From the lowlands of the Connecticut River Valley to the famous rolling mountains—OK, hills—of the Berkshires, Western Massachusetts is an attractive destination for a weekend getaway. Small towns sprinkled throughout the region offer homemade ice cream, country stores, and scenic rural drives, as well as picturesque colleges and spas.
In the winter, skiers flock to the mountains, while the summer months light up with cultural events, consistently garnering big names and rave reviews. Both modern and traditional, the area brings an amazing assortment of theater, music, contemporary art, and outdoor adventure within an easy drive of Boston and New York City.
Check out our guide to three great towns that make the best weekend getaways in Western Massachusetts.
1. Pioneer Valley
Pioneer Valley, also known as the Five College Area, has all the best attributes of a college town: cute and cheap restaurants and cafes, impressive museums, and plenty of bike trails and parks to relieve the stress of a liberal arts education. The peak visiting season is in the fall, when tourists come to marvel at the foliage and share in the bounty of the harvest at roadside produce stands.
Aside from aggressive tourism, the best way to keep offbeat shops and eateries afloat is to pack the surrounding square miles with college students. With nearly 30,000 of them, Pioneer Valley does just that. Preppy Amherst College, freewheeling Hampshire College, all-female Mount Holyoke College, liberated Smith College, and the gigantic University of Massachusetts at Amherst make up the Five College Consortium.
Emily Dickinson Museum
Address: 280 Main Street, Amherst, MA 01002
The Emily Dickinson Museum is five minutes down the road from Amherst town center. It’s the birthplace of the 19th-century poet, whose poems were discovered in her bedroom after her death. The museum opened in 2003 and is dedicated to educating the public about Dickinson’s life, family, work, and relevance.
2. North Adams
In its heyday as a large industrial center, North Adams had 100 trains passing through the Hoosac Tunnel each day. Over time, the factories changed into art studios and galleries—some of the best in New England—and today, modern art stands where assembly lines and machinery once loomed.
Clarksburg State Park
Address: 1199 Middle Road, Clarksburg, MA 01247
Clarksburg State Park is just few miles north of town but makes you feel like you’re a million miles away. With 45 campsites along Mauserts Pond and 368 acres of woods, water, and hiking trails, this scenic park offers beautiful views of the Berkshire Hills and the Green Mountains.
Address: 1040 Mass MoCA Way, North Adams, MA 01247
The Massachusetts Museum of Contemporary Art (Mass MoCA) has galleries in 26 old factory buildings and is the largest center for contemporary arts in the country. Pushing the envelope of modern art, the museum houses upside-down trees, large multimedia displays, and fascinating rotating exhibits.
Western Gateway Heritage State Park
Address: 115 State Street, Building 4, North Adams, MA 01247
Just after the Hadley Overpass off Route 8, this state park celebrates the history of the Hoosac Tunnel. While you’re in the area, head half a mile north along Route 8 to Natural Bridge State Park on McCauley Road for a look at North America’s only natural white marble arch. Navigate the labyrinth of stairs and stone leading to the bridge or pack a picnic to enjoy on the grounds.
Williamstown, a cozy town on the Vermont border, is home to Williams College, the second-oldest college in Massachusetts.
Norman Rockwell Museum
Address: 9 Glendale Road, Stockbridge, MA 01262
Enjoy some old-fashioned Americana at the Norman Rockwell Museum, where you can visit the artist’s studio and the largest single collection of his original works, including many Saturday Evening Post covers.
Address: 3 Williamsville Road, Stockbridge, MA 01262
Just down the road lies Chesterwood, the home and studio of sculptor Daniel Chester French of Lincoln Memorial fame. The 150-acre estate operates as a museum and sculpture garden, displaying Chester’s work as one of the leading sculptors of his era. The grounds also include walking trails, a picnic area, and hands-on activities for kids.
Berkshire Botanical Gardens
Address: 5 West Stockbridge Road, Stockbridge, MA 01262
Enjoy fresh fragrances and stunning flower arrangements at the Berkshire Botanical Gardens. The 15-acre grounds are home to over 3,000 species and varieties of plants and offer walking trails, three greenhouses, and an education center.
Address: 5 Prospect Hill Road, Stockbridge, MA 01262
Set in the rolling hills overlooking Stockbridge, Naumkeag is the 44-room Choate family mansion surrounded by lavish gardens, a blue-roofed Chinese temple, and perfectly manicured trees. The property was bequeathed in its entirety in 1958, including everything from the original furniture to garden tools, and offers a unique and interesting look at the history of the Berkshires and surrounding area.