Discover the Dreamy Charm of Hampshire County, Massachusetts

In the western half of Massachusetts, where rural and cosmopolitan coexist, lies the dreamy and sophisticated Hampshire County. City living meets homesteading in this charming slice of New England, where you can sip a Gimlet, dine on creative cuisine, and pick your own organic peaches. In one weekend, you can explore world-class museums, rock local music scenes, shop bustling downtowns, and hike to the peak of a mountain. With so much to do and see, Hampshire County has everything you could want from a weekend away.

ESCAPE TO THE CITY

The cities of Hampshire County boast vibrant, intellectual hubs full of things to do, see, and learn. Take in the youthful and lively downtown core of Amherst by stopping by the independent movie theater, the bookstores set against the backdrop of historical architecture and blooming flower gardens, and diverse restaurants, cafes, and art galleries. Grab dinner at the newly opened Amherst Oyster Bar, then cross the street to catch an intimate concert—jazz, indie, and more at The Drake.

Late-night bites, fancy cocktails, and music await in the hidden gems of Northampton, known for being exceptionally LGBTQ-friendly and welcoming. Let the rainbow-painted crosswalk be your guide to Northampton’s eclectic downtown, home to boutique shops and 100+ locally owned restaurants, pubs, chocolatiers, and eateries.

Over in cozy Easthampton, farmers’ markets brim with local bounty year-round, and there are always new coffee shops, galleries, and bookstores to explore. When the sun goes down, you’ll find live theater, music, and more at CitySpace, Marigold Theater, and Luthier’s Co-op.

Ready for some quiet time? Explore the Arcadia Wildlife Sanctuary, just minutes away from downtown along the bike-friendly Manhan Rail Trail.

Art and music lovers will be inspired by the many museums, theaters, and galleries—catch a show at the Academy of Music Theatre in Northampton or the Bombyx Center for Arts & Equity in nearby Florence. The Eric Carle Museum of Picture Book Art in Amherst and the Smith College Museum of Art offer up visual delights, while Amherst College is home to the Beneski Museum of Natural History and the Mead Art Museum, both of which boast must-see collections for art and history lovers alike.

Downloadable itineraries for the Hampshire County Museum Trail make planning your visit even easier.

SUMMER IN NEW ENGLAND

When the sun comes out and the weather warms up, Northampton’s Strong Avenue is the place to be. Each year, the street is transformed into a pedestrian-only oasis: Summer on Strong. From May to October, you can dine outdoors, stroll the shops, dance in the street, and celebrate the vibrant community, all while local artists play live music—the soundtrack of the summer.

Don’t miss the Paradise City Arts Festival either—the last weekend of May brings out the best of Northampton’s visual arts scene. From craftspeople and fine artists to sculptors and fashion designers, this festival brings together hundreds of specially selected artists and makers for three days of celebrating art, design, food, and music.

As summer turns to fall, join in on the fun at Millpond Live’s festival weekends, packed to the brim with entertainment, music, art, and mouth-watering local eats. Or cool off while you enjoy a cocktail and a lazy riverboat cruise on The Lady Bea, launching out of Brunelle’s Marina in South Hadley—stick around afterward for a delicious waterfront dinner while the sun sets over the rippling Connecticut River.

Of course, no summer would be complete without indulging in farm-fresh fruit picked at your own pace while you enjoy the sunshine. Hampshire County is home to a variety of pick-your-own farms—Phoenix Fruit Farm, for example, is a scenic 103-acre farm just a short drive from Amherst. Take the family along for a pick-your-own adventure with the choice of fresh apples, peaches, and strawberries. The farm is pesticide-free, too, so feel free to sample the fruits of your labor on the way home!

Want to let someone else do the work? Stop into Florence Pie Bar, named one Yankee Magazine’s top 5 pie shops in New England (and the only one from Massachusetts) to sample a dizzying selection of delectable treats.

For an artsy take on pick-your-own fun, head to Easthampton’s Park Hill Orchard and stroll through their self-guided walking sculpture trail, surrounded by endless rows of flavorful tree-ripe fruit. Make an afternoon of it by bringing a picnic basket and spending some time lounging amongst the trees. Be sure to hit up the farm store before you leave—the Cider Slushie is a seasonal staple too good to miss.

MAKE YOURSELF AT HOME

When the day is done, Hampshire County has no shortage of cozy places to lay your head. The Inn on Boltwood in Amherst—turning 100 this year—features stylish, modern guest rooms, wrapped in the historic original architecture for a classic New England experience. Enjoy a nightcap by the rooftop fireplace, or stroll downtown Amherst, just steps from the front door.

Or book a room at The Old Mill Inn in Hatfield, where you’ll fall asleep to the sound of a waterfall outside your window. Visiting with your bike in tow? Check out the Sugar Maple Trailside Inn, a B&B located on a stretch of Hampshire County’s expansive rail trail network.