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Living a Mountain Lifestyle in Brattleboro, Vermont

Nearby skiing is excellent at Mt. Snow, Stratton Mountain, Bromley, and Okemo – just to mention a few. This small city along the Connecticut River in southern Vermont has an artsy ambience. Brattleboro, Vermont (population 12,000) is an interesting mountain community for those who love the outdoors. Although it has many who embrace its wintery climate, many others only live here during the warmer months. The downtown situated close to the river bank is bustling. The lack of level land has created a situation where houses are built on steep slopes, leading to an interesting and urban atmosphere. The financial structure is well supported by a number of motels, retail businesses and a large medical facility – the Brattleboro Retreat. There are some stately homes in Brattleboro.

The city has an unusual combination of flavors - it exudes a bit of 70’s counterculture (the Brattleboro Food Cooperative is one of the biggest cooperatives in New England) and a more sophisticated side as well. Many wealthy New Yorkers weekend here for the skiing and or the mild summer weather. Hiking, camping, and other outdoor adventures in the surrounding mountains is also first rate. The lake in town normally offers excellent ice fishing.

Where to Retire in Brattleboro and Home Prices

The housing choices for retirees are somewhat limited in town, mostly in the form of private homes or mobile homes. Prices are a relative bargain compared to other parts of New England. Many retirees choose to live closer to one of the big ski resorts and use Brattleboro for shopping. These resorts have a large array of condos and homes. According to Zillow, the median home value in Brattleboro was $298,089 in early 2023.

What Is Special about Brattleboro

Counterculture feel - Interesting downtown - A livable small city - Listed as one of the top 10 Art Towns (smaller cities) - Interesting restaurants - Gateway to the mountains and many excellent ski resorts - Annual Brattleboro Literary Festival

What Is Not Special about Brattleboro

Winters are long, cold, and dark, unless you love winter sports! The northern part of town is not very appealing with its endless strip malls and motels.

Climate and Physical Environment

Brattleboro is located in the Connecticut River Valley. To the west, east, and north an extensive chain of hills and mountains rise up, including the Green Mountains.

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Restaurants & Cultural Scene

Annual Brattleboro Literary Festival. Many famous people in the arts have lived here; Saul Bellow is buried here. The New England Youth Theatre, Brattleboro Film Society, many art galleries, the Vermont Theatre Company.  Gallery Walk is held on the first Friday of every month, in which galleries, artists, and arts organizations open their doors to the public to display new work or hold performances. Included in the organizations that participate are the Brattleboro Museum and Art Center, the Hooker-Dunham Theater and Gallery, and the In-Sight Photography Project.


The crime rate is slightly above average.

Medical Facilities

Brattleboro Memorial Hospital Brattleboro Retreat


Bradley International Airport is about 50 miles (Hartford/Springfield) Amtrak has a station here the "Vermonter" train arrives daily between Washington, D.C. and St. Albans, Vt. The Moover is the ubiquitous and useful local bus system.

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