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I’ve Visited the Berkshires for 15+ Years—This Charming Mountain Town Is One of My Favorites

Summary by Travel + Leisure
There’s much to love about this place.A view of Main Street in downtown Great Barrington, Massachusetts.Credit: Patrick Donovan/Getty ImagesKey PointsGreat Barrington combines classic Berkshires scenery with a walkable downtown full of independent shops, restaurants, galleries, and cultural attractions.Visitors can hike Monument Mountain, visit local farms, swim or paddle at Lake Mansfield, and ski nearby in winter.Farm-to-table restaurants and …

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I’ve Visited the Berkshires for 15+ Years—This Charming Mountain Town Is One of My Favorites

There’s much to love about this place.A view of Main Street in downtown Great Barrington, Massachusetts.Credit: Patrick Donovan/Getty ImagesKey PointsGreat Barrington combines classic Berkshires scenery with a walkable downtown full of independent shops, restaurants, galleries, and cultural attractions.Visitors can hike Monument Mountain, visit local farms, swim or paddle at Lake Mansfield, and ski nearby in winter.Farm-to-table restaurants and …

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Travel + Leisure broke the news on Thursday, September 24, 2026.
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