In ten years of running this Boston-based travel blog, my articles about vacations and day trips in the Berkshires, MA Mountains have proven mighty popular. Now that so many of us are yearning for fresh air and nature, it seems the perfect time to compile these together into 14 travel ideas of what to do in the Berkshires.
Browse this list of my favorite Berkshires, MA attractions for ideas on what to do and see, ranging from “Of course!” picks like the tallest mountain in Massachusetts (Mount Greylock), to the tallest waterfall (Bash Bish Falls!), to surprising hidden gems like a certain tiny planes airport, or fluffy, fabulous alpacas.
What to Do in the Berkshires, MA
Western Massachusetts offers delights for all ages! Many of these ideas for what to do in the Berkshires are outside in nature and provide lots of fresh air... and most are FREE! See what's on offer...
From the highest mountain in Massachusetts, let's move to the tallest single drop waterfall: Bash Bish! Just make sure to follow my advice in this linked article if you go, because there are two different entrances with very different hiking experiences in the state park -- and I don't want you to make the same mistake we did!
Watching vibrantly colored small planes take off is one of our family's favorite pastimes in the Berkshires. Walter J. Koladza Airport is a friendly, fascinating spot that is well worth an afternoon stop.
This sprawling building redefines what a museum can be, showing modern art of all sizes and forms. You could spend a full day here -- or more -- and satisfy kids and adults alike. Don't miss the musical instrument room!
This famed historic hotel is the definition of unique. Every inch of the building is packed with character and curios. Learn the full story and see pictures here -- and consider stopping by for outdoor patio dining.
One of the most famous museums in Western Massachusetts is The Clark: a collection of art which soothes the soul and makes the imagination soar. I wrote this article about how visiting it with my brother helped bring us closer together -- and it might do the same for you and your loved ones.
Learn about Cheshire Cobbles: a relaxed hike with an outlook near Cheshire, MA. This article also describes the Bed and Breakfast nearby which we loved, and though it's now under new management, it still gets great reviews.
Though the focus of this article is Western Massachusetts, if you're driving from Boston you'll pass through Hampshire County after two hours, and I can't resist recommending a peek around the charming town of Northampton.
From the Eric Carle Museum of Picture Book Art, to a free and fabulous indoor playground and farm (Mill 180 Park), to epic apple cider donuts, consider at least one of these attractions in Hampshire County an hour from the Berkshires.
Some of the best Barbecue I've ever eaten is found in Sturbridge, en route to Western Massachusetts. See where to find it here, along with a fascinating optical museum and great coffee in nearby Southbridge.
For those driving from Boston to the Berkshires, remember that just an hour outside the city sits famed Old Sturbridge Village: the absolutely charming 18th century town and farm which is an interactive outdoor museum to delight all ages. I was stunned by how moving and beautiful I found it!
Berkshires, MA Hotels and Rentals
Ok, so these articles have convinced you to visit the Berkshires… so where to stay? Here are some suggestions (in the form of affiliate links which you may choose to use to provide a commission at no extra cost to you) of Berkshires, MA hotels and rentals. The first option is to browse these ratings of hotels to see if any fit your location, cost, and style desires.
While I’ve enjoyed many a hotel and inn in Western Massachusetts, my current favorite option now that I have young kids is to rent a whole house (click here to see the company I use) so that extended family can all stay together. It often ends up being much more affordable and convenient than a hotel, though each has its perks.
What Do YOU Like to Do in The Berkshires, MA?
These ideas only scratch the surface of the MANY wonderful things to do and see in Western Massachusetts, and the MANY answers to the query: “What to do in the Berkshires???” I didn’t even touch yet on Tanglewood, the Norman Rockwell Museum, charming small towns, hidden lakes, and goat yoga — but it’s a start! What are your votes for attractions in this area? Do share!
The author, Lillie Marshall, is 6-foot-tall National Board Certified Teacher of English, fitness fan, and mother of two who has been a public school educator since 2003. She launched Around the World “L” Travel and Life Blog in 2009, and over 4.2 million readers have now visited this site. Lillie also runs TeachingTraveling.com and DrawingsOf.com. Subscribe to her monthly newsletter, and follow @WorldLillie on social media!