13 Best Things to Do in Woodstock, Vermont
Woodstock is exactly how you imagine a small New England town in the fall. We visited Woodstock during our New England fall road trip, and it quickly became one of our favorite stops in Vermont!
The village itself is compact and easy to explore on foot, but some of the area’s best attractions are tucked away in the surrounding countryside.
From wandering around The Green and visiting Billings Farm to sampling maple syrup at Sugarbush Farm and exploring nearby Quechee Gorge, there is plenty to fill your itinerary. In this guide, I’ll show you the best things to do in Woodstock, Vermont, along with practical tips to help you plan your visit.
Disclosure: This post contains a few affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through my link.
Quick Travel Planning Tips for Woodstock, Vermont
🏨 Where to Stay: Stay close to the center of Woodstock so you can easily walk to the village’s shops, cafés, and restaurants. The Shire Woodstock is a charming option right by the river, while On the River Inn offers more facilities in a peaceful setting just outside the village. Book well in advance, as accommodation fills up quickly during fall foliage season!
✈️ How to Get There: Woodstock is easiest to reach by car. Burlington Airport is around 1.5 hours away, while Boston Logan Airport is approximately a 2.5-hour drive.
🚗 How to Get Around: Downtown Woodstock is compact and easy to explore on foot, but you’ll need a car to visit attractions outside the village (and to get there in the first place). I recommend using Discover Cars to compare prices and find the best rental-car deal.
🍁 When to Visit: Fall foliage typically peaks in early to mid-October, although the exact timing varies each year. Use this peak fall foliage map to help choose your dates, and book accommodation as early as possible!
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Best Things to Do in Woodstock, Vermont
1. Explore Woodstock Central Street and The Green
The best place to begin your visit is in the center of Woodstock. Central Street is lined with independent shops, cafés, restaurants, and beautifully preserved historic buildings, while The Green sits just a few minutes away.
Take your time walking around the village and browsing the local stores. Some of the best stops include Yankee Bookshop, Vermont Flannel, and Clover Gift Shop. For coffee or breakfast, head to Mon Vert Cafe, one of my favorite places in Woodstock.
The Green is surrounded by some of the town’s most beautiful homes and buildings, including the Woodstock Inn & Resort. It’s particularly lovely in the fall when the trees surrounding the park turn red, orange, and gold.
Woodstock Town Hall Theatre is also nearby and hosts movies, concerts, and live performances throughout the year. Check the schedule before your visit if you’re looking for something to do in the evening.
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2. Walk through Middle Covered Bridge
You don’t need to leave the village to see one of Vermont’s famous covered bridges! Middle Covered Bridge crosses the Ottauquechee River just behind The Green, making it an easy stop while exploring downtown.
Although it looks historic, the current bridge was built in 1969 to replace an earlier structure. It was constructed using traditional methods and features a separate pedestrian walkway, so you can safely cross while taking in the views over the river.
Walk down to the riverbank for a different perspective of the bridge. The surrounding trees make it especially photogenic during fall, but it’s a lovely spot at any time of year.
3. Browse F.H. Gillingham & Sons
Browsing F.H. Gillingham & Sons is one of the best things to do in Woodstock, VT, especially if you want to pick up a few local products. This family-run general store has stood in the same building on Elm Street since 1886.
Inside, you’ll find Vermont maple syrup, local cheese, freshly baked goods, wine, clothing, books, toys, housewares, and plenty of souvenirs. The store still has many of its original details, including wooden shelves and old nail bins.
Even if you aren’t planning to buy anything, it’s worth stopping by while exploring the village. However, it’s a particularly good place to stock up on Vermont treats to take home.
4. Explore Marsh-Billings-Rockefeller National Historical Park
Marsh-Billings-Rockefeller National Historical Park tells the story of conservation and sustainable forestry in Vermont. The park covers 550 acres on the slopes of Mount Tom, with more than 20 miles of carriage roads and hiking trails winding through the forest.
At the center of the estate is the Marsh-Billings-Rockefeller Mansion, which was home to three generations of conservationists. You can explore the mansion on a guided or self-guided tour and walk through the surrounding gardens.
