Woodstock Vermont Things To Do
- Jun 9
- 6 min read
Updated: Jul 24
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Travel to Woodstock, Vermont to visit one of America’s most charming towns. Set at the foot of the majestic Green Mountains, Woodstock is the perfect jumping off point for long scenic drives, hikes through the forest, and antiquing expeditions into the Vermont countryside. Read on for ideas about the best things to do in Woodstock, Vermont.
VERMONT TOURS
WHY VISIT WOODSTOCK VERMONT
Woodstock is full of one-of-a-kind businesses that reflect Vermont’s rural culture and affinity for locally sourced ingredients and materials. Visitors flock to the area to enjoy the New England-styled architecture, covered bridges, farm-to-table eateries, and markets. Outside of town, there are miles of green pastures, mountains, and rambling rivers to explore.
WHERE IS WOODSTOCK VT
Nestled in the east-central part of the state, Woodstock VT is located in Windsor County at the foothills of the Green Mountain National Forest.
Just 2.5-hours north of Boston, Massachusetts, visitors will find great shopping, restaurants and outdoor activities to enjoy in the Woodstock region. Our post will highlight Woodstock Vermont things to do, and hit on attractions in the surrounding area.
The areas is best seen using a personal vehicle. Click here for information on Car Rentals in Vermont.
THINGS TO DO IN WOODSTOCK VERMONT
Joe and I’s favorite time of year to visit Woodstock, Vermont is in the autumn when the maple trees are a-blaze, and the weather is perfect for hiking and touring. We also love the holiday season when Woodstock’s downtown twinkles with lights and decorations.
Here is a list of some of our favorite things to do in Woodstock, Vermont, and the surrounding area:
Stroll the Shops of Downtown Woodstock
Woodstock is often touted as one of the prettiest towns in America. Approaching the village, New England-style colonials with white picket fences line the streets. The downtown area is made up largely of one-of-a-kind businesses.
Spend the day shopping the artsy boutiques, eateries, and galleries. Some customers return year after year to shop and eat at F. H. Gillingham & Sons General Store, Unicorn’s, and the Prince and the Pauper Restaurant.
At the edge of town there is a covered bridge and much-loved green to stroll. Along one side of the green, the luxurious Woodstock Inn and Resort is located. Enjoying lunch in the resort’s dining room is a popular thing to do in Woodstock.
TRIP ESSENTIALS
In Vermont, and almost every travel destination, I find myself reaching for my Eddie Bauer Rainfoil Jacket, Frogg Toggs Hat, and Merrell Hiking Boots.
Other items I rely on include my Huk Sunglasses and Contigo Autoseal Water Bottle (no spills in the backpack).
But by far, my number one can’t-do-without essential is my Sony RX100 Compact Camera. It fits perfectly into a pocket. Or, mounted on a Mini-Tripod it slips into my Travelon Sling Bag.
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Take a Scenic Drive
Woodstock is located in Windsor County, Vermont. The geography of the county includes the rugged mountains and rolling pastures for which Vermont is famous. The county is dotted with dairy farms, dirt roads, and white steepled churches.
One of the best things to do in Woodstock, Vermont is to get in the car and drive. The Crossroad of Vermont Byway (Route 4) runs through the area, and is a good place to begin your Vermont road trip. Then, throw away the map and see where the tar (or gravel) takes you.
Learn about Farming at the Billings Farm Museum
The Billings Farm Museum in Woodstock, Vermont is a great day trip for couples and families. Billings teaches about past- and present-day New England farm life. Inside of a large barn there are museum exhibits re-creating 19th century farm life. Onsite there is a functioning dairy operation, and an excellent gift shop. Spread across the grounds there are gardens and barns full of animals to wander.
Explore the Area’s Four Covered Bridges
A 37-mile route takes in four historic covered bridges (Middle, Taftsville, Quechee, and Cornish-Windsor). Designed as a loop, the trip can be started at any bridge. If you are staying in Woodstock, begin at the Middle Covered Bridge. Next, move on to the red Taftsville Bridge.
