Why October Is a Glorious Time to Get Away to the Berkshires

There’s something special about the way October wraps itself around the Berkshires. The air turns crisp, the hillsides glow in gold and crimson, and time seems to slow down—inviting you to breathe, wander, and rediscover what it means to relax.

At The Red Lion Inn, autumn is more than a season—it’s a feeling. It’s the quiet joy of a morning coffee on the front porch, the satisfying crunch of leaves underfoot, and the cozy comfort of a fireside evening with a glass of local cider in hand.

The Perfect Time for a Fall Escape

While summer in the Berkshires brings outdoor concerts and garden strolls, October offers a more peaceful kind of magic. The crowds have thinned, the colors are at their peak, and our charming village of Stockbridge feels like it’s been painted just for you.

It’s the perfect time to explore the Norman Rockwell Museum, take a scenic drive down Route 7, or wander through Naumkeag’s Pumpkin Show before returning to the Inn for hearty fare in the Main Dining Room or a nightcap in the Lion’s Den.

Cozy Comforts Await

Each of our rooms offers a retreat from the bustle of everyday life—filled with history, warmth, and the timeless hospitality that has defined us since 1773. Curl up by the fire, savor a seasonal cocktail, or simply take in the view from your window as the village glows in autumn light.

Make It a Tradition

Whether it’s a romantic weekend, a family getaway, or a spontaneous solo escape, October is the perfect month to make The Red Lion Inn part of your fall tradition. It’s when the Berkshires show their truest colors—and when the Inn feels most like home.

So pack your sweater, bring your sense of wonder, and come see why October truly is the best time to get away.