Food & Drink Weekend in the Berkshires

Savor the flavors of fall in the Berkshires with a culinary-focused weekend that highlights the region’s best farm-to-table dining, wineries, cider houses, and local markets. Start your trip with brunch at beloved cafés like Haven Café & Bakeryor Six Depot Roastery, then spend your afternoons wine tasting at Balderdash Cellars, sampling cider at Hilltop Orchards, or enjoying craft cocktails and small-batch spirits at Berkshire Mountain Distillers. Evenings are reserved for memorable meals at acclaimed restaurants such as Prairie Whale, Cantina 229, and Alta Restaurant & Wine Bar, where menus showcase fresh, seasonal ingredients. Along the way, stop at farm stands and pumpkin patches for true autumn flavors, from cider donuts to harvest produce. With cozy stays at the Apple Tree Inn in Lenox or the historic Red Lion Inn in Stockbridge, this itinerary blends world-class dining with rustic New England charm — the perfect way to experience the Berkshires in fall.