Plan to stop for a while at the Quechee Covered Bridge. View the bridge and Mill Pond Falls from Quechee Park. Then, trek to the nearby Simon Peace factory store. Tour the company store before enjoying a meal at its restaurant overlooking the bridge.
Make your last stop of the day the Cornish-Windsor Covered Bridge on the Vermont-New Hampshire Border.
WOODSTOCK AREA HOTELS
Visit Quechee Gorge
Quechee Gorge is a 165’-deep ravine towering above the Ottauquechee River. The area is part of the Quechee Gorge State Park, and is a popular Vermont attraction. A bridge with wide sidewalks runs over the Gorge. Most visitors park in the lots on either edge of the bridge, and take snapshots from the walkway.
Additional ways to experience Quechee Gorge include hiking State Park trails that run along the gorge; or taking a Quechee Segway Tour of the park.
Hike to the Summit of Mount Ascutney
In Windsor County, Mt. Ascutney soars into the sky. The mountain is laced with a network of trails. Ascutney’s rocky summit is a favorite with area hikers, bikers, and hang gliders.
For day-trippers who do not want to scale the mountain’s entire 3,144-feet, the 3.7-mile Mount Ascutney Parkway takes visitors up most of the mountain via a windy tar road. From there, it is about a 1-mile hike to the summit. At Ascutney’s peak, visitors can climb a fire tower and admire the views from a nearby hang glider platform.
Go Antiquing at Quechee Gorge Village
Along scenic Route 4 in Quechee, visitors will find two wonderful shopping and antique malls.
The Quechee Antiques Collaborative has over 165 dealers displaying antiques and fine arts on three floors of a converted farm house gallery. The collaborative specializes in New England country furniture, and sterling and coin silver.
Quechee Gorge Village offers Vermont-themed eateries, shopping, and attractions for the entire family. The village houses a General Store, Cabot Cheese store, farm stand, toy shop, antique shop, winery, restaurants, and more. It’s great fun, don’t miss it!
Tour the Marsh-Billings-Rockefeller National Historic Park
A visit to Woodstock’s Marsh-Billings-Rockefeller National Historic Park is a wonderful way to spend an afternoon. The park is home to an 1800s Queen Anne – style mansion which is open for guided tours. Attached to the mansion, there are gardens and a greenhouse to view.
The expansive grounds behind the mansion are crisscrossed with 20-miles of gravel roads and hiking trails which can be explored on your own. The park service also keeps a calendar of guided hikes, wagon rides, and other outdoor activities that are offered throughout the year.
Ride a Gondola at Killington Ski Resort
The Killington Ski Resort is located about 30-minutes west of Woodstock, Vermont. To get there, drive along Route 4 to Killington’s K-1 base lodge. In the summer and fall, the Killington gondola takes visitors up the mountain some 4,140 feet. After disembarking the lift, follow signs to the peak (about a 10-minute hike). The short rocky path brings visitors to the 4,241’ top of the Killington Ski Resort.
PACKING ESSENTIALS
We rely on a combination of bags: Our Level-8 28” and Level-8 20” spinners are fun and stylish. Our Delsey Helium 28” hardshell is a workhorse. Our Tomtoc Backpack is great for short trips.
Randy doesn’t use them, but I swear by segregating items into Compression Packing Cubes and Wet Bags.
For security, we place an Apple Air Tag in each bag, and keep a supply of RFID Blocking Sleeves on hand.
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Shop Windsor Artisans Park
The Windsor Vt. Artisans Park is an assembly of Vermont-based companies housed in a business park. The park is located about 11-miles east of Woodstock.
Onsite there is the Harpoon Brewery, Simon Pearce Glassworks and Pottery, SILO Distillery, Path of Life Sculpture Garden, Great River Outfitters, Blake Hill Preserves, and Artisan Eats.
At Harpoon Brewery and Simon Pearce, you can view the brewing and glass blowing processes. The park is spacious, well-landscaped, and there is plenty of free parking.
Goodbye for now from the Green Mountain State, Laura and Randy
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