Best Things to do in the Berkshires of Massachusetts

things to do in the berkshires
A view of Laura's Tower during a summer hike

The Berkshires are a Special Place

My family has a lake home in the Berkshires. The Berkshires is a region located in western Massachusetts. After spending a few days in the Berkshires, you’ll quickly understand why it is such a special place. There is so much to eat, drink, see and do. And the people are very kind. I feel very fortunate to have a family home in the Berkshires.

Hike the Berkshires


Hiking is a Must

There are tons of hikes all of varying difficulty and length. So whatever you’re looking for, you can find it. My favorites include Laura’s Tower. It’s heavily wooded and quiet. It doesn’t take too long to get to the top and once you do, there is a staircase and platform that allows you to get a little higher and get an even better view of the surrounding towns.

We also frequent Monument Mountain, which is very steep. It’s an intense workout on your way up, but once you get to the top, the vistas are incredible, and the walk back down is quick!

Lastly, Olivia’s Overlook is exactly that, an overlook where you can see the Stockbridge Bowl and surrounding mountains. Click here for an extensive list of some of the best hikes in Massachusetts.

Drinks and live music in the Berkshires

                                   With my family at the Lion’s Den for drinks and live music.

You’ll Never Run Out of Great Food Choices

First Pick a Town

There are so many restaurants in the Berkshires and the surrounding towns. Some of our favorite options are in Stockbridge, Lenox, Great Barrington, and Lee.

Then Pick the Type of Cuisine You’re Craving

Bistro Zinc is upscale with high-quality cuisine. The Red Lion Inn is relaxed and has a great outdoor seating area. There is also a bar in the basement called the Lion’s Den, which is fun for late nights and they often have live music.

Prime Italian Steakhouse and Bar is a fancy Italian restaurant we usually go-to for a birthday or holiday. The portions are large and it has a nice upscale ambiance. If you’re looking for a relaxed place to grab breakfast, lunch, or just a coffee, head over to Haven. They offer free coffee refills so people often stay a while reading or working on their laptops.

People in the Berkshires Love Being Outside

Take a Swim in the Stockbridge Bowl

There is so much to do in the Berkshires. The Stockbridge Bowl lake is definitely a spot to check out. It is a fairly quiet lake, so you won’t find people zipping around on speed boats too often. You’ll likely see small sailboats, a lot of kayaks, and fishing boats. There is a small public access beach on the south side, which I recommend checking out in the summer because the water quality is really nice and clear.

Stockbridge Bowl dock


                                    A view of Stockbridge Bowl as the morning fog rolls away.

Practice Yoga at Kripalu

On the north side of the lake, you’ll find the Kripalu Center for Yoga and Health. They offer a variety of packages, from a one-time massage to an entire week of meals, yoga classes, educational seminars, and paddle boarding lessons on the lake. You can’t help but feel relaxed when you’re at Kripalu.

Tanglewood performance in Stockbridge Berkshires
Tanglewood concert with my family

Listen to Music and Comedians at Tanglewood

Down the road from Kripalu is Tanglewood where you’ll find the Boston Symphony Orchestra Playing. You can also catch great shows, like Steve Martin and Martin Short: A Show You Will Forget for the Rest of Your Life. Once gates open up, people fill in opening up lawn chairs and setting up their picnics. Be sure to get there early if you want a good spot!

Say Hello to Edith Wharton and Norman Rockwell

We’ve also been to The Mount, which is Edith Wharton’s home and a National History Landmark. They offer tours of the home and live concerts on the back wrap around deck, which overlooks expansive manicured gardens. If you love museums, you’ll never be bored. My favorite is the Norman Rockwell Museum.

Sailing the Stockbridge Bowl


My dad and I sailing on the Stockbridge Bowl in a boat he made!

A Trip You Won’t Forget

The Berkshires are a special place and every time I go I stumble upon another gem! I’m so fortunate that my parents have a lake house in Berkshires and after ten years, I still want more. There is always a new hike to explore, another restaurant to check out and so much culture to experience. Looking for more inspiration? Check out my post on hiking Winona, Minnesota to see the fall colors.

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