10 Great

After Dark: Adventures for Couples

By Nancy Macy

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 cold winter night.

Enjoy the outdoors together.

Photo Credit Ogden Gigli

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, 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.

For wintry outdoor adventures, try downhill skiing under the stars at Jiminy Peak, Catamount, and Berkshire East; or tubing under the night skiing at Bousquet. Glide hand-in-hand across the ice-skating rinks at Cranwell Spa & Golf Resort and Blantyre or explore their groomed trails on cross-country skis or snowshoes. Visit Hilltop Orchards at Furnace Brook Winery for a guided full moon nature hike followed by a bonfire, live entertainment, and wine tasting. Or combine a cross-country or snowshoe trek with a Brew Moon beer-tasting event at Notchview.

Couples can enjoy the region’s cultural arts scene with evening lectures, films and art classes at The Clark and the IS183 Art School. 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 MASS MoCA in North Adams.

Stay at a romantic spot.

Location: The Gateway 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 Firefly Gastropub & Catering Co., 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. If you are looking for some live music combined with a cocktail be sure to stop in at The Gateways Inn lounge.

For a more intimate shared experience, book a weekend retreat package at Canyon Ranch 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!


Nancy Macy is a freelance writer and editor based in the Berkshires.