From visiting the picturesque Berkshires to a pitstop for Indian food Jerry Seinfeld style, Western Massachusetts offers an abundance of splendid offerings. It’s a lovely place for those who appreciate the outdoors. There are dozens of storybook towns in the Berkshires and beyond, such as Lenox, Stockbridge, and Deerfield.
Before we jump into our favorite things to do in Western Massachusetts, let’s clear the air on a common misconception!
What is Western Massachusetts?
Many, even Bostonians, believe Western Massachusetts to be synonymous with the Berkshires. However, the Berkshires is only a part of Western Massachusetts. This Western part of the state includes many other towns outside of the Berkshires such as Springfield and Amherst.
The map of Western Massachusetts below shows the dozens of other towns in the region in addition to the seven Berkshires towns, which we highlight later. The farther west you get from Boston, the more rural the area becomes, and then eventually you’ll find yourself in upstate New York!
What are the Berkshires?
The Berkshires are a group of seven towns in Western Massachusetts-Stockbridge, Lenox, Lee, Pittsfield, North Adams, Great Barrington, and Williamstown. The towns reside in some of the world’s oldest mountains, dating back over 500 million years! These old, but mighty, mountains are great for fall foliage, skiing, and hiking!
Best things to do in Western Massachusetts
Western Massachusetts begins with a town called Ware, Massachusetts which is about 90 minutes from Boston. Then it extends all the way to Mount Washington, Williamstown, and Stockbridge to name a few. Each region of Western Massachusetts offers something unique to explore. Below are a few of our favorite thing to do in this part of the state!
This darling inn is over 250 years old! You can ride The Red Lion Inn’s antique gold elevator, stay in their charming rooms, have a delicious farm-to-table meal and take a dip in their 365-day outdoor heated pool!
Another amazing stay in Western Mass is the wellness resort Miraval Berkshires. Whether a guest or just visiting the spa, you’ll be able to get a full mind, body, and soul reset at this wellness oasis.
3. Take a horse-drawn carriage through historic Deerfield
Grab lunch at Champney’s (don’t skip the Ceasar salad at this cozy spot in Deerfield) and after you’ll be escorted by horse-drawn carriage from the restaurant’s doorstep! Deerfield is also home to Magic Wings, an interactive Butterfly Museum!
The Yankee Candle Village in Sturbridge offers something magical for all ages! At Wax World, guests can create their own layered candle for dozens of colors and scents in one!
5. Grab a bite at Granny’s
This Springfield bakery offers something to savor. Don’t skip Granny’s handcrafted Egg and Cheese biscuit. It’s the food equivalent of a fuzzy blanket.
6. Tour the historic Naumkeag
The Berkshires are home to 70 Gilded Age mansions. Some have transformed into hotels and others are preserved as museums or touring venues. Naumkeag is a gorgeous place year-round and offers unique lights experiences open to the public, with an entry fee.
Enjoy dazzling pumpkins in the fall or flowers for spring. And of course, it’s home to one of the state’s best winter lightshows!
7. Visit the Norman Rockwell Museum
The famed illustrator lived in the quaint Berkshires town of Stockbridge, where he drew plenty of inspiration. The museum houses all 323 of his covers for The Saturday Morning Post.
8. Get outdoors in the Berkshires
Western Mass is a playground for those who love the outdoors, especially in the mountainous Berkshires. There are hundreds of idyllic spots for every kind of activity whether it be waterfall hiking or skiing!
A fun fact about Western Massachusetts is the Holyoke St. Patrick’s Day Parade and Road Race is so hilly, it is the shortest qualifier for the Boston Marathon! Generally, marathoners have to run another marathon or raise money for charity to qualify to run Boston. But this 10K (only 6 mile) race is so challenging it counts as a Boston Marathon qualifier!
9. Catch a comedy show in Springfield
Springfield offers up a unique city life different from Boston. You can visit the Museum of Basketball and catch a comedy show at Mass Mutual all in the city.
10. Ride the longest zipline in America
The “Catamonster,” located at Catamount Mountain Resort is so long it travels from Massachusetts to New York! The zipline is raised 250-feet above ground and will send riders at speeds up to 55 miles-per-hour!