Berkshires, MA, Guide and Information

In Western Massachusetts, the Berkshires await as an outdoor playground and a luxury getaway for those hoping to relax just a short trip from some of the East Coast’s busier urban hubs. Here, you’ll find lots to see and do, from ski areas to museums, theaters to galleries, but also wonderful inns and boutique hotels to act as your base camp during your explorations of the region, as well as amazing restaurants to keep you fed.

For the best local bites during your Berkshires stay, you’ll want to be sure to add some of these top spots to eat in the Berkshires to your itinerary.

The Berkshires of Massachusetts is a vacation playground within easy reach of Boston, filled with fun for every season. You can hike in the summer, ski in the winter, enjoy arts, culture and history no matter the weather — all the while also reveling in the high level of luxury that this destination offers its most discerning visitors.

That said, when it comes to finding a unique, top-rated place to stay in the Berkshires, you won’t be left wanting for options. Here are some of the best spots that you’ll want to book now.

New Yorkers have the Catskills. Philadelphians have the Poconos. Bostonians have the Berkshires. But while this western Massachusetts mountain escape destination is a favorite for families, luxury retreat-seekers and outdoor adventurers in Beantown, the Berkshires also attracts its fair share of travelers from other parts of the country. If you’re among them, here’s everything you need to do during your very first visit.

The Berkshires is truly a four-season destination, with something to do no matter if you visit in spring, summer, fall or winter. During the colder months, you’ll find skiing aplenty, plus other winter sports, if you prefer something a little more low-key. During the summer, hiking and biking opportunities are abundant. Want something really high-energy? Try some white-water rafting. Prefer something more relaxing and chill? Get in a round of golf or head out in a kayak.

How do you begin to encapsulate a jumble of charming towns, one city and a host of iconic sites located within one large geographic area? Let’s try. First of all, know that The Berkshires refers to the part of western Massachusetts situated at the tail end of Vermont’s Green Mountains. So The Berkshires refers to both a region and the mountains. (They’re actually more like rolling blue-green hills with Mount Greylock, the highest point in Massachusetts at just under four thousand feet, as its pinnacle.)

Whenever there’s a place where the well-to-do have vacationed for years, you can bet there’s a vibrant cultural scene. In The Berkshires, it explodes.

Whether it be the visual or performing arts, there’s enough to keep you going here for weeks. And that’s not just the case in the summer, since many of the arts centers remain open year-round.