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5 Towns in the Berkshires and the Best Things to Do There

Towns in the Berkshires While there are plenty of wonderful things to see and do in Lenox, we always encourage our guests to travel beyond the borders of our historic town and explore everything the Berkshires has to offer! There are several quaint and unique towns scattered throughout the hills, each offering something new and exciting to experience. Whether you are a lover of art, outdoor adventure, fantastic shopping, or delicious food, you’ll find a destination with everything you’re hoping to enjoy. Here are just some of our personal favorite towns in the Berkshires and activities that we highly recommend!

Looking for more of the best towns in the Berkshires, MA to experience during your visit? We’ve got you covered! Download your free copy of our Vacation Guide to the Berkshires for a full list of the best recommendations on local attractions, restaurants, museums, and more!

5 Towns in the Berkshires You Must Visit

A visit to the Berkshires is nearly wasted unless you travel from town to town and immerse yourselves in the rich culture and charming character. Take a look at some of the most popular towns in the Berkshires along with their “must-do” activities. We hope you have something to write with because you’ll definitely want to take notes on what you read!


As the site of our beautiful bed & breakfast, Lenox truly is your home-away-from-home in the Berkshires. In addition to the town’s rich history and natural beauty, visitors from all over the country flock to Lenox for the annual Tanglewood Music Festival! This summer event features the incredible Boston Symphony Orchestra and some of the world’s most talented artists, both classical and popular, for a full lineup of concerts you’ll have to see to believe. Visitors also enjoy catching their favorite shows at the Shakespeare & Company theater and wandering through The Mount’s extravagant mansion and gardens.


With a large lineup of cultural attractions, Stockbridge is the perfect example of a Berkshire countryside destination laced with never ending excitement! During your visit to Stockbridge, enjoying a meal or live entertainment at the Red Lion Inn is a must. The famous Alice’s Restaurant, now known as Theresa’s cafe, made popular by Arlo Guthrie’s song, also calls Stockbridge home. It’s a great place to indulge in warm, comforting food within a cozy setting. Stockbridge is also home to the Berkshire Theater Group! This venue is well-known for original and well-known plays and musicals. 


Also known as the heart of the Berkshires, Pittsfield promotes and initiates cultural activity to benefit the quality of life and the town’s economy! We’re sure you won’t be disappointed when you see the Herman Melville House, more commonly referred to as Arrowhead. This museum was the home of the author of the literature masterpiece, Moby Dick! It reveals what life was like during his time and how he gained inspiration from the Berkshires. The Colonial Theater, also part of the Berkshire Theater Group, is a beautifully restored early 20th-century theater. It is home to larger productions, hosting many well-known performers. 


Antiquers, unite! Sheffield may as well be called the antique capital of the Berkshires with all the fascinating antique shops you’ll find. Each summer, you’ll also want to be in town for the Sheffield Antiques Show! Nearly 30 dealers will be attending to offer their best furniture, rugs, paintings, prints, jewelry, fireplace accessories, porcelain, silver, and more directly to you.  

Great Barrington

Great Barrington, MA wasn’t ranked as the Best Small Town in America by Smithsonian Magazine for nothing! This vibrant town is home to over 70 restaurants, unique shopping opportunities, and the beautifully renovated Mahaiwe Theater. Just take a stroll through the inviting streets of Great Barrington and we’re sure you’ll find something new and fun to try!

Plan the Ultimate Berkshires Getaway With the Gateways Inn

After exploring the best towns in the Berkshires, we invite you to return to Lenox for some well-deserved relaxation in our elegant bed & breakfast. Formerly a Procter mansion, our charming inn is unlike the typical Berkshires accommodations you’ll come across. Each of our 11 guestrooms provide all the comforts and modern amenities you would hope to find in your home-away-from-home.

Towns in the Berkshires
The Miranda at The Gateways Inn

The Miranda is our largest and finest suite with antique sage walls and French Aubusson print bedding.

Guests also love to stay in the Desdemona, a romantic room close to the garden. The room also boasts relaxing beige tones and a cozy gas fireplace.

You will also enjoy convenience to our on-site restaurant, inviting lounge, and all of your favorite Lenox attractions. Ready to make memories that will last a lifetime? Book your favorite room with us today and we look forward to welcoming you to Lenox soon!

If you haven’t already, don’t forget to download your free copy of our Vacation Guide to the Berkshires! It’s a great reference for all of the best things to do during your getaway!

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Gateways Inn