3 days in Vermont Itinerary

3 days in Vermont Itinerary

Created using Inspirock Vermont travel planner

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Route & dates

3 days in Vermont Itinerary

Start: New York City
Drive:  4​h 30​min
1
Bennington
— Few hours
Drive:  1​h 45​min
2
Woodstock
— 2 nights
Drive:  5​h
End: New York City

few
hours
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Start off your visit on the 14th (Mon): look for gifts at The Apple Barn and Country Bake Shop, take in the views from Silk Road Covered Bridge, and then stroll the grounds of The Old First Church.

To find where to stay and other tourist information, read Bennington travel route planner .

New York City to Bennington is an approximately 3.5-hour car ride. Traveling from New York City in October, things will get little chillier in Bennington: highs are around 62°F and lows about 41°F. Finish your sightseeing early on the 14th (Mon) to allow enough time to drive to Woodstock.

Things to do in Bennington

Shopping Historic Sites
Highlights from your plan
The Old First Church ©
The Old First Church
Silk Road Covered Bridge ©
Silk Road Covered Bridge

2
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Kick off your visit on the 15th (Tue): contemplate the long history of Calvin Coolidge Homestead, take in the dramatic scenery at Buttermilk Falls, then hike along Thundering Falls Trail, and finally steep yourself in history at FH Gillingham & Sons General Store. Get ready for a full day of sightseeing on the next day: take in the views from Cornish-Windsor Bridge, get curious at Montshire Museum of Science, then make a trip to Taftsville Covered Bridge, and finally take a peaceful walk through Mount Tom.

To find other places to visit, traveler tips, maps, and more tourist information, read Woodstock holiday planning site .

Traveling by car from Bennington to Woodstock takes 2 hours. In October, daily temperatures in Woodstock can reach 62°F, while at night they dip to 40°F. Finish your sightseeing early on the 16th (Wed) so you can drive back home.

Things to do in Woodstock

Parks Nature Trails

Side Trips

Thundering Falls Trail, Cornish-Windsor Bridge, Montshire Museum of Science, Calvin Coolidge Homestead, Buttermilk Falls
Highlights from your plan
Mount Tom ©
Mount Tom
Montshire Museum of Science ©
Montshire Museum of Science
FH Gillingham & Sons General Store ©

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