Woodstock

Travel Guide

A red convertible car parked in front of a brick house with black shutters and a white picket fence.
A street with various shops, including 'The Prince & The Pauper' and 'Philox'.
A river with rocks, surrounded by trees with orange leaves, a grassy area, and a building in the background.
A wooden covered bridge with signs reading "Woodstock Middle Bridge 1969" and "Slippery When Wet."
A historic brick building with a sign reading "Woodstock Pharmacy" and various storefronts below.

In the seat of Windsor County, discover Vermont’s only national park, three covered bridges and dozens of shops and restaurants.

Travel back to a bygone time in Woodstock, Vermont. The picturesque town, located in the midst of the Green Mountains, remains remarkably similar in appearance to how it looked a century ago. Vermont is known for its stunning nature and charming villages in Woodstock, experience both in one place.

Discover the shopping, dining and lodging attractions of downtown Woodstock. From antiques to artwork, find something to please any shopper. Explore the beautifully preserved 19th-century brick buildings that line the streets.

Covered bridges were once common throughout New England, but now few survive. Woodstock is home to not one, but three spanning the Ottauquechee River. Try to find them all. Lincoln Bridge, a plain wooden structure, is the simplest of the three. Recognise Taftsville Bridge by its distinctive red paint. Get your camera ready at Middle Bridge, known for its intricate diamond windows.

Explore the Marsh-Billings-Rockefeller National Historical Park, dedicated to three individuals who had tremendous influence in fostering conservation and stewardship of America’s landscapes. Trek to the Pogue, a beautiful mountain pond, and learn about the area’s history and future on a guided ranger tour. Visit the stately brick George Perkins Marsh Boyhood Home. Check out the paintings and photographs inside and relax in its manicured gardens.

Discover Vermont’s rural heritage at Billings Farm and Museum. Explore the 1,000-acre (400-hectare) working dairy farm. Watch the afternoon milking and meet cows, sheep, horses, oxen and more through interactive programmes. Check out historic exhibits in the 1890 Farm House and learn about life on a 19th-century farm.

Drive 10 minutes north from the town centre to Suicide Six. Go skiing or snowboarding down its snowy slopes in winter months. Have fun at your own pace on trails ranging from beginner to black diamond.

To experience Vermont’s scenery and small-town charm in one place, visit Woodstock. With the Green Mountains at its doorstep, go from browsing galleries in town to traversing wilderness trails in the forest in just a few minutes.

Where to stay in Woodstock

Find the best Woodstock areas for the activities you enjoy most.

West Woodstock

Visitors highly recommend West Woodstock for its abundant dining options, and you can make a stop by Union Arena Community Center while you're in town.

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is S$646 per night from 10 Nov to 11 Nov
S$646
10 Nov - 11 Nov
includes taxes & fees
Stay at this luxury resort in Woodstock. Enjoy free Wi-Fi, free valet parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (617 reviews)
"Room was spacious and very clean upon arrival. Staff was also very attentive and took care all our needs."

Reviewed on 11 Oct, 2026

Woodstock Inn & Resort
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
The price is S$173 per night from 3 Nov to 4 Nov
S$173
3 Nov - 4 Nov
includes taxes & fees
Stay at this B&B in Woodstock. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast in their reviews. Popular attractions ...
The Jackson
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is S$255 per night from 4 Nov to 5 Nov
S$255
4 Nov - 5 Nov
includes taxes & fees
Stay at this family-friendly hotel in Woodstock. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff ...
On The River Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
3387 East Mountain Road Killington VT
Stay at this ski cabin in Killington. Enjoy free Wi-Fi, free parking and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage I ...
9/10 Wonderful! (69 reviews)
"Property was good. We founded a lot of cobble webs around the house. The stove was dirty when we used and made a horrible smell of burned. The guys next door were very loud at 3am and we couldn't sleep till they left around 5-6am. Will for sure be back if we have a chance. The place is well located ..."

Reviewed on 5 Oct, 2026

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Mountain Green

Mountain Green

2 out of 5
133 E Mountain Rd Killington Killington VT
Stay at this condo in Killington. Enjoy free parking, a picnic area and an indoor pool. Popular attractions Killington Resort and Black Dog Sports are located ...
Mountain Green
Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

3 out of 5
122 Best Rd Windsor VT
Stay at this cabin in Windsor. Enjoy free Wi-Fi, free parking and a garden. Popular attractions Hartland Public Library and Path of Life Garden are located ...
9.8/10 Exceptional! (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views!"

Reviewed on 5 Jan, 2026

Fat Sheep Farm & Cabins
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Woodstock attractions