5 days in Vermont Itinerary

5 days in Vermont Itinerary

Created using Inspirock Vermont vacation planner

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Route & dates

5 days in Vermont Itinerary

Start: New York City
Drive:  4​h
1
Bennington
— 1 night
Drive:  1​h 45​min
2
Woodstock
— 1 night
Drive:  1​h 30​min
3
Stowe
— 2 nights
Drive:  6​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 10th (Sat): admire the natural beauty at Hildene, The Lincoln Family Home and then look for gifts at Northshire Bookstore. Get ready for a full day of sightseeing on the next day: stroll the grounds of New Catholic Cemetery, get engrossed in the history at Bennington Museum, then take some stellar pictures from Bennington Battle Monument, then explore the different monuments and memorials at The Old First Church, and finally snap pictures at Silk Road Covered Bridge.

For more things to do, reviews, maps, and other tourist information, use the Bennington vacation planner .

New York City to Bennington is an approximately 3.5-hour car ride. In August, Bennington is slightly colder than New York City - with highs of 79°F and lows of 55°F. Wrap up your sightseeing on the 11th (Sun) to allow time to drive to Woodstock.

Things to do in Bennington

Historic Sites Museums Parks

Side Trip

Manchester
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Bennington Battle Monument ©
Bennington Battle Monument
New Catholic Cemetery ©
New Catholic Cemetery

1
night
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Start off your visit on the 12th (Mon): contemplate the long history of Billings Farm & Museum, relax in the rural setting at Sugarbush Farm, and then take in breathtaking views at Quechee Gorge.

To find reviews, other places to visit, and more tourist information, use the Woodstock online trip builder .

You can drive from Bennington to Woodstock in 2 hours. In August in Woodstock, expect temperatures between 81°F during the day and 56°F at night. Wrap up your sightseeing on the 12th (Mon) to allow time to drive to Stowe.

Things to do in Woodstock

Museums Historic Sites Nature

Side Trip

Quechee Gorge
Highlights from your plan
Billings Farm & Museum ©
Billings Farm & Museum
Sugarbush Farm ©
Sugarbush Farm
Quechee Gorge ©
Quechee Gorge

2
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.
Kick off your visit on the 13th (Tue): hike along Burlington Bike Path, look for gifts at Cabot Farmers' Store, and then trek along Stowe Recreation Path. Get ready for a full day of sightseeing on the 14th (Wed): stroll around Waterfront Park, hunt for treasures at Church Street Marketplace, and then see the interesting displays at Shelburne Museum.

To find traveler tips, where to stay, other places to visit, and other tourist information, refer to the Stowe trip planner .

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, daily temperatures in Stowe can reach 78°F, while at night they dip to 55°F. Wrap up your sightseeing on the 14th (Wed) early enough to drive back home.

Things to do in Stowe

Parks Trails Outdoors

Side Trips

Burlington, Cabot Farmers' Store, Shelburne Museum
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Shelburne Museum ©
Shelburne Museum
Church Street Marketplace ©
Church Street Marketplace

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