Exploring the Towns of the Berkshires

The towns in the berkshires have a unique charm, each containing attractions and activities for all ages. With plenty of shopping opportunities, excellent live performances, and more, the Berkshires have so much to offer that one could easily spend days just exploring the various towns.


In this article, we’ll go over 3 of the biggest towns in the county and cover some of the best attractions there.

A row of brick buildings on a city street

downtown pittsfield, ma

Being the most populous town in the area, Pittsfield has plenty to offer for people of all ages. For example, Downtown Pittsfield, MA has some of the best opportunities for shopping in the Berkshires. The biggest shopping opportunity here is the Pittsfield Farmers Market, a teen-run event that features local goods and crafts alongside live music, chef demos, children’s activities, and more. 


Visitors to Downtown Pittsfield, MA will also find a number of local stores that sell quality goods such as:

  • Art Supplies
  • Boutique Clothing
  • Tabletop Gaming
  • Home Decor
  • Novelities
  • And so much more!


Downtown Pittsfield, MA also regularly holds events like the 3rd Thursdays Street Festival and is home to the Barrington Stage Company, the Berkshire Theatre Group’s Colonial Theater, and a host of art galleries.


DOWNTOWN NORTH ADAMS

Despite being known as the smallest city in the Commonwealth, North Adams is brimming with culture. The town aesthetic is a blend of both the old and the new, with many of the buildings being built in the 19th century, showcasing modern art and wares.


Downtown North Adams, also known as the Cultural District. has a multi-seasonal draw, with almost a dozen annual events including WinterFest and the Fall Foliage Festival and Parade. The biggest attraction in the area is Mass MoCA, a haven for the arts that brings hundreds of thousands of visitors to the town every year.


Walking down the streets of the Cultural District will allow you an up close and personal view of some of the best emerging artists in the area. On top of the dozens of creative entrepreneurs running stores in the area, the summer-long DownStreet Art initiative is truly a sight to behold as you’ll find public art displays, performances, unique vendors, and plenty of family fun activities.


Downtown North Adams is a wonderful destination for those who love to admire art in any form.


A city street with a lot of cars parked on the side of it.
A village in the middle of a vineyard with a church in the background.

GREAT BARRINGTON

What once was a well-kept secret of the Berkshires is now growing ever more popular as a tourist destination. Great Barrington has a rich history having one of the oldest streets in the U.S. still in use (Railroad St.), Home to the first American street outfitted with stop lights (Main St.), and is the birthplace of the famed civil rights activist W.E.B Dubois.


However, there is much more to this small town than historical value. Great Barrington is surrounded by gorgeous natural beauty and offers hundreds of trails allowing you to explore the region.


Walking down Main St. will allow you to discover plenty of local vendors and eateries that serve up wonderful local products and dishes alongside genuine, small-town charm. You’ll also find the Mahaiwe Performing Arts Center, a historical venue that has been continually hosting events, performances, and programs for over 110 years.


A foggy forest with mountains in the background

GET YOUR DESERVED GETAWAY AT BONNIE BRAE

Located on the outskirts of Pittsfield, Bonnie Brae is the perfect place to go to destress from your day-to-day life. With affordable cabins and campground facilities, you can always have a tranquil place to rest after an exciting day exploring the Berkshires.


Browse our listings and book today!