Romantic Foliage Weekend in the Berkshires

Escape to the Berkshires this fall for a romantic foliage getaway filled with cozy inns, scenic drives, and unforgettable dining. Base yourself in Stockbridge or Lenox with a stay at the luxurious Blantyre or the historic Red Lion Inn, both offering classic New England charm. Drive the winding Jacob’s Ladder Scenic Byway, one of the most beautiful fall foliage routes in Massachusetts, before enjoying an intimate wine tasting at Les Trois Emme Winery. In the evening, savor a candlelit dinner at the Old Inn on the Green, where flickering light and seasonal cuisine set the mood. Add a sunrise hike at Laura’s Tower or Olivia’s Overlook for breathtaking views, and spend time strolling through the charming towns of Stockbridge and Lenox, with their boutique shops, historic streets, and small-town romance. This itinerary blends autumn scenery, fine dining, and timeless New England ambiance for the perfect couples’ getaway.