When most people think of Massachusetts, they think of two things: Boston and the beaches of Cape Cod or the North Shore. Oh, and the Red Sox, of course. Even among native Massholes, there’s a tendency to think that everything west of Boston is a wooded wilderness with little to entice a traveler. While Western Massachusetts is indeed full of green woodlands and is famous for its scenic Berkshire Mountains, there’s more to do there than visit the Basketball Hall of Fame.

The Pioneer Valley, about two hours west of Boston, is home to the Five Colleges — Smith College, Amherst College, Hampshire College, Mount Holyoke, and the University of Massachusetts. The vibrant social, cultural, and adventure scene that has grown around these schools makes the area one of the most lively in the whole state, and well worth visiting for a weekend break from Boston.

Editor’s note: Travel is still widely restricted. Some places may be closed, and events may be canceled or postponed. Check the local health guidelines and plan now to travel when it’s safe to do so.

The Five Colleges

Mount Holyoke in Western Massachusetts

Photo: Feng Cheng/Shutterstock

As you can imagine, a community with five colleges all within a few miles of each other is a community where there’s always something to do. Amherst is the epicenter of the Pioneer Valley, home to Amherst College, the University of Massachusetts, and Hampshire College. Nearby Northampton, a nearby town with a vibrant arts and music scene, is the site of the all-female Smith College while another women’s college, Mount Holyoke, is located in nearby South Hadley.

The cultural activities, social gatherings, educational lectures, and sporting events sponsored by these colleges aren’t just for the students — they’re often open for visitors to enjoy as well. The close proximity of these five schools means there’s always a live sport to attend, university museums to visit, student theater to watch, and cheap beers to consume.

When you think of a college town, you likely think of an abundance of bars and music venues. You can find that here, but the Pioneer Valley is more than just a college community. Its entertainment offerings extend far beyond the campus life and a college crowd. From open mic nights to karaoke, there are more venues in rural Western MA than you might think, and they draw world-class acts including the likes of Bob Dylan and Miranda Lambert.

The Academy of Music Theatre in Northampton is one of the area’s most iconic music venues. Dating back to 1890, the theater hosted acts like Harry Houdini, Mae West, and Sarah Bernhardt, and for over a century it has been a popular venue for concerts, lectures, opera, and theater.

Those seeking live music in a more casual environment — i.e., where you can drink — should check out The Harp Irish Pub in Amherst, which is known for its relaxing atmosphere and traditional live Irish music. For a somewhat rowdier experience, head to Stackers, McMurphy’s, or Monkey Bar in Amherst. As long as you don’t mind the college crowd, there’s nowhere better to throw back $2 PBRs.

It’s Western MA’s historical and cultural center

Old Deerfield Village Historic District in Western Massachusetts

Photo: Jeffrey M. Frank/Shutterstock

As you might expect from an area steeped in academia, in a state full of history, the Pioneer Valley is a cultural oasis. Settlements in this part of Western MA date back to the 1600s, and several institutions exist to preserve that heritage. From museums and monuments to old farms, taverns, and libraries, this college community’s cultural offerings are perhaps even more enticing than cheap college beer.

Historic Deerfield, under a half-hour north from the center of Amherst, is the best way to really experience the area’s history. Consisting of 11 house museums, these historic properties allow visitors to explore hundreds of years of history along an original 330-year-old street. The experience also includes access to outdoor activities like walking tours, the Cook’s Garden — which provides fresh ingredients for the museum’s open-hearth cooking demonstrations — and the Old Burying Ground where many of the original settlers are buried. It’s not quite Colonial Williamsburg, but it’s one of the best sites for history buffs in all Massachusetts.

Bookworms will want to check out the Emily Dickinson Museum and homestead in Amherst. Few things are more satisfying than actually visiting the home of one of your favorite writers. In this house, Dickinson wrote some of her most famous poems in the mid-1800s, often drawing inspiration from the gardens on the property.

