WEEKEND GETAWAY: Berkshire County, Massachusetts

Berkshire County, or The Berkshires, is a region in Western Massachusetts. It is known for beautiful mountains, a vibrant arts scene, and plenty of outdoor activities to keep you busy all year round. I spent a week in Western Massachusetts visiting a friend and got to see a lot of this area and had a great time! This part of New England may not be at the top of your list, but it is definitely worth checking out, especially in the summer.

You have a few options for getting to Berkshire County. You can fly into Hartford/Bradley, Boston, Albany, or NYC. You will need to rent a car for your trip, but the drive is so beautiful! Especially when you are not used to seeing mountains. You can also take the Amtrak. Once you are here, there is no shortage of festivals, events, shopping, theater, music, and outdoor fun.

There is a great arts and culture scene in the Berkshires. This is, after all, where Norman Rockwell worked in his studio in Stockbridge and where Herman Melville was inspired to write Moby Dick. The Norman Rockwell Museum is definitely worth a visit. The grounds themselves are beautiful and contain a lot of history. The museum also has Norman Rockwell’s studio and all of his Saturday Evening Post covers. You can visit Herman Melville’s home in Pittsfield, Arrowhead, and learn more about his life.

This area is also well known for its regional theater. I was able to see three great plays while I was there: Million Dollar Quartet, Children of a Lesser God by the Berkshire Theatre Group and Ragtime by the Barrington Stage Company. Throughout the summer there are so many options to see great plays with talented performers. Many of the performers are from Broadway or Off Broadway shows who go to the Berkshires during the off season.

If you are looking for some outdoor adventures, there is great hiking and biking trails. In fact, the Appalachian Trail goes through the Berkshires for the serious hikers. You can hike to the top of Mount Greylock, which is the highest point in Massachusetts at 3,489 feet, and where you can see five states: Massachusetts, Connecticut, New York, Vermont, and New Hampshire. (Or you can drive to the top and just enjoy the views.)

When you are in Berkshire County, you are within driving distance of a lot of great areas. You are about 2 hours from Boston, 3 hours from New York City, an hour and a half from Six Flags New England, and about an hour and a half from Albany. If you are road tripping through New England, you should definitely make sure to see the Berkshires!

Summer is when there is the most going on in Berkshire County, but it is a year round destination. You can be a “leaf peeper” in the fall to see the gorgeous color changing leaves, or visit in the winter for some great skiing.

Other things to do in Berkshire County:


Hancock Shaker Village

Shakespeare & Co. Theater

Jacob’s Pillow Dance Festival


Alpine slide

Museums, historic sites, and gardens

Have you visited The Berkshires? What are some of your favorite things to do there? Let us know in the comments!

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