5 days in Vermont Itinerary

5 days in Vermont Itinerary

Created using Inspirock Vermont route planner

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Route & dates

5 days in Vermont Itinerary

Start: Newark
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:  5​h 45​min
End: Newark

1
night
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. On the 14th (Sat), take in nature's colorful creations 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: admire the masterpieces at Bennington Museum, stroll the grounds of The Old First Church, pause for some photo ops at Bennington Battle Monument, then explore the different monuments and memorials at New Catholic Cemetery, and finally make a trip to Silk Road Covered Bridge.

Start your trip to Bennington by creating a personalized itinerary on Inspirock.

Newark to Bennington is an approximately 3.5-hour car ride. Traveling from Newark in September, expect Bennington to be little chillier, temps between 74°F and 48°F. Wrap up your sightseeing on the 15th (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 16th (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.

For ratings, maps, photos, and other tourist information, you can read our Woodstock trip planner .

Drive from Bennington to Woodstock in 2 hours. In September in Woodstock, expect temperatures between 75°F during the day and 50°F at night. Finish your sightseeing early on the 16th (Mon) so you can drive to Stowe.

Things to do in Woodstock

Museums Nature Parks

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.
Start off your visit on the 17th (Tue): trek along Burlington Bike Path, stop by Cabot Farmers' Store, and then hike along Stowe Recreation Path. On your second day here, hunt for treasures at Church Street Marketplace, examine the collection at Shelburne Museum, and then walk around Waterfront Park.

To find traveler tips, where to stay, photos, and tourist information, you can read our 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 September, daily temperatures in Stowe can reach 73°F, while at night they dip to 48°F. Finish your sightseeing early on the 18th (Wed) to allow enough time to travel back home.

Things to do in Stowe

Parks Outdoors Trails

Side Trips

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

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