14 days in Vermont Itinerary

14 days in Vermont Itinerary

Created using Inspirock Vermont trip itinerary planner

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Route & dates

14 days in Vermont Itinerary

Start: Charlotte
Fly + Drive:  7​h 15​min
1
Bennington
— 6 nights
Drive:  1​h 45​min
2
Woodstock
— 3 nights
Drive:  1​h 45​min
3
Burlington
— 3 nights
Fly:  4​h 15​min
End: Charlotte

6
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Venture out of the city with trips to Dr. Seuss National Memorial Sculpture Garden (in Springfield), Lake George (Lake George, The Fort William Henry Museum & Restoration, & more) and Saratoga Race Course (in Saratoga Springs). There's much more to do: explore the world behind art at Norman Rockwell Museum, take an in-depth tour of Bennington Museum, stroll the grounds of New Catholic Cemetery, and get outside with Square Eddy Expeditions.

For more things to do, photos, reviews, and other tourist information, use the Bennington online holiday planner .

Charlotte to Bennington is an approximately 7.5-hour combination of flight and car. You can also drive. Expect a bit cooler temperatures when traveling from Charlotte in September; daily highs in Bennington reach 74°F and lows reach 48°F. Wrap up your sightseeing on the 1st (Tue) to allow time to drive to Woodstock.

Things to do in Bennington

Museums Parks Outdoors

Side Trips

Lake George, The Clark Art Institute, Saratoga Race Course, Six Flags New England, The Berkshire Carousel
Highlights from your plan
Bennington Battle Monument ©
Bennington Battle Monument
Norman Rockwell Museum ©
Norman Rockwell Museum
Lake George ©
Lake George

3
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Change things up with these side-trips from Woodstock: Flume Gorge (in Franconia) and Zipline (in Lincoln). Next up on the itinerary: experience rural life at Sugarbush Farm, explore the stunning scenery at Quechee Gorge, take your sightseeing to a higher altitude at Mount Tom, and explore the wealth of natural beauty at Marsh - Billings - Rockefeller National Historical Park.

For maps, photos, where to stay, and more tourist information, read our Woodstock itinerary planner .

Getting from Bennington to Woodstock by car takes about 2 hours. Expect a daytime high around 62°F in October, and nighttime lows around 40°F. Finish your sightseeing early on the 5th (Sat) to allow enough time to drive to Burlington.

Things to do in Woodstock

Parks Nature Historic Sites

Side Trips

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

3
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Get out of town with these interesting Burlington side-trips: Stowe (Mount Mansfield State Forest & Stowe Recreation Path). There's much more to do: browse the eclectic array of goods at Church Street Marketplace, examine the collection at Shelburne Museum, contemplate the long history of Shelburne Farms, and contemplate in the serene atmosphere at Round Church.

To find traveler tips, reviews, maps, and tourist information, you can read our Burlington online sightseeing planner .

Traveling by car from Woodstock to Burlington takes 2 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 62°F, and evening lows to 44°F. Wrap up your sightseeing by early afternoon on the 8th (Tue) to allow enough time to travel back home.

Things to do in Burlington

Parks Outdoors Trails

Side Trips

Stowe, Shelburne, Round Church
Highlights from your plan
Church Street Marketplace ©
Church Street Marketplace
Burlington Bike Path ©
Burlington Bike Path
Waterfront Park ©
Waterfront Park

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