★ 4.0Positioned in the southeast corner bordering Massachusetts.
The counterculture river town of Brattleboro, two big ski mountains and some of the state’s prettiest greens.
Where to stay in Windham County
Brattleboro is the base for anyone who wants to walk to dinner, arrive by train and pay the least, but it is a good forty minutes from Mount Snow by VT-9 and VT-100, a drive that gets serious over Hogback in snow. Skiers should choose between West Dover, closest to the Mount Snow lifts, and Wilmington ten minutes down VT-100, which has more of a village and slightly softer rates; for Stratton the equivalent trade is the resort village itself against Bondville and the VT-30 corridor below it. In summer and autumn the prettiest bases are the VT-30 and VT-35 villages, Newfane, Townshend and Grafton, where you swap shops and restaurants for greens and quiet. Winter weekends and the first two weeks of October are what you book far ahead; midweek, almost everything is open to you.
Hand-checked stays
Stays in Windham County
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★ 4.0On the ground
Things to do in Windham County
- Brattleboro Gallery WalkA lively arts town on the Connecticut River — galleries, a co-op and a first-Friday art walk.
- Mount Snow & StrattonTwo of southern Vermont’s biggest ski resorts, closest to the Boston and New York crowds.
- GraftonA meticulously preserved 19th-century village with a still-working cheese company.
- Newfane greenA classic white-clapboard common with a county courthouse and nearby covered bridges.
Getting around & the essentials
Transport
I-91 runs north from the Massachusetts border through Brattleboro and Bellows Falls, with VT-9 crossing west to Bennington, VT-30 following the West River valley and VT-100 serving Wilmington and Mount Snow. The Amtrak Vermonter stops at Brattleboro and Bellows Falls, and the nearest airports are Bradley near Hartford at about 90 minutes and Boston Logan at roughly two hours; a car is needed for anything beyond the two river towns.
Good to know
Common questions
How do I get to Windham County from the south?
I-91 runs the length of the county from the Massachusetts line, putting Brattleboro roughly two hours from Boston and four from New York City. The Amtrak Vermonter also stops at both Brattleboro and Bellows Falls.
Which ski mountain suits a family better?
Mount Snow is closer to Brattleboro and I-91 and generally the easier drive, while Stratton is a longer haul up but a larger, more self-contained resort village. Both fill on winter weekends, so mid-week is dramatically calmer and cheaper.
What is there to do in summer?
Swimming and paddling on the West River and Harriman Reservoir, hiking in Townshend and Jamaica state parks, chamber music at Marlboro, and village hopping along VT-30 and VT-35. Rates outside ski season are the lowest of the year.
Is the county walkable anywhere?
Brattleboro and Bellows Falls both have compact, walkable downtowns, and the resort villages at Mount Snow and Stratton work on foot once you have arrived. Everywhere else assumes a car.
Keep exploring
Nearby towns
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