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Adventures for Couples

Posted on September 07, 2022Written by Nancy Macy
Updated on September 20, 2023

Two women toast with glasses of wine at Balderdash Cellars in the Berkshires. Photo by Kacey Hatch.

Book a Cozy Getaway this Fall & Winter in the Berkshires

Just a few hours from the bustling urban landscapes of Boston and New York City, the Berkshires offers spectacular scenery, outdoor recreation, world-class cultural arts, and a thriving artisanal food scene. It’s the perfect place for sparking some heartwarming romance with your special someone, especially on a chilly fall day or cold winter night.

A couple hikes at Mount Greylock. Photo by Kacey Hatch.

Whether you’re just getting acquainted with each other or are spending kid-free time together to reconnect, the Berkshires offer plenty of romantic nighttime activities. Candlelit dinners, colorful leaf peeping, moonlit cross-country skiing, and winding down with a couples massage are just a few of the many options for creating a memorable weekend getaway or date night.

This fall, visit one of our many orchards, like Hilltop Orchards and Bartlett’s, to stroll through apple trees together, then sip cider at Berkshire Cider Project or a glass of wine with a view at Balderdash Cellars. For wintry outdoor adventures, try downhill skiing or tubing at Jiminy Peak, Catamount, Berkshire East, or Bousquet. Glide hand-in-hand across the ice on a frozen lake or Notchview or Maple Corner Farm on cross-country skis or snowshoes. Afterward, warm up with a wine tasting at Les Trois Emme Vineyard & Winery.

A couple enjoys the snow in the Berkshires. Photo by Ogden Gigli.

Couples can enjoy the region’s cultural arts scene with evening lectures and films at The Clark. Shop for handmade wares at Shaker Mercantile, ROAM, and Hoogs and Crawford Glass. The Berkshire Theatre Group winter season brings comedy, music, and theater shows to the Colonial Theatre in Pittsfield. Date-worthy events are also scheduled at the Mahaiwe in Great Barrington and if you are looking for some excellent cocktails with live, be sure to stop in at the Apple Tree Inn.

Looking to share a great meal or a delicious drink? You’ll find everything from casual fare to fine dining in the Berkshires. Book a dinner reservation for an inspired meal prepared by one of the area’s renowned chefs. Get a taste of Berkshire-made microbrews and distilled spirits at a cozy pub or tavern. Sip craft cocktails made by some of the region’s most creative mixologists found at eateries such as Methuselah Bar and Lounge and District Kitchen & Bar. Nibble on noshes and tapas as you discover a new favorite wine from the extensive selection at Brava.

For a more intimate shared experience, book a weekend retreat package at Miraval, blu Salon & Spa, or Brook Farm Inn. Schedule an evening spa service together to cap off a day of adventure. Find a crackling fireplace and cuddle up. Stroll the grounds during a gentle snowfall, snowflakes swirling in the glowing lights along your path. Turn off your cell phones, and turn up the romance factor.

In addition to the low-key vibe and warm hospitality here, you’ll find interesting and memorable ways to rekindle (or kindle) your romantic flame. Spend time with someone special in the Berkshires this winter and you’ll see what we mean!

Looking for more inspo? Explore places to stay, where to eat and drink, and things to do!

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