7 days in Vermont Itinerary

7 days in Vermont Itinerary

Created using Inspirock Vermont tour itinerary planner

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Route & dates

7 days in Vermont Itinerary

Start: New York City
Drive:  3​h 30​min
1
Bennington
— 1 night
Drive:  1​h 45​min
2
Woodstock
— 2 nights
Drive:  1​h 45​min
3
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 15th (Tue), take in the views from Burt Henry Covered Bridge, make a trip to Silk Road Covered Bridge, and then explore the different monuments and memorials at The Old First Church. Here are some ideas for day two: take in the dramatic scenery at Lye Brook Falls, then look for all kinds of wild species at Equinox Preservation Trust, then contemplate the long history of Robert Frost Stone House Museum, and finally look for gifts at Bennington Potters.

To see maps, ratings, and more tourist information, read Bennington journey maker site .

New York City to Bennington is an approximately 3.5-hour car ride. Plan for a bit cooler temperatures traveling from New York City in October, with highs in Bennington at 62°F and lows at 41°F. Finish up your sightseeing early on the 16th (Wed) so you can go by car to Woodstock.

Things to do in Bennington

Parks Wildlife Nature

Side Trips

Manchester, Robert Frost Stone House Museum
Highlights from your plan
Silk Road Covered Bridge ©
Silk Road Covered Bridge
Equinox Preservation Trust ©
Equinox Preservation Trust
The Old First Church ©
The Old First Church

2
nights
Woodstock

Woodstock
Woodstock is the shire town of Windsor County, Vermont, United States. Kick off your visit on the 17th (Thu): contemplate the long history of President Calvin Coolidge State Historic Site, then steep yourself in history at Calvin Coolidge Homestead, and then sample the tasty concoctions at Long Trail Brewing Company. Get ready for a full day of sightseeing on the next day: contemplate the waterfront views at Ottaquechee River, take in the awesome beauty at Mount Tom, then take in the views from Taftsville Covered Bridge, and finally snap pictures at Cornish-Windsor Bridge.

To find maps, more things to do, reviews, and other tourist information, you can read our Woodstock tour itinerary maker app .

You can drive from Bennington to Woodstock in 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 18th (Fri) to allow enough time to drive to Burlington.

Things to do in Woodstock

Historic Sites Nature Parks

Side Trips

Plymouth, Long Trail Brewing Company, Cornish-Windsor Bridge
Highlights from your plan
Mount Tom ©
Mount Tom
Long Trail Brewing Company ©
Long Trail Brewing Company

3
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Your day-by-day itinerary now includes Lake Champlain. Discover out-of-the-way places like Hope Cemetery and The Alchemist. Deepen your sense of the past at sights like Ethan Allen Homestead and Round Church. Venture out of the city with trips to Craft Beer Cellar (in Waterbury), Stowe (Toll Rd & Gold Brook Covered Bridge (Emily's Covered Bridge)) and Boyden Valley Winery & Spirits (in Cambridge). There's still lots to do: sample the tasty concoctions at Switchback Brewing and enjoy the sand and surf at North Beach Park.

To find ratings, photos, and other tourist information, go to the Burlington trip itinerary planner .

Getting from Woodstock to Burlington by car takes about 2 hours. Other options: take a bus. In October in Burlington, expect temperatures between 62°F during the day and 44°F at night. Wrap up your sightseeing on the 21st (Mon) to allow time to travel back home.

Things to do in Burlington

Outdoors Parks Breweries & Distilleries

Side Trips

Stowe, Round Church, Craft Beer Cellar, Lake Champlain, Hope Cemetery
Highlights from your plan
Lake Champlain ©
Lake Champlain
Boyden Valley Winery & Spirits ©
Boyden Valley Winery & Spirits
Hope Cemetery ©
Hope Cemetery

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