Perched at the confluence of the Connecticut and West Rivers, Brattleboro is a little gem that reveals its facets to those who stroll the streets and prowl the dozens of independent shops and eateries. An energetic mix of aging hippies and the latest crop of pierced and tattooed hipsters fuels the town’s sophisticated eclecticism, keeping the downtown scene percolating and skewing its politics decidedly leftward.
The Whetstone Brook runs through the south end of town, where a wooden stockade dubbed Fort Dummer was built to defend Vermont’s first Colonial settlement (1724) against Native Americans. The town received its royal charter a year later, named for Colonel William Brattle Jr of the King’s Militia, who never set foot in his namesake.
At the Old Town Hall (location of the current Main Street Gallery), many celebrated thinkers and entertainers held forth on the concerns of the day, including Oliver Wendell Holmes, Horace Greeley and Will Rogers. Rudyard Kipling married a Brattleboro woman in 1892, and while living here he wrote The Jungle Book.