8 days in Vermont Itinerary

8 days in Vermont Itinerary

Created using Inspirock Vermont travel route builder

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Route & dates

8 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:  45​min
4
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. On the 17th (Thu), admire the masterpieces at Bennington Museum, then appreciate the history behind Bennington Battle Monument, and then stroll the grounds of The Old First Church. Get ready for a full day of sightseeing on the next day: look for gifts at Bennington Potters, stroll the grounds of New Catholic Cemetery, then take in the views from Silk Road Covered Bridge, and finally cruise along Molly Stark Trail.

To find photos, where to stay, traveler tips, and more tourist information, you can read our Bennington trip planner .

New York City to Bennington is an approximately 3.5-hour car ride. In October, Bennington is a bit cooler than New York City - with highs of 62°F and lows of 41°F. Cap off your sightseeing on the 18th (Fri) early enough to go by car to Woodstock.

Things to do in Bennington

Historic Sites Outdoors Scenic Drive
Highlights from your plan
The Old First Church ©
The Old First Church
Bennington Battle Monument ©
Bennington Battle Monument
Bennington Museum ©
Bennington Museum

1
night
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Start off your visit on the 19th (Sat): relax in the rural setting at Billings Farm & Museum, then relax in the rural setting at Sugarbush Farm, and then explore the stunning scenery at Quechee Gorge.

To see other places to visit, traveler tips, where to stay, and more tourist information, use the Woodstock road trip planning site .

Traveling by car from Bennington to Woodstock takes 2 hours. In October, plan for daily highs up to 62°F, and evening lows to 40°F. Wrap up your sightseeing on the 19th (Sat) to allow time to drive to Stowe.

Things to do in Woodstock

Historic Sites Nature Museums

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 20th (Sun): stop by Cabot Farmers' Store, then take in the awesome beauty at Mount Mansfield State Forest, and then trek along Stowe Recreation Path. Get ready for a full day of sightseeing on the 21st (Mon): discover the riches below the earth's surface at Rock of Ages, admire the landmark architecture of Vermont State House, and then experience rural life at Morse Farm Maple Sugarworks.

To find traveler tips, ratings, maps, and tourist information, read Stowe trip website .

You can drive from Woodstock to Stowe in 1.5 hours. Alternatively, you can do a combination of bus and train; or take a train. October in Stowe sees daily highs of 60°F and lows of 39°F at night. Wrap up your sightseeing on the 21st (Mon) early enough to drive to Burlington.

Things to do in Stowe

Parks Nature Outdoors

Side Trips

Montpelier, Cabot Farmers' Store, Rock of Ages Granite Quarry
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Mount Mansfield State Forest ©
Mount Mansfield State Forest
Morse Farm Maple Sugarworks ©
Morse Farm Maple Sugarworks

3
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Take a break from Burlington with a short trip to Fort Ticonderoga in Ticonderoga, about 1h 15 min away. And it doesn't end there: browse the eclectic array of goods at Church Street Marketplace, stroll through Burlington Bike Path, examine the collection at Shelburne Museum, and relax in the rural setting at Shelburne Farms.

To see more things to do, photos, maps, and tourist information, go to the Burlington day trip app .

Traveling by car from Stowe to Burlington takes an hour. Alternatively, you can take a bus. In October, daytime highs in Burlington are 62°F, while nighttime lows are 44°F. Wrap up your sightseeing by early afternoon on the 24th (Thu) to allow enough time to travel back home.

Things to do in Burlington

Historic Sites Museums Parks

Side Trips

Shelburne, Fort Ticonderoga
Highlights from your plan
Fort Ticonderoga ©
Fort Ticonderoga
Shelburne Museum ©
Shelburne Museum
Church Street Marketplace ©
Church Street Marketplace

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