5 days in Vermont Itinerary

5 days in Vermont Itinerary

Created using Inspirock Vermont travel planner

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Route & dates

5 days in Vermont Itinerary

Start: New York City
Drive:  4​h
1
Bennington
— 1 night
Drive:  1​h 45​min
2
Woodstock
— 2 nights
Drive:  1​h 45​min
3
Burlington
— 1 night
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 (Sat), take in nature's colorful creations at Hildene, The Lincoln Family Home, then take in the views from Papermill Village Bridge, and then explore the different monuments and memorials at The Old First Church. Here are some ideas for day two: look for gifts at Manchester Hot Glass, admire the sheer force of Lye Brook Falls, then identify plant and animal life at Equinox Preservation Trust, and finally take in the exciting artwork at Norman Rockwell Exhibition.

To see photos and more tourist information, read Bennington driving holiday planner.

New York City to Bennington is an approximately 3.5-hour car ride. Traveling from New York City in June, Bennington is little chillier at night with lows of 53°F. Wrap up your sightseeing on the 16th (Sun) early enough to drive to Woodstock.

Things to do in Bennington

Parks Wildlife Museums

Side Trips

Manchester, Norman Rockwell Exhibition
Highlights from your plan
The Old First Church ©
The Old First Church
Equinox Preservation Trust ©
Equinox Preservation Trust
Lye Brook Falls ©
Lye Brook Falls

2
nights
Woodstock

Woodstock
Woodstock is the shire town of Windsor County, Vermont, United States. Kick off your visit on the 17th (Mon): take in the dramatic scenery at Buttermilk Falls, contemplate the long history of President Calvin Coolidge State Historic Site, and then contemplate the long history of FH Gillingham & Sons General Store. On the next day, hike along Thundering Falls Trail, then contemplate the long history of Calvin Coolidge Homestead, and then take in the awesome beauty at Mount Tom.

To find photos, ratings, more things to do, and tourist information, read our Woodstock trip planner .

You can drive from Bennington to Woodstock in 2 hours. June in Woodstock sees daily highs of 77°F and lows of 53°F at night. Wrap up your sightseeing on the 18th (Tue) early enough to drive to Burlington.

Things to do in Woodstock

Parks Historic Sites Nature

Side Trips

Plymouth, Thundering Falls Trail, Buttermilk Falls
Highlights from your plan
Mount Tom ©
Mount Tom
FH Gillingham & Sons General Store ©

1
night
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Kick off your visit on the 19th (Wed): examine the collection at Shelburne Museum, then do a tasting at Shelburne Vineyard, then sample the tasty concoctions at Fiddlehead Brewing Company, and finally enjoy the sand and surf at North Beach Park.

To see maps, ratings, other places to visit, and more tourist information, use the Burlington trip itinerary maker tool .

Drive from Woodstock to Burlington in 2 hours. Alternatively, you can take a bus. In June, daytime highs in Burlington are 77°F, while nighttime lows are 57°F. Finish your sightseeing early on the 19th (Wed) to allow enough time to travel back home.

Things to do in Burlington

Outdoors Beaches Parks

Side Trip

Shelburne
Highlights from your plan
North Beach Park ©
North Beach Park
Shelburne Museum ©
Shelburne Museum
Shelburne Vineyard ©
Shelburne Vineyard

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