8 days in Vermont Itinerary

8 days in Vermont Itinerary

Created using Inspirock Vermont trip planner

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Route & dates

8 days in Vermont Itinerary

Start: New York City
Drive:  3 h 30 min
1
Bennington
— 1 night
Drive:  1 h 45 min
2
Woodstock
— 3 nights
Drive:  1 h 45 min
3
Burlington
— 3 nights
Fly:  4 h
End: New York City

1
night
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Start off your visit on the 27th (Fri): take in the views from Bridge at the Green, then experience rural life at Adams Farm, and then don't miss a visit to Jim McGrath Gallery and Studio. Get ready for a full day of sightseeing on the next day: get great views at Bennington Battle Monument, then take in nature's colorful creations at Hildene, The Lincoln Family Home, and then look for gifts at Vermont Country Store.

To see maps, photos, and more tourist information, read our Bennington day trip planning tool .

New York City to Bennington is an approximately 3.5-hour car ride. In December, Bennington is little chillier than New York City - with highs of 39°F and lows of 23°F. Cap off your sightseeing on the 28th (Sat) early enough to go by car to Woodstock.

Things to do in Bennington

Historic Sites Parks Museums

Side Trips

Wilmington, Bridge at the Green, Hildene, The Lincoln Family Home, Vermont Country Store
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Bennington Battle Monument ©
Bennington Battle Monument
Vermont Country Store ©
Vermont Country Store

3
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. You'll find plenty of places to visit near Woodstock: Dog Mountain Home of Stephen Huneck Gallery (in Saint Johnsbury), Killington Resort (in Killington) and Okemo Mountain Resort (in Ludlow). There's lots more to do: relax in the rural setting at Sugarbush Farm, steep yourself in history at Billings Farm & Museum, sample the tasty concoctions at Harpoon Brewery, and take in breathtaking views at Quechee Gorge.

For where to stay, more things to do, reviews, and more tourist information, read Woodstock trip planner .

Getting from Bennington to Woodstock by car takes about 2 hours. December in Woodstock sees daily highs of 35°F and lows of 20°F at night. Finish your sightseeing early on the 31st (Tue) so you can drive to Burlington.

Things to do in Woodstock

Parks Outdoors Winter Sports

Side Trips

Windsor, Killington Resort, Okemo Mountain Resort, Quechee Gorge, Dog Mountain Home of Stephen Huneck Gallery
Highlights from your plan
Sugarbush Farm ©
Sugarbush Farm
Killington Resort ©
Killington Resort

3
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. You'll find plenty of places to visit near Burlington: Stowe (Stowe Mountain Resort, Stowe Recreation Path, & more). And it doesn't end there: browse the eclectic array of goods at Church Street Marketplace, look for gifts at Lake Champlain Chocolates, brush up on your military savvy at Vermont National Guard Library & Museum, Inc., and walk around Waterfront Park.

To see maps, more things to do, photos, and more tourist information, you can read our Burlington trip itinerary builder .

Traveling by car from Woodstock to Burlington takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around 36°F in December, and nighttime lows around 23°F. Wrap up your sightseeing on the 3rd (Fri) to allow time to travel back home.

Things to do in Burlington

Parks Outdoors Trails

Side Trips

Stowe, Vermont National Guard Library & Museum, Inc., Shelburne Museum, 1st Republic Brewing Company
Highlights from your plan
Church Street Marketplace ©
Church Street Marketplace
Stowe Recreation Path ©
Stowe Recreation Path
Burlington Bike Path ©
Burlington Bike Path

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