Historic houses are ubiquitous in rural New England towns, but don’t let the plethora of museums and historic farms distract from the area’s more unique offerings. Amherst College is home to the Beneski Museum of Natural History, displaying artifacts from Africa, Asia, and South America, as well as dinosaur fossils and rare geological specimens. There’s also a Yiddish Book Center in Amherst dedicated to telling Jewish history through Jewish books and educational programs.

College towns are typically synonymous with a robust art scene, and the Pioneer Valley is no different. Whether it’s the Hampshire College Art Gallery, which serves as an exhibition space for visual arts, Amherst College’s Mead Art Museum, or the Eric Carle Museum of Picture Book Art, the art scene in the Amherst area could hold its own even with that of Boston.

Festivals and events

Three County Fair in Western Massachusetts

Photo: Three County Fair/Facebook

The state’s biggest festivals aren’t just reserved for the Boston area. Particularly in the summer, the Pioneer Valley is home to festivals that alone make the trip worth it.

In May, you can look forward to the Paradise City Arts Festival to really kick off the summer. Paradise City produces an award-winning show of contemporary craft and fine art in Northampton, showcasing the work of some of the country’s most prominent craftsmen, including sculpture, ceramics, jewelry, painting, and art glass. If performance art is more your style, the Ko Festival of Performance takes place every summer at Amherst College. The festival is five weeks of original theater works created by artists according to a predetermined theme.

Also in June, Django in June celebrates the study and performance of Gypsy Jazz at Smith College with famed guitarist Django Reinhardt. The festival’s main event is the Django Camp, where musicians can immerse themselves in the jazz style under the instruction of international artists. The event caps off with a weekend of concerts at the Academy of Music and other smaller venues around town.

Arguably the most notable event in the area happens in September. The Three County Fair in Northampton is the oldest continuously operating agricultural fair in the country. In early September each year, over 50 acres of fairgrounds play host to livestock and agricultural contests, top musical entertainment, a fair museum, food vendors, demolition derbies, and a midway with rides and games.

This summer, many regularly scheduled festivals may be affected by the COVID-19 pandemic, so make sure to check the festival’s most updated information before planning your trip.

Outdoor adventure

Zoar Outdoor in Western Massachusetts

Photo: Zoar Outdoor/Facebook

Ok, it’s finally time to lean into the Western Massachusetts stereotype of trees, trails, and miles of unspoiled nature. The area has an abundance of kayaking, hiking, skiing, and cycling to help you work off that post-Monkey Bar hangover. Miles of railroads have been converted into bike paths, making for a network of bike trails perfect for exploring the rural landscape.

Skinner State Park in Hadley has plenty of hiking trails with views of the Connecticut River Valley, as well as a self-guided geology walking tour. The nearby Holyoke Range, which actually extends from the Long Island Sound to the border of Vermont, is known for its Horse Caves and ledges found along the New England Scenic Trail that once served as the hiding place for the fighters of Shays’ Rebellion in 1897. If you’re looking to stay a bit closer to town, the Manhan Rail Trail connecting Northampton to Easthampton is a great way to experience the area’s towns by bike while also getting a dose of nature.

Even if you don’t have a boat, you can still rent one at the Oxbow Marina in Northampton and spend the day on the Connecticut River. You can also go tubing or just hang out and enjoy the view. If you’re visiting during June or July, make sure to catch the epic water ski shows every Friday night.

Those looking for some real adventure probably won’t mind driving just over a half-hour to Charlemont where you can go zip lining with Zoar Outdoor. Spend the day soaring through the Berkshire trees, enjoying views of the Deerfield River Valley and the northern Berkshires. Zoar lets you ride 11 different zip lines as part of the experience. If that’s not quite high enough above the ground for you, head 40 minutes west to Worthington and take a hot air balloon flight. Worthington Ballooning will bring you high above the fields, rivers, forests, and mountains of Western Massachusetts, giving you a dramatic perspective of the area’s natural beauty.

Anyone who’s been to the Pioneer Valley knows the area isn’t “just a college town,” and Western MA isn’t “just a bunch of farms.” It strikes the perfect balance between classic New England culture and history, outdoor adventure, and good old-fashioned nightlife. It’s a combo that hits as good as the Red Sox on their best day.