This Charming Mountainous Destination In New England Is Perfect For A Romantic Getaway

Set in the rolling hills of western Massachusetts, the Berkshires offer the kind of small-town charm and natural beauty that feels tailor-made for a romantic escape. This picturesque region of New England combines mountain views, farm-to-table dining, and cozy B&Bs, making it an ideal place for couples to slow down and reconnect. And as the Berkshires are only a two-hour drive from Boston and 2.5 hours from New York City, the region is easily accessible, but just far enough to feel like you're getting away from it all. 

While New England is often associated with the fiery reds and oranges of fall foliage, the Berkshires are a year-round destination. Autumn might bring a New England fall road trip, complete with pumpkin patches, apple stands, and hot cider. In the winter, you can enjoy quirky winter activities in Stockbridge before snuggling up by the fire after an invigorating walk in the chilly air. Come spring, fresh maple syrup drips off the trees, and in summer, it's time to experience the magic of outdoor theater under the stars.

No matter your vibe, the Berkshires have something for everyone. Outdoorsy pairs are spoilt for choice by the hikes on offer. You might choose the fairly short stroll out to Bash Bish Falls, the highest waterfall in Massachusetts, which cascades 60 feet into the pristine pool below. Head out early to avoid the crowds and enjoy a more romantic experience. If you're up for something more strenuous, tackle Mount Greylock, the highest peak in the state at almost 3,500 feet. Several routes up vary in difficulty; check AllTrails to find the one that suits you best.

For the perfect base to an artsy couple's trip to the Berkshires, choose the charming town of Lenox, especially if you're visiting in the summer. It's home to the Arthur S. Waldstein Amphitheatre, where the Shakespeare & Company group performs many of the Bard's plays in the open air. Is there anything more romantic than watching "Romeo and Juliet" under the stars? Also in Lenox is Tanglewood, the summer home of the Boston Symphony Orchestra. A picnic on the lawn outside the Shed, where performances take place, is a must-do in the Berkshires.

The beauty of the area has long drawn creatives. In Lenox, you can wander through The Mount, the former home of Edith Wharton and now a museum. Over in Stockbridge, the Norman Rockwell Museum holds almost 1,000 works by the great American artist. And up in Pittsfield, Arrowhead allows you to discover where Herman Melville wrote "Moby Dick."

During the day, visit a farm to try some local produce. High Lawn Farm in Lee specializes in dairy products; order a charcuterie board to eat at one of the picnic tables and finish off with fresh ice cream. In the fall, they have a pumpkin patch, hot cider, and fall-flavored ice creams! If you're in the Berkshires in spring, Maple Corner Farm in Granville serves a pancake breakfast, drizzled with their own pure maple syrup.

For dinner, Cello in Lenox offers a romantic, intimate experience, with dishes praised in reviews as "exquisite" and "phenomenal." Also in Lenox, Alta serves Mediterranean-inspired cuisine and features an extensive wine and cocktail list. Don't miss the local Berkshire bourbon and rum.

Finally, an essential part of planning a couple's getaway is finding somewhere suitably charming and romantic to stay. Cozy inns and bed and breakfasts are scattered throughout the Berkshires. A few of our picks in Lenox include the Hampton Terrace Inn, which invites you to step back in time to the Gilded Age, with its period-style rooms, some complete with a fireplace. At the grandly decorated Cornell Inn, the breakfasts get rave reviews. Or, for a truly luxurious getaway, couples might head to Miraval Berkshires Resort and Spa, where a 29,000-square-foot spa, three swimming pools, and a mindfulness center create the perfect setting for a wellness retreat.