The park’s trails and grounds are free to visit and open throughout the year from dawn to dusk. The mansion, visitor center, and ranger-led programs operate seasonally, generally from Memorial Day weekend through the end of October.
Parking is available across the road at Billings Farm & Museum, making it easy to visit both attractions on the same day.
5. Visit Billings Farm & Museum
Directly across the road from Marsh-Billings-Rockefeller National Historical Park, Billings Farm & Museum combines a working dairy farm with exhibits about rural life in Vermont.
Your admission includes access to the animal barns, pastures, farm life exhibits, tractor collection, and the historic 1890 Farm Manager’s House. You can meet the farm’s Jersey cows, sheep, goats, chickens, and horses while learning more about traditional farming practices.
Daily programs vary throughout the year and may include butter-making demonstrations, wagon rides, historic cooking, and animal activities. The farm also hosts seasonal events, including harvest weekends and Christmas celebrations, so check the calendar before visiting.
Allow at least a couple of hours to explore the farm and museum, especially if you’re visiting with children.
6. Hike to South Peak on Mount Tom
For one of the best views over Woodstock, follow the trail to South Peak on Mount Tom. The overlook sits above the village and offers a beautiful view of the rooftops, church steeples, and surrounding hills.
The hike is approximately 4 miles round trip and is considered moderate, with a steady climb through the forest. You can begin at Faulkner Park, Prosper Road, or near Billings Farm & Museum, although the exact distance varies depending on your starting point.
If you have more time, extend your walk to The Pogue, a peaceful 14-acre pond surrounded by forest. The trails are especially beautiful in fall, but remember that South Peak can only be reached on foot.
7. Take in the views from Mount Peg
If you want a shorter alternative to Mount Tom, hike to the grassy overlook on Mount Peg. From the top, you can see across the Ottauquechee River Valley toward Billings Farm and Mount Tom.
The Summit Trail is around 2.5 miles round trip and is considered moderate. It begins with a short but fairly steep climb before becoming gentler as it continues through the forest.
The main trailhead is located on Golf Avenue, within walking distance of downtown Woodstock. Benches and picnic tables at the overlook make it a lovely place to stop for a snack while enjoying the view.
8. Visit Sugarbush Farm
Come hungry to Sugarbush Farm because the cheese and maple syrup tastings are easily the best part of the visit. The family-run farm sits around 15 minutes outside Woodstock and is free to explore.
Follow the short nature trail through the woods to learn how maple trees are tapped and the sap is collected. You can also visit the sugarhouse, look inside the cheese workroom, and stop by the small farm chapel hidden among the trees.
The farm shop offers several varieties of cheese and maple syrup to sample, along with jams, preserves, smoked meats, and other locally made products. This alone makes it one of the best things to do near Woodstock, Vermont!
There is no admission fee, but purchasing something from the shop is a great way to support the farm. The final stretch of the drive follows a narrow dirt road, so take it slowly.
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9. Shop at Woodstock Farmers’ Market
Despite the name, Woodstock Farmers’ Market is not a weekly outdoor market. It’s a year-round specialty grocery store located around one mile west of the village.
The shelves are filled with fresh produce, Vermont cheeses, maple products, craft beer, cider, wine, and other locally made goods. There is also a bakery, coffee counter, meat and seafood section, and a large selection of prepared food.
It’s a great place to pick up sandwiches, salads, and snacks before heading out for a hike or day trip. The market is open Tuesday through Sunday and closed on Mondays.
10. Drive through Taftsville Covered Bridge
Unlike Middle Covered Bridge, Taftsville Covered Bridge is genuinely historic. Built in 1836, it is one of the oldest surviving covered bridges in both Vermont and the United States.
The red timber bridge stretches 189 feet across the Ottauquechee River and remains open to vehicles. You can drive through it before stopping to see the structure from the riverbank, where you’ll also have a view of the nearby dam.
Taftsville is around five minutes east of downtown Woodstock. Parking near the bridge is limited, so make sure you pull completely off the road and avoid blocking local traffic.
