Romance in the Berkshires

With its beautiful views and whimsical culture, the Berkshires is the perfect spot for a Valentine’s Day (or just plain romantic) winter getaway. 

Our curated list of amorous things to do in the Berkshires includes weekend escapes and day trips perfect for sweethearts—whether your idea of romance is a snow-covered outdoor adventure, a spa getaway, or a daylong cultural excursion exploring world-class museums, quirky shops, and farm-to-table restaurants, the Berkshires is truly a place for lovers!

Where to Stay

Plan an intimate weekend at the Blue Vista Motor Lodge nestled on the Mohawk Trail , the rustic Race Brook Lodge in Sheffield that also offers candlelit dining in the historic Stagecoach Tavern, or the eclectic Apple Tree Inn in Lenox. Or take advantage of a winter special at The Guest House at Field Farm, a 1948 Bauhaus-inspired house situated on 316 acres of conservation land. Each property has its own unique flavor, from vintage-kitsch to historic haven, and provides a cozy landing pad after exploring the iconic Berkshire sights and venues.

What to Do

Outdoor enthusiasts can hit the slopes at our many premier ski resorts. Enjoy skiing and tubing at the historic Berkshire East Mountain Resort in Charlemont, cross-country skiing at Notchview, snowshoeing (and wine and cider tasting) on the 200-acre Hilltop Orchards, or hiking at any one of the region’s network of trails and vistas.  Art lovers can explore independent galleries in nearly every town as well as  world-class museums including The Clark, MASS MoCA, and the Norman Rockwell Museum. Wellness seekers can book a spa day or resort weekend (couple’s massage, anyone?) at the award-winning Miraval Berkshires or a restorative retreat at Kripalu Center for Yoga & Health. Because ideas of wellness differ from person to person, perhaps your ideal R&R can be found at the innovative Theory Wellness cannabis dispensary featuring a wide variety of flower, concentrates, and infused products.

Where to Eat (and Drink)

Outdoor fire pits, big barns twinkling with lights, and historic wood-paneled pubs with stone fireplaces abound at the many restaurants, pubs, and tasting spots in the Berkshires. Take in the views and the vintage at Balderdash Cellars in Richmond or enjoy an earthy flight of small-batch spirits at the Berkshire Mountain Distillers on the Route 7 corridor in Sheffield. Food is the way to anyone’s heart, so if your romantic trip centers around Valentine’s Day, make a candlelit dinner date at The Old Inn on the Green (a former stagecoach stop in the village of New Marlborough), explore craft beers and farm-forward fare at District Kitchen & Bar in Downtown Pittsfield, or plan a stop at Mint Indian Lakeside in Lee, whose Sunday lunch buffet has a local cult following. 

Amidst all of these unique offerings and venues is the everlasting, romantic backdrop of a sought-after place revered by artists, authors, and explorers. As Nathaniel Hawthorne wrote nearly 200 years ago, “The sunsets of winter are incomparably splendid, and when the ground is covered with snow….. our southern view…. with the clouds and atmospherically hues, is quite indescribable and unimaginable.”

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