things to do Near Pittsfield, MA

Take a look at our guide to area activities!

You'll find plenty of exciting opportunities when visiting the small towns in the area.

We have a number of museums and galleries that are brimming with art and culture.

After having a grand time recuperating while on vacation, it’s understandable that you’d want to take something home to remember your trip. Here in western Massachusetts, there are plenty of opportunities for shopping in the Berkshires around, especially when it comes to Berkshire antiques.

Visiting a local brewery or winery and tasting a local libation paired with a savory meal can be a great way to spend the day. Lucky for you, the Berkshires have many fantastic creators of adult beverages, enough that it’s a difficult decision to determine which ones to stop by during your visit. 

We’ve put together a list below of some nearby locations. Keep in mind that this is by no means a comprehensive list of wineries and breweries near Pittsfield, MA, just some recommendations to get you started.

There is a long tradition of live music here in the Berkshires. Here are some of our recommendations for music festivals that you should try!

Explore the joy of outdoor water activities in the Berkshires' nearby lakes, ideal for fishing, boating, and swimming.

The Berkshires have some of the best hiking in Massachusetts. We’ve put together a list of hiking and biking trails to show you what’s available.