11. Walk across Quechee Covered Bridge
Quechee Covered Bridge may not be as old as many of Vermont’s historic bridges, but its setting makes it well worth a stop. It crosses the Ottauquechee River beside the old mill that now houses Simon Pearce, with a waterfall and dam directly below.
A separate pedestrian walkway allows you to cross safely and look down over the river. You can also follow the path beside the mill for a better view of the bridge and waterfall together.
The bridge was originally built in 1970 and reconstructed after suffering extensive damage during Hurricane Irene in 2011. It’s located around 15 minutes from Woodstock and is easy to combine with Simon Pearce and Quechee Gorge.
12. Watch the glassblowers at Simon Pearce
Head downstairs at the Simon Pearce Mill to watch skilled artisans transform molten glass into vases, bowls, and other pieces. The glassblowing demonstrations are free to watch, and you can stay for as long as you like.
The workshop and flagship store occupy a former woolen mill beside the Ottauquechee River. After watching the glassblowers, browse the showroom upstairs or walk outside to see the waterfall, dam, and Quechee Covered Bridge.
The mill also has a popular restaurant overlooking the river if you want to stay for lunch or dinner. Glassblowing hours vary throughout the week, so check the schedule before visiting.
13. Visit Quechee Gorge
Quechee Gorge drops 165 feet down to the Ottauquechee River, making it the deepest gorge in Vermont. The easiest view is from the Route 4 bridge, where you can look directly into the gorge and across the surrounding forest.
For a closer look, follow the Quechee Gorge Trail from the visitor center toward the bottom of the gorge. The route is around 1.5 miles round trip and takes approximately 1.5 hours to complete.
You can also explore the woodland trails in Quechee State Park or stop at the visitor center to learn more about the gorge and how it was formed. The park and visitor facilities operate seasonally, so check the opening dates if you’re visiting outside summer or fall.
Quechee Gorge is around 15 minutes from Woodstock and only a short drive from Simon Pearce and Quechee Covered Bridge, so you can easily visit all three together.
Useful Info for Visiting Woodstock VT
Where to stay in Woodstock, Vermont
Staying in or close to the village center puts Woodstock’s shops, cafés, restaurants, and several of its main attractions within walking distance. It’s the most convenient option if you want to explore without getting in the car every time.
Properties outside the center tend to offer a quieter setting and more space, but you’ll need to drive into town. Accommodation in Woodstock fills up quickly during fall foliage season and holiday weekends, so book as early as possible if you’re visiting at a popular time.
Here are some of my top picks:
- Luxury: 506 On the River Inn Woodstock
- Mid-range: The Shire Woodstock
- Budget: The Vesper Woodstock
How to get to Woodstock, Vermont
The easiest way to get to Woodstock is by car. If you’re flying in, Burlington Airport is around 1.5 hours away, while Boston Logan Airport is approximately a 2.5-hour drive.
Woodstock is also easy to include in a longer New England road trip. It’s just over an hour from Stowe, around 1.5 hours from Burlington, and approximately 30 minutes from Killington, so it works well alongside other stops in Vermont.
Best time to visit Woodstock, Vermont
There really isn’t a bad time to visit Woodstock, but fall is easily the most popular season. The foliage usually peaks in early to mid-October, although the exact timing changes each year. This is also the busiest and most expensive period, so book your accommodation well in advance!
Late spring and summer are quieter, with warm weather and plenty of opportunities for hiking, cycling, and exploring the surrounding farms. Most seasonal attractions are also fully open during these months.
Winter brings snow, skiing, and Woodstock’s annual Wassail Weekend in December. The village looks beautiful decorated for Christmas, although you’ll need to be prepared for cold weather and potentially icy roads.
How to get around Woodstock VT
Downtown Woodstock is compact and easy to explore on foot. Central Street, The Green, Middle Covered Bridge, F.H. Gillingham & Sons, and several restaurants and cafés are all within a short walk of one another.
However, you’ll still want a car for most of the places outside the village, including Sugarbush Farm, Taftsville Covered Bridge, and the Quechee attractions. Parking is available throughout the area, but spaces in the center can fill up quickly during fall weekends.
