5 days in Boston & Vermont Itinerary

5 days in Boston & Vermont Itinerary

Created using Inspirock United States trip maker

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Route & dates

5 days in Boston & Vermont Itinerary

Start: New York City
bus + Fly:  3​h
1
Boston
— 2 nights
Fly:  2​h 30​min
2
Woodstock
— 1 night
Drive:  1​h 45​min
3
Burlington
— 1 night
Fly:  4​h
End: New York City

2
nights
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Visiting Nantasket Beach and National Monument to the Forefathers will get you outdoors. Discover out-of-the-way places like Back Bay and Jenney Museum. Explore the numerous day-trip ideas around Boston: Cape Cod Canal (in Buzzards Bay) and Pilgrim Hall Museum (in Plymouth). The adventure continues: contemplate the long history of Hancock-Clarke House, explore the galleries of Buckman Tavern, and admire the masterpieces at Museum of Fine Arts.

To find photos, maps, ratings, and tourist information, read Boston trip planner.

New York City to Boston is an approximately 3-hour combination of bus and flight. You can also fly; or drive. Traveling from New York City in August, Boston is little chillier at night with lows of 65°F. Finish up your sightseeing early on the 31st (Sat) so you can travel to Woodstock.

Things to do in Boston

Museums Parks Historic Sites

Side Trips

Plymouth, Lexington, Cape Cod Canal, Nantasket Beach
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Jenney Museum ©
Jenney Museum
Nantasket Beach ©
Nantasket Beach

1
night
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. On the 1st (Sun), contemplate the long history of Billings Farm & Museum, relax in the rural setting at Sugarbush Farm, and then explore the stunning scenery at Quechee Gorge.

To see ratings, traveler tips, more things to do, and tourist information, use the Woodstock trip site .

You can fly from Boston to Woodstock in 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Boston in August, plan for slightly colder nights in Woodstock, with lows around 56°F. Cap off your sightseeing on the 1st (Sun) early enough to go by car to Burlington.

Things to do in Woodstock

Historic Sites Museums Parks

Side Trip

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

1
night
Burlington

Burlington ©
Burlington is the most populous city in the U.S. On the 2nd (Mon), trek along Burlington Bike Path, then contemplate the long history of Ethan Allen Homestead, then contemplate the long history of Shelburne Farms, and finally sample the tasty concoctions at Magic Hat Brewing Company.

For traveler tips, more things to do, where to stay, and more tourist information, read our Burlington trip itinerary builder .

You can drive from Woodstock to Burlington in 2 hours. Alternatively, you can take a bus. Expect a daytime high around 75°F in September, and nighttime lows around 53°F. Finish your sightseeing early on the 2nd (Mon) to allow enough time to travel back home.

Things to do in Burlington

Trails Parks Outdoors

Side Trips

Magic Hat Brewing Company, Shelburne Farms
Highlights from your plan
Burlington Bike Path ©
Burlington Bike Path
Magic Hat Brewing Company ©
Magic Hat Brewing Company
Shelburne Farms ©
Shelburne Farms

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