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The Best Places for Romance in the Berkshires

Posted on January 11, 2023Written by Nancy Macy on behalf of 1Berkshire
Updated on December 05, 2023

Red Lion Inn tavern restaurant couple dining year round

Discover a Valentine’s Day you’ll never forget with our useful romantic spots guide

No matter how long you’ve been a couple, there’s nothing like creating lasting memories together to deepen your bond. Our list of romantic things to do in the Berkshires includes weekend escapes and day trips perfect for sweethearts—whether your idea of shared bliss is an outdoor adventure, spa getaway, or exploring museums, shops, and great restaurants.

Some of the most beautiful places in the Berkshires are also the perfect spots for a Valentine’s Day getaway. Plan an intimate weekend for two at The Porches Inn in North Adams, 33 Main in Lenox, or Old Inn on the Green in New Marlborough. All are distinctive historic properties reimagined with modern amenities, located not far from all the activities you enjoy together.

What is there to do on a romantic weekend in the Berkshires? Outdoorsy couples can hit the slopes at our premier ski resorts, cross-country ski on groomed trails at Ski Butternut or Notchview, snowshoe on the 140-acre campus of Clark Art Institute, or try hiking a Berkshire Natural Resources property. Art lovers can explore galleries and world-class museums like MASS MoCA or Norman Rockwell Museum. Wellness seekers can book a spa day (couple’s massage, anyone?) at Miraval Berkshires or a weekend retreat at Kripalu Center for Yoga & Health of Canyon Ranch. With the abundance of award-winning farm-to-table restaurants serving the fresh flavors of the Berkshires, foodies have plenty of options for sharing a plate of something delicious.

For a memorable Valentine’s date night in the Berkshires, start with an early dinner, then head for ‘Shakespeare in Love’ at Mahaiwe Performing Arts Center or stroll arm-in-arm through one of our picturesque downtowns. Some of the most-loved cozy and romantic restaurants in the Berkshires are John Andrews Farmhouse Restaurant in North Egremont and Prairie Whale in Great Barrington. In the mood for a nightcap? Try a glass of wine or spirit from a local vineyard or small-batch distillery served at a popular nightspot like the Lion’s Den in Stockbridge or Brava in Lenox.

Whether you’re planning a whole weekend or just a day together, the Berkshires has everything you need for the best romantic dates ever! Find more inspiration for your Valentine’s Day in the Berkshires by exploring places to stay, where to enjoy food and drinks, and more amazing things to do.

Photo Credits: Red Lion Inn; Mount Greylock, credit Kacey Hatch

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