Western Massachusetts Highlights: Family Fun, Stunning Landscapes and Beyond

New England’s first scenic road, the Mohawk Trail extends over 100 kilometers from the Connecticut River Valley to the Berkshire mountains of Western Massachusetts. Today, the cities and towns along this route offer unique opportunities to get immersed in cultural attractions and beautiful outdoor vistas. A variety of driving tours along the trail lead to historical highlights that include the Susan B. Anthony Birthplace Museum and a statue of the women’s suffrage activist at the Town Commons in nearby Adams, as well as Historic Deerfield, a preserved 18th-century colonial village. In Williamstown, discover the collections of two fine-art institutions: The Clark Art Institute is known for works by French Impressionists and Old Masters, while Williams College Museum of Art showcases an ever-growing body of more than 15,000 works. For outdoor experiences along the Mohawk Trail, don’t miss whitewater rafting on the Deerfield River, ziplining through the treetops of the Deerfield River Valley and cross-country skiing and snowmobiling in Monroe State Forest.

Located just three hours from both New York City and Boston, Berkshire County’s picturesque mountain landscapes have long been a haven for year-round outdoor adventurers and artists alike. Explore the hiking and biking trails of Mount Greylock State Reservation near Adams and Olivia's Overlook in West Stockbridge, then enjoy views of the mountains from the peace of your kayak or canoe on a paddling excursion on serene lakes. Come winter, Massachusetts’ largest ski area Jiminy Peak offers daytime and night skiing as well as lessons for all ages. Add culture to your itinerary with visits to the Massachusetts Museum of Contemporary Art (known as MoCA) in North Adams and the Norman Rockwell Museum in Stockbridge. Don’t miss the chance to see the Boston Symphony Orchestra’s summertime performances at Tanglewood and catch award-winning performances at Barrington Stage Company in Pittsfield. For a peek into the past, tour historic Gilded Age homes, including Chesterwood and Naumkeag in Stockbridge and Ventfort Hall and The Mount in nearby Lenox.

What do basketball, Yankee Candles and the Cat in the Hat have in common? They were all invented near the city of Springfield, in a metropolitan area locals know simply as Western Mass. Commemorate this heritage at sites like the Naismith Basketball Hall of Fame, whose hands-on exhibits explore the sport’s rich history, and Symphony Hall, whose Greek Revival- style auditorium has been hosting world-class performances since the early 1900s. Downtown, The Springfield Museums bring together art, history and science in a collection of five experiences all accessible for a single admission price; check out the Amazing World of Dr. Seuss Museum and the Springfield Science Museum, among other highlights. Get out in nature at the Northfield Mountain Recreation and Environmental Center, where the Rose Ledge and Hidden Quarry trails welcome hikers in the warmer months and snowshoe trails lend themselves to ski lessons in the winter. Interpretive cruises down scenic stretches of the Connecticut River show off even more local beauty.

The idyllic landscapes and youthful vibes of the Pioneer Valley make the perfect backdrop for some seriously unforgettable group outings. Country living meets city amenities throughout Hampshire County, from wagon rides at McCray’s Farm in South Hadley and you-pick fruit during summer and fall at Park Hill Orchard in Easthampton, to the vibrant downtowns of Northampton and Amherst peppered with local boutiques, cafés and inns. The Drake is a live-music staple featuring local, national and global acts in Amherst, while the Beneski Museum of Natural History boasts an extraordinary collection of specimens ranging from fossil skeletons to dinosaur footprints. In Florence, take a walking tour of the African American Heritage Trail starting at the Sojourner Truth Memorial Statue, which honors the famed abolitionist. Nearby, there’s year-round entertainment for everyone at Look Park. Stroll a family-friendly walking path with covered bridges and views of Willow Lake and see animals at Christenson Wildlife Center.

Discover unexpected delights in the hip and friendly towns around Franklin County. Thanks to a thriving and creative craft beverage scene, there are plenty of places to stop in for a sip. Try award-winning small-batch wine at Cameron’s Winery in Northfield, partake in seasonal tastings at West County Cider in Shelburne, and sample offerings at The Brewery at Four Star Farms in Northfield and Tree House Brewing Company in Deerfield. Foodies can’t miss a stop into swanky speakeasy Le Peacock for small plates and craft cocktails, and Yankee Candle Village is a must-see for fragrance fans. From ziplining to rafting, adventure is always within reach with the Deerfield River and Valley at your fingertips. Fun year-round and seasonal events also give visitors a chance to meet locals and explore beautiful landscapes. Mainstays like the summertime Green River Festival, autumn’s Franklin County Fair and the Great River Challenge Off-Road Triathlon draw enthusiastic crowds. Be sure to check the calendar for farmers markets, monthly art walks in downtown Greenfield and live music at the Guiding Star Grange.

You’ll find plenty of convenient options to get to Western Massachusetts. Fly into Bradley International Airport (BDL) in Hartford, Connecticut, then rent a car for the half-hour drive to the area. If you’re arriving at Boston Logan International Airport (BOS), you’ll drive about two hours to reach Western Massachusetts. From New York City, Amtrak offers train service to Springfield, Northampton and Greenfield aboard the Vermonter.