10 Amazing Things to Do in Woodstock Vermont Plus Hidden Gems
Tucked away in the heart of the Green Mountains, Woodstock, Vermont is one of New England’s most charming small towns,where covered bridges, rolling farmland, and historic charm meet mountain adventure. Whether you’re visiting for fall foliage, a cozy winter getaway, or a summer countryside escape, Woodstock delivers that postcard-perfect Vermont experience year-round. This guide highlights the 10 amazing things to do in Woodstock Vermont, along with hidden gems, where to stay, and essential tips for first-time visitors.
Overview
Founded in the 1700s, Woodstock is known as “the prettiest small town in America” for good reason. The downtown village is filled with Federal-style architecture, local art galleries, farm-to-table restaurants, and boutique shops. Surrounding it are scenic hills, working farms, and hiking trails that reveal Vermont’s timeless beauty.
From exploring the Marsh-Billings-Rockefeller National Historical Park to sampling cheese at Billings Farm, or strolling over the Middle Covered Bridge, Woodstock offers the perfect mix of relaxation and outdoor fun in every season.
10 Best Things to Do in Woodstock Vermont
1. Explore Marsh-Billings-Rockefeller National Historical Park
This park blends natural beauty with fascinating history. You can tour the grand Rockefeller mansion, explore forested hiking trails, and learn about conservation efforts that shaped America’s environmental movement. The carriage roads are ideal for walking or snowshoeing in winter.
2. Visit Billings Farm and Museum
An authentic working dairy farm and museum, Billings Farm is one of Woodstock’s most popular attractions. Watch cows being milked, meet friendly farm animals, and learn about Vermont’s agricultural past. In autumn, the farm glows with colorful foliage and seasonal events like harvest festivals.
3. Stroll Across the Middle Covered Bridge
Built in 1969 but modeled after 19th-century designs, the Middle Covered Bridge is the most photographed spot in Woodstock and one of the most popular covered bridges in Vermont. It spans the Ottauquechee River and connects the village to the countryside, perfect for sunset walks or photo sessions.
4. Discover Downtown Woodstock
Downtown Woodstock is lined with boutiques, art galleries, cafés, and bookstores. Stop by FH Gillingham & Sons, a general store operating since 1886, for local maple syrup, cheese, and Vermont-made gifts. Don’t miss a latte from Mon Vert Café—a local favorite.
5. Hike Mount Tom
For panoramic views of the village and surrounding hills, hike the Mount Tom Trail located inside Marsh-Billings-Rockefeller Park. The trail is moderately challenging but rewards hikers with sweeping vistas, especially during fall foliage.
6. Visit Quechee Gorge
Just a short drive from Woodstock, Quechee Gorge, known as “Vermont’s Little Grand Canyon”—offers breathtaking views of the Ottauquechee River cutting through steep cliffs. A scenic bridge overlooks the gorge, and nearby trails lead down to the water’s edge.
7. Tour Sugarbush Farm
A family-run maple syrup and cheese farm, Sugarbush Farm invites visitors to learn about the maple sugaring process and taste pure Vermont syrups. The scenic drive up the hill offers stunning countryside views—especially in autumn.
8. Relax at The Spa at Woodstock Inn
The Woodstock Inn & Resort isn’t just a charming place to stay—it’s home to a luxurious spa that focuses on wellness and relaxation. Unwind with a massage, soak in a hot tub, or simply enjoy the peaceful mountain setting.
9. Take a Scenic Drive on Route 4
Route 4 is one of Vermont’s most beautiful byways. From Woodstock, you can head west toward Killington or east toward Quechee, passing covered bridges, farm fields, and forested valleys along the way. It’s especially stunning during peak foliage.
10. Visit the Taftsville Covered Bridge
One of Vermont’s oldest covered bridges, Taftsville Bridge dates back to 1836. Painted in bright red, it sits just east of town and offers a perfect photo opportunity, especially when reflected in the river below.
Hidden Gems
- Faulkner Park Trail: A quiet hiking trail less crowded than Mount Tom, leading to beautiful views of the valley.
- Ottauquechee River Trail: An easy riverside path starting near the East End Park—great for morning walks.
- Farmhouse Pottery: A local artisan studio where you can watch pottery being made and even join a workshop.
- Long Trail Brewery (Bridgewater Corners): Just 15 minutes away, this riverside brewery serves craft beers and hearty Vermont fare.
- Silver Lake State Park: A short drive north in Barnard, this small lake is perfect for swimming, kayaking, or picnicking on summer afternoons.
Best Times to Visit
- Fall (September–October): The best time to experience vibrant foliage and crisp mountain air.
- Winter (December–February): Ideal for skiing, snowshoeing, and cozying up by the fireplace.
- Spring (April–May): Watch maple sugaring season and the countryside come back to life.
- Summer (June–August): Great for hiking, swimming, and exploring the farmers’ markets and festivals.
Where to Stay
Check Woodstock Vermont hotels
First-Time Visitor Tips
- Book early during fall: Accommodations fill up quickly in foliage season.
- Bring cash: Some local farms and markets are cash-only.
- Walk the village: Parking is limited—walking is the best way to explore downtown.
- Visit early morning: Popular attractions like Billings Farm are quieter before 10 AM.
- Pack layers: Vermont weather changes quickly—be prepared for warm days and cool evenings.
Packing List
- Comfortable walking shoes or hiking boots
- Warm jacket or fleece (even in summer nights)
- Camera for covered bridges and landscapes
- Reusable water bottle
- Map or offline GPS for countryside drives
- Swimsuit (for summer lake visits)
- Travel-sized umbrella or raincoat
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Final Thoughts
Woodstock, Vermont is the essence of New England charm, a town where time slows down and nature takes center stage. Whether you’re hiking Mount Tom, tasting maple syrup at Sugarbush Farm, or simply admiring the village’s covered bridges, you’ll find serenity in every corner. Each season brings new beauty, making Woodstock a destination worth revisiting again and again.
If you’re planning your first trip, start with these 10 amazing things to do in Woodstock Vermont and you’ll discover why so many travelers fall in love with this enchanting village in the Green Mountains.
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