The Perfect Summer Getaway

For decades, the Berkshires has served as the de facto summer retreat for the Boston and New York City elite, offering world class wining and dining, lavish hotels and wellness resorts, and countless opportunities to escape into the breathtaking Appalachian nature. But in recent years, the region has undergone a transformation of sorts, surging in popularity and becoming a much more accessible destination with something to be enjoyed by everyone.

Summer is the most popular time of year to visit, with good reason, and being just a few hours away from both New York City and Boston, the Berkshires is the perfect place to escape from the city and take a last minute summer vacation.

Whether you can only come for a long weekend, or visit for a full week or more, there’s an abundance of things to see, taste, experience, and do in the region, so let’s break down some of them and start you off on planning your perfect Berkshires getaway!

Now, it wouldn’t be possible to talk about the Berkshires without diving into the spectacular nature of the region. Being in the heart of the Appalachian mountains, there’s no shortage of incredible peaks, parks, forests, and nature reserves. No matter where you turn, you’ll be greeted with lush rolling hills and beautiful expanses of pristine nature. Once you experience it yourself, you’ll understand why the region has been a major source of inspiration for countless artists over the decades!

And of course, with this nature comes an abundance of hiking trails of all difficulty levels, and we’ve even compiled a list for you of some of our favorites. If you’re up for a challenge, take the trek up to the summit of Mt Greylock on a clear day, the highest point in Massachusetts with sweeping views of the entire region. For a more mellow journey, you’ll find plenty of gentle walks through pristine meadows and forests in the southern section of the region, including an easy hike to the stunning Bash Bish Falls.

After hitting the trails, chances are you’ll be in need of a recovery day, and there’s no better way to rest your legs than to treat yourself to a spa day at one of the many wellness resorts in the region. In Lenox alone, you’ll find Canyon Ranch, Miraval, and Blantyre, each with their own luxurious world-class spa facilities. Staying at these resorts is typically expensive, but fortunately, day passes to their spas are usually available in limited quantities. Just be sure to book as far in advance as possible to secure your visit!

Alternatively, if you’re not really the spa type, you’ll find tons of great shopping all throughout the region. Nearly every town in the Berkshires has their own shopping district, but Great Barrington and Pittsfield arguably have the best. Both cities are home to a large and lively downtown area with a variety of boutiques, restaurants, cafes, and more. You could easily spend an entire day in each city just walking and shopping around to your heart’s content!

The Berkshires is also home to a growing wine and craft beer scene thanks to the influx of younger adults and millenial visitors in recent years, with six breweries and a handful of wineries in the county. Barrington Brewery in Great Barrington is renowned for its delicious barn brewed beers, while Big Elm brewing in Sheffield has quickly become one of the most popular amongst  visitors and locals alike.

But if you’re more of a wine enthusiast, Balderdash Cellars in Richmond is a must-visit. The quirky boutique winery blends and presses premium California grapes to create some highly-acclaimed Berkshire-made wine that you’ll be hard pressed to find anywhere else. Have a glass (or two) and sit out on the sweeping lawn while watching the sunset over the mountains for a perfect summer evening out.

And lastly, we can’t skip over the bounty of cultural attractions that call the Berkshires home. From art museums to sculpture gardens, historical house museums to gilded age mansions, you could spend weeks in the region and still not check off all of the cultural offerings. Lenox is particularly rich in such attractions, with The Mount, Ventfort Hall, and Tanglewood all within the city limits.

Now for the most important question, with so much to experience across the Berkshires, where should you stay?? After all, the region is quite large, and you don’t want to be spending too much time in the car everyday driving from one town to the next!

Well, for the best experience, we’d highly recommend staying in one of our luxury apartments in the heart of downtown Lenox. Not only will you be mere steps away from the vibrant and lively downtown scene, full of great shopping, restaurants, bars, and attractions, but you’ll be just a short drive away from everything else in the region thanks to Lenox’s central location!

From hiking and exploring to shopping and pampering, sipping and relaxing to wining and dining, the Berkshires has everything you could ask for in a summer getaway! All that’s left to do now is book your stay, pack your bags, and hit the road! 

Don’t wait too long to book though, the summer is going to be over before you know it!