The Berkshires

Around 2.5 hours north of NYC, lies the Berkshires; a rural region of Massachusetts that is characterized by its highland geographic features. For those looking for a day trip or a quick weekend away while getting both culture and adventure, then this is an area for you. Geographically, the Berkshire Mountains are a part of the greater Appalachian Mountains affording visitors with great hiking and other adventures. The region is renowned for its recreational opportunities as well as a vibrant music and arts scene. This makes the Berkshires a favorite getaway for residents of major east coast cities such as New York.

Though many people think of the Berkshires as a trip destination that is perfect for a summer getaway or for a fall trip focused on seeing the region’s stunning foliage. The truth is that the Berkshires are a travel destination that offers plenty to do regardless of the time of year that you go there. In winter you’ll have countless opportunities for outdoor activities such as skiing, snowboarding, snow tubing, and hiking.

The Berkshires are the perfect getaway from the hustle and bustle of New York City and other east coast urban centers. Whether you head there for a short weekend trip or an extended stay, it is a region that never ceases to offer up pleasant surprises. Let Voyavoy help you plan a trip to the Berkshires that will leave you with memories that will stay with you for a lifetime.

The Top Areas and Towns to Visit in the Berkshires

The Berkshires are known for their stunning beauty and majestic hills. They are also known for their unique communities that are scattered throughout those hills. Listed below are a number of unique towns in the Berkshires that are a must for those who want to know what to do when they take a trip to the region.

Lenox

The Berkshires community of Lenox is the heart of culture for the Berkshires region. It is famed for the Tanglewood Music Festival that occurs there each year. This festival features the Boston Symphony Orchestra and consists of a series of concerts featuring a range of music such as symphonic music, musical theater, contemporary music, jazz, and pop. If classic drama is more your thing then be sure to check out the Shakespeare & Company show. Each fall they organize a program called The Fall Festival of Shakespeare, which is a must-see if visiting during that time.

In addition, you’ll find unique estates and bed and breakfasts that are quintessential New England. Rolling hills and green grassy knolls are common. Walking through the town you’ll find plenty of shopping, galleries, and stores catering to handicrafts.

Pittsfield

The town of Pittsfield is famed as a cultural center within the Berkshires. Among the highlights of this charming community is the Herman Melville House. Visitors to the house get a unique insight into the life of the famed Moby-Dick author and will get the opportunity to explore the restored sections that show the building in its original state when Melville was an author in residence

If you enjoy biking, the Ashuwillticook Rail Trail is paved and perfect for a scenic ride by Cheshire Reservoir and the Hoosic River. The total distance is 12.7 miles and runs through multiple towns, such as Cheshire, Lanesborough, and Adams. During the winter it is open for cross-country skiing.

Jiminy Peak Mountain Resort in nearby Hancock offers activities for everyone and around the year. During the winter season, there are 45 skiing trails to choose from. During the summer season, you can experience scenic chair lift rides, a mountain coaster, an aerial adventure park, mountain biking, and many other things.

Great Barrington

There is a good reason why Great Barrington holds the distinction of once being named America’s Best Small Town by the Smithsonian. For those music fans who know all of the classics, this town is the inspiration for Arlo Guthrie’s song "Alice’s Restaurant”, This charming community is home to more than 70 restaurants as well as a wealth of truly unique shopping possibilities. Taking a walk through this Berkshires community is a must for a weekend trip or an extended one.

There Is Something for Everyone in the Berkshires

The good news for those who want to know what to do in the Berkshires is the fact that there is something for everyone. Let us tell you about some of our top picks for activities for families, couples, and solo travelers.

Great Experiences for Families

There is no shortage of great activities for families who are taking a trip to the Berkshires. Among the top spots for a family day out in the region are the Magic Wings Butterfly Conservatory and Gardens. The facility is open on a year-round basis and features more than three thousand stunning butterflies. There is also a gift shop where you can purchase souvenirs to help you remember your time at the conservatory.

Hancock Shaker Village is a living history village for experiencing how Shakers lived. The Hancock Shaker Village is also a working farm growing vegetables and herbs, as well as livestock. Kids will love the hands-on activities at the discovery barn and seeing all the farm animals with their babies.

The Berkshires Offers Plenty of Romantic Opportunities for Couples

There are plenty of opportunities for a romantic trip when you head to the Berkshires. Taking in the sights of natural beauty along the Mohawk State Trail is a great way to combine quality time with a loved one and outdoor activity.

If you prefer something a bit calmer, you should definitely head to The Mount, author Edith Wharton’s Home. This gorgeous estate is a national historic landmark and cultural center. Another place worth visiting is the Berkshire Botanical Garden, a beautiful place to enjoy the wonders of nature and for a romantic walk. Afterward, head to Great Barrington to enjoy dinner at one of the town’s 70-plus restaurants.

Solo Travelers Have a Great Time in the Berkshires Too

If you are someone who lives for the experience of solo travel, the Berkshires do not disappoint. If you are in need of some luxurious wellness experience, Canyon Ranch is the perfect place to enjoy some time enjoying personal contemplation while you take in the stunning scenery. This can be followed up by a trip enjoying the sights and sounds of the famed Tanglewood Music Festival that is held every year from July to August. Tanglewood is the summer home of the Boston Symphony Orchestra and a beautiful setting for concerts. In addition to symphony concerts, you can enjoy choral music, chamber music, musical theater, jazz, and pop music.

Final Thought on Traveling to the Berkshires

The stunning natural beauty and the vibrant, historic culture of the Berkshires continues to attract visitors to the region on a year-round basis. It is easy to see why the region is such a hotspot for travelers given the sheer number of things to do while visiting the region.