the food is absolutely delicious. I indulged in their eggs and pancakes, which were cooked to perfection. The Creamery’s rustic charm and hearty breakfast made for a memorable meal.

Artistic Inspirations

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Farmhouse Pottery

Next on my itinerary was a visit to Farmhouse Pottery. Located in an old bible binding building, this studio creates beautiful and functional pottery. Watching the artisans at work was inspiring, and I couldn’t resist purchasing a piece as a souvenir. The craftsmanship and dedication to tradition here are truly impressive.

Outdoor Adventures

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Saskadena Six Ski Area & Bike Park

Woodstock’s very own ski area, Saskadena Six, offers a fantastic mix of activities. In the winter, it’s a haven for skiers and snowboarders of all abilities. The easy-riding terrain is perfect for families and beginners. In the summer, the bike park comes alive with downhill tracks and a skills area. I had a blast shredding the trails on a mountain bike and even tried a few new tricks.

Teago General Store

On my way to Saskadena Six, I stopped by the Teago General Store. This charming store offers great sandwiches, hot chocolate, and a taste of local life. It’s a perfect spot to grab a bite and soak in the community’s vibe.

Culinary and Market Experiences

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The Farmers Market

Adjacent to the 506 On The River Inn, the Farmers Market is a must-visit. It’s world-class, offering a wonderful selection of sandwiches, prepared foods, and baked goods. I sampled some of Vermont’s best cheeses and picked up a few treats to enjoy later.

Billings Farm and Museum

A visit to Billings Farm and Museum provided a delightful glimpse into Vermont’s agricultural heritage. This working farm offers wagon rides, cow feeding sessions, and interactive exhibits that are especially fun for kids. Learning about the history and practices of farming in Vermont was both educational and entertaining.

Weekly Markets and Historic Sites

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Market on the Green

Every Wednesday, the Market on the Green transforms the village green into a bustling marketplace. Fresh produce, prepared foods, crafts, and live music create a vibrant atmosphere. It’s a great place to mingle with locals and experience the community spirit.

Sugarbush Farm

At Sugarbush Farm, I got to sample a variety of cheeses and learn about the maple syrup-making process. This thriving farm is a living testament to Vermont’s agricultural traditions. The scenic surroundings and hands-on experiences made it a highlight of my trip.

Calvin Coolidge Homestead District

A short drive from Woodstock brought me to the Calvin Coolidge Homestead District. This historic site is the birthplace and boyhood home of Calvin Coolidge, the 30th President of the United States. Walking through the well-preserved buildings and learning about Coolidge’s life and presidency was fascinating.

Shopping and Historic Architecture

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Gillingham’s is Woodstock’s oldest store, operating since 1858. Stepping inside felt like a journey back in time. This authentic general store offers a mix of modern products and Vermont crafts. It’s a great place to find unique gifts and souvenirs.

Historic Park

Exploring the Historic Park allowed me to admire the architecture and grounds of a beautifully preserved mansion. The intricate details and grandeur of the building were captivating. It’s a serene spot to take a leisurely walk and soak in the town’s history.

Local Eats and Creative Havens

The Village Butcher

The Village Butcher

For lunch, I grabbed a sandwich from The Village Butcher. Their extensive back lawn, open to the public, offers beautiful views of the Ottauquechee River. Enjoying my meal with such a picturesque backdrop was a treat.

Simon Pearce

A short drive from Woodstock led me to Simon Pearce, a haven of creativity. This glassblowing studio and retail store also houses a fantastic restaurant overlooking the stunning Quechee covered bridge and waterfall. Watching the glassblowers at work and dining with such a view was a truly memorable experience.

Long Trail Brewery

Following the trail to the Long Trail Brewery was another highlight. This renowned brewery offers a range of delicious brews. I enjoyed sampling different beers and dining in their casual, lively restaurant on the banks of the Ottauquechee River.

Farm-to-Table Dining and Scenic Hikes

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Cloudland Farm

For dinner, I headed to Cloudland Farm. This farm-to-table restaurant offers a magical dining experience. Advance bookings are required, and it’s worth planning ahead. The farm-raised dinner in such a picturesque setting was one of the best meals I’ve had.

Mt. Tom

To work off all the delicious food, I embarked on a hike up Mt. Tom. The 30-45 minute hike to the top is moderately challenging, but the views of Woodstock Village from the summit are breathtaking. I packed a lunch and enjoyed a picnic with a view.

Historical Insights and Community Events

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Woodstock Historical Society

The Woodstock Historical Society is a must-visit for history enthusiasts. The museum offers a unique insight into the history of Woodstock and the surrounding area. Exhibits include stories and photos of the town’s creation and the lives of famous and not-so-famous residents.

Town Supper

One of the most charming experiences was attending a town supper. These community meals are organized in various granges and town halls across the state. They offer delicious home-cooked food and a wonderful sense of community. It’s a unique way to connect with locals and experience Vermont’s hospitality.

Scenic Rides and Recreational Activities

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Barnard Lake

A visit to Barnard Lake was perfect for a relaxing swim and a picnic lunch from the Barnard Store. The scenic beauty and tranquil waters make it a great spot to unwind. For those who enjoy cycling, the ride on the Stage Road back to Woodstock is splendid.

Woodstock Country Club

Rounding off my trip, I spent some time at the Woodstock Country Club. This Robert Trent Jones-designed course offers a challenging round of golf. In the winter, the club transforms into a cross-country ski destination, providing outdoor fun year-round.


Woodstock, VT, is a treasure trove of experiences. From scenic walks and historic sites to vibrant markets and delicious food, the town offers something for everyone. Whether you’re an outdoor enthusiast, history buff, or foodie, Woodstock’s charm and hospitality will leave you with lasting memories. I can’t wait to return and explore even more of this beautiful New England village.