Romantic Getaways, Gifts, and Experiences in the Berkshires

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!

TOURISTS. Credit Great Sky Media.

Stay and Do

Enjoy a cozy weekend at the boutique Black Swan Inn on Laurel Lake or the Chambery Inn B&B, both in Lee and close to the Mass Turnpike, the Lee Premium Outlets, and the award-winning Canna Provisions cannabis dispensary. Presumably, you will be hungry after shopping and bud, and there are some great eats close by, including hearty tavern fare at 51 Park Restaurant or an elevated brunch (and/or cocktail) at the Dulu Cafe & Lounge. And since you are treating yourselves royally, do not miss Chocolate Springs Cafe in Lenox for a decadent hot chocolate and melt-in-your-mouth specialty chocolates like tangerine ginger, pistachio marzipan, and Paris tea.

Further north, TOURISTS in North Adams offers a classic motor lodge experience, including hiking, live music, crafts, yoga, and a cocktail lounge and cafe serving breakfast, snacks, and guest chef pop-ups. And it’s really close to MASS MoCA and iconic Mount Greylock, and Bright Ideas Brewing taphouse (try the Aztec Winter stout). After you’ve toured the vibrant exhibitions at The Clark museum — admission is free January-March 2025 and the grounds are incredible for snowshoeing — enjoy a massage and the outdoor hot tub at InTouch Day Spa in Williamstown. Perhaps there is something just between the two of you, a secret passion…for LEGOS®! Bottomless Bricks in Pittsfield will have your hearts pounding with new and pre-owned Harry Potter™, Ghostbusters, pirate, and train sets.

 Put yourself out there

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. 

 A rose, by any other name

We’ve covered chocolate, weed, and cozy spaces, but let’s not overlook one of the most romantic symbols of devotion: Flowers. The Berkshire region is overflowing with charming floral shops and garden centers that add an extra touch of beauty. Pryma Petals, a flower farm in Great Barrington, specializes in dahlias of all sizes and a selection of fresh blooms and unique floral arrangements. For a completely immersive flora experience, Ward’s Nursery & Garden Center, also in Great Barrington, has been a mecca of perennials, cacti, gifts, and great advice for nearly seven decades. Plan on spending a few hours there (which means, bring a hot drink). If you want to be enchanted by unique wreaths and gifts, Thistle ‘n Thorn on North Street in Pittsfield, offers arrangements, bouquets, and pop-up workshops onsite and around the county. Check out their Instagram for the latest offerings.  

Enjoy the cozy fires and glittering stars. And take inspiration from Edith Wharton, one of the region’s most famous residents and writers, “…you did love me for a moment; and it helped me. It has always helped me.”

 Sigh…

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