The air is crisp, the leaves are turning, and Vermont is settling into one of its most beloved seasons. Fall in Bennington is a time for scenic drives, apple picking, warm drinks, and community traditions that bring everyone together. Whether you’re planning a romantic weekend escape, a family adventure, or simply looking for a reason to explore, October in Bennington has something for you.

Chasing Foliage & Outdoor Adventures

Bennington is a natural hub for fall color, sitting at the crossroads of Vermont, New York, and Massachusetts. By early October, drives along Route 7 from Massachusetts or Route 9 from New York and Vermont’s North Country glow with maples and birches. For the best views, make time for a stop at the Bennington Battle Monument or stroll the outdoor trails at the Benn

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