7 days in Vermont Itinerary

7 days in Vermont Itinerary

Created using Inspirock Vermont tour builder

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Route & dates

7 days in Vermont Itinerary

Start: Boston
Drive:  3​h
1
Bennington
— 1 night
Drive:  1​h 45​min
2
Woodstock
— 2 nights
Drive:  1​h 30​min
3
Stowe
— 3 nights
Drive:  3​h 30​min
End: Boston

1
night
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. On the 4th (Sun), take in the views from Bridge at the Green, then browse the exhibits of Hildene, The Lincoln Family Home, and then stroll the grounds of The Old First Church. On the next day, stop by Bringing You Vermont, then take some stellar pictures from Bennington Battle Monument, then explore the world behind art at Bennington Museum, and finally take your sightseeing to a higher altitude at Equinox Mountain.

Quickly create a custom-made itinerary for Bennington using our trip planner.

Boston to Bennington is an approximately 3.5-hour car ride. Traveling from Boston in August, plan for little chillier nights in Bennington, with lows around 55°F. Cap off your sightseeing on the 5th (Mon) early enough to go by car to Woodstock.

Things to do in Bennington

Parks Museums Nature

Side Trips

Arlington, Hildene, The Lincoln Family Home
Highlights from your plan
Hildene, The Lincoln Family Home ©
Bennington Battle Monument ©
Bennington Battle Monument
Bennington Museum ©
Bennington Museum

2
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. On the 6th (Tue), experience rural life at Sugarbush Farm, take in breathtaking views at Quechee Gorge, and then look for gifts at Vermont Country Store. Get ready for a full day of sightseeing on the 7th (Wed): explore the wealth of natural beauty at Marsh - Billings - Rockefeller National Historical Park, then take in the views from Taftsville Covered Bridge, and then steep yourself in history at Calvin Coolidge Homestead.

To see traveler tips, more things to do, reviews, and other tourist information, use the Woodstock trip itinerary planner.

You can drive from Bennington to Woodstock in 2 hours. In August, plan for daily highs up to 81°F, and evening lows to 56°F. Finish your sightseeing early on the 7th (Wed) so you can drive to Stowe.

Things to do in Woodstock

Nature Parks Historic Sites

Side Trips

Calvin Coolidge Homestead, Quechee Gorge, Vermont Country Store
Highlights from your plan
Quechee Gorge ©
Quechee Gorge
Sugarbush Farm ©
Sugarbush Farm

3
nights
Stowe

Stowe ©
Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
Explore Stowe's surroundings by going to Shelburne (Shelburne Museum & Shelburne Farms) and Burlington (Vintage Photography Emporium, Church Street Marketplace, & more). There's lots more to do: hike along Stowe Recreation Path, admire the sheer force of Moss Glen Falls, stop by Laughing Moon Chocolates, and take in the awesome beauty at Mount Mansfield State Forest.

To find where to stay, reviews, ratings, and more tourist information, read Stowe trip website .

Traveling by car from Woodstock to Stowe takes 1.5 hours. Alternatively, you can do a combination of bus and train; or take a train. In August, daytime highs in Stowe are 78°F, while nighttime lows are 55°F. Finish up your sightseeing early on the 10th (Sat) so you can go by car back home.

Things to do in Stowe

Parks Outdoors Nature

Side Trips

Burlington, Shelburne
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Shelburne Museum ©
Shelburne Museum
Burlington Bike Path ©
Burlington Bike Path

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