32 days in Brattleboro & Carlisle Itinerary

32 days in Brattleboro & Carlisle Itinerary

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Route & dates

32 days in Brattleboro & Carlisle Itinerary

Start: Washington DC
Fly + Drive:  6​h
— 15 nights
Drive:  6​h 15​min
— 16 nights
Drive:  2​h 15​min
End: Washington DC


Brattleboro ©
Brattleboro, originally Brattleborough, is a town in Windham County, Vermont, United States. Get out of town with these interesting Brattleboro side-trips: Deerfield (Historic Deerfield, Clarkdale Fruit Farms, & more), Charlemont (Bissell Covered Bridge & Zipline) and Manchester (Hildene, The Lincoln Family Home, North Meadow Farm, & more). There's lots more to do: experience rural life at Robb Family Farm, look for gifts at Delectable Mountain Cloth, browse the eclectic array of goods at Brattleboro Farmers' Market, and take in the views from Bridge of Flowers.

To find more things to do, where to stay, and more tourist information, refer to the Brattleboro visit site .

Washington DC to Brattleboro is an approximately 6-hour combination of flight and car. You can also drive. Traveling from Washington DC in September, things will get slightly colder in Brattleboro: highs are around 74°F and lows about 50°F. Finish your sightseeing early on the 21st (Sat) so you can travel to Carlisle.

Things to do in Brattleboro

Parks Nature Outdoors

Side Trips

Peterborough, Manchester, Deerfield, Charlemont, Petersham
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Hildene, The Lincoln Family Home ©
Robb Family Farm ©
Robb Family Farm
Saxtons  Distillery ©
Saxtons Distillery


Carlisle ©
Carlisle is a borough and the county seat of Cumberland County, Pennsylvania, United States. Change things up with these side-trips from Carlisle: Jan Zell Wines (in Chambersburg), Antietam National Battlefield (in Sharpsburg) and Gettysburg (Abraham Lincoln Statue, David Wills House, & more). Next up on the itinerary: learn about all things military at United States Army Heritage and Education Center (USAHEC), gain insight at Penn State University, stop by Castlerigg Wine Shop, and immerse yourself in nature at Kings Gap Environmental Education and Training Center.

To see reviews, traveler tips, other places to visit, and tourist information, read Carlisle trip itinerary tool .

You can drive from Brattleboro to Carlisle in 6.5 hours. Another option is to do a combination of car and flight. Traveling from Brattleboro in September, Carlisle is a bit warmer at night with lows of 59°F. Finish up your sightseeing early on the 7th (Mon) so you can travel back home.

Things to do in Carlisle

Museums Historic Sites Parks

Side Trips

Gettysburg, Winchester, State College, Berkeley Springs, Altoona
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