10 Fun Things to Do in Historic Stockbridge MA on Your First Visit

Things to do in Stockbridge MA

Stockbridge is one of the most charming and beautiful towns to visit in Western Massachusetts! There is a small but lively town center and lots of fun things to do in Stockbridge MA. Come with us as we visit the historic downtown and discover all the best activities, museums, and much more.


Berkshires Travel Inspiration

1. Explore the Town Center

So many of the best things to do in Stockbridge start in the gorgeous town center! Main Street is full of life, and plenty of great cafes and local restaurants. Our favorite part about the downtown area is visiting it at different times of the year.

Whether the flowers are blooming in Spring, leaves are changing colors in Fall, or you catch a snowy winter day, it’s always a perfect time to be in Stockbridge! Park anywhere along the main strip or surrounding streets and go for a leisurely stroll through Stockbridge MA.

→ 6 Best Small Towns to Explore on a Trip to the Berkshires

Stockbridge Massachusetts

2. Grab a Drink at the Red Lion Inn

You might as well start off your trip to town at one of the most iconic places in the Berkshires! If you can believe it, the Red Lion Inn first opened as a tavern way back in 1773. By the late 19th century it expanded into a 100 guest hotel, and to this day it has still retained its colonial features.

Don’t worry, even if you’re not staying overnight at the Red Lion Inn you can still enjoy it! One of the best things to do in Stockbridge MA is to grab a drink, sit on the porch, and let the day pass you by. 

Red Lion Inn

3. Hike at Goodrich Memorial Park

Stockbridge Massachusetts has some amazing walking and hiking trails. One of our favorite spots to experience nature is Goodrich Memorial Park. Here you’ll find 3 different and unique paths that will take you around and above the Housatonic River. After parking, cross the Goodrich Memorial footbridge to start your walk. The trails are mostly flat and perfect for all ages. 

  • Mary V Flynn Trail: This path follows along the river and is a popular one for people with dogs.
  • Ice Glen: Hike up into the magical Ice Glen where you’ll be jumping over boulders and expecting fairy’s to fly past at any moment! 
  • Laura Lookout Tower: The steepest of the three hikes at Goodrich Memorial Park, the tower has beautiful views of Stockbridge and the surrounding area.  

Stockbridge MA Hike

4. Shop At the Unique Stockbridge Stores

Ready for some shopping? You’re in luck! One of the best things to do in Stockbridge MA is to peruse the shops on Main Street. You’ll find everything from jewelry and souvenir stores to local chocolate and wine! Even with new storefronts opening, Stockbridge has kept its historic charm which can be felt throughout town.

5. Visit Naumkeag in Stockbridge

Stockbridge Massachusetts is rich in history and cultural attractions. Naumkeag is a stunning public garden and historic home sitting on 48 acres. The forty-four-room gem was built in 1884 as a summer home for the former U.S. ambassador to Great Britain Joseph Choat.

Today, touring the grounds is a must when looking for what to do in Stockbridge MA. Also, if you happen to visit at certain times of the year you can book ahead and reserve tickets to the popular shows where they transform the grounds. Our personal favorite is seeing the winter lights at Naumkeag! 

Stockbridge MA

6. The Norman Rockwell Museum

Speaking of history… Did you know Stockbridge Massachusetts was home to one of the most famous American painters? Norman Rockwell spent his later years in this Berkshires town and now there is a wonderful museum dedicated to his work. 

In fact, the Norman Rockwell Museum has the world’s largest collection of his paintings! You may recogine one in particular on your trip to the museum. Norman Rockwell painted Main Street in Stockbridge in 1967 which has become one of his most iconic pieces. 

→ If you’d like to see more of The Berkshires best museums make sure to check out The Clark Art Institute and Hancock Shaker Village!

Norman Rockwell Museum Stockbridge MA

7. Stroll through the Berkshire Botanical Gardens

If you couldn’t tell already, there is an abundance of great nature activities in Stockbridge Massachusetts. One of our absolute favorite places is the Berkshire Botanical Garden! The 24-acre property is filled with unique garden areas and dozens of endless types of colorful flowers!

In addition to hosting weddings and private events, the Berkshire Botanical Gardens has workshops, classes, and numerous exhibits. If you’re visiting Stockbridge NA in the Fall don’t miss the annual Harvest Festival.

Berkshire Botanical Gardens

8. See a Performance With Berkshire Theatre Group 

One of the best things to do in Stockbridge MA in the summertime is to see a performance with Berkshire Theatre Group. The Unicorn Theatre and the Fitzpatrick Main Stage are both located in Stockbridge Massachusetts, while there is also the Colonial Theatre in Pittsfield. From plays to concerts and even movie premiers, a summer night with the Berkshire Theatre Group is the way to go!

What to Do in Stockbridge MA

9. Visit Chesterwood in Stockbridge MA

Like Rockwell and Choat, Stockbridge MA had another famous resident! The summer home of sculptor Daniel Chester French is on full display here as a beautiful museum and sculpture garden. Spending the afternoon at Chesterwood is such an interesting activity if you’re looking for what to do in Stockbridge MA.

Chesterwood Stockbridge MA

10. Kayak the Stockbridge Bowl

Also known as Lake Mahkeenac, the Stockbridge Bowl is a fun place to go swimming during summer in the Berkshires. Another one of the best things to do in Stockbridge MA is to kayak out on the lake. Also, make sure to see it from above at Olivia’s Overlook!

Stockbridge Bowl

Have any questions on Stockbridge Massachusetts or want to share your own favorite things to do in Stockbridge MA? Leave us a comment below! 

Safe Travels,
Brigitte & Jake

 Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar


Where to Stay in the Berkshires

Ultra Luxury – Miraval Berkshires Resort & Spa – Take in some luxury in this historic Wyndhurst Mansion turned resort. Enjoy golfing, spa treatments, and views of the beautiful Berkshire countryside. 

Fun Vacation – Courtyard by Marriott Lenox – Just a quick drive from downtown Lenox, this is the perfect spot to relax after a fun day of exploring. While there are plenty of historic hotels and Airbnb’s in the area, we enjoyed having the modern amenities and swimming pool at the Courtyard by Marriot.

Bed & Breakfast – Chambery Inn – This beautiful bed and breakfast is situated out in the countryside of Lee, but still close enough to walk to local restaurants and shops. You’ll also be just a few miles from attractions such a Tanglewood and Butternut Ski Resort.

Historic Hotel – Red Lion Inn – This historic hotel is a landmark in the town of Stockbridge. Stroll through town which is right at your doorstep, or simply watch the day pass you by while sipping on drinks on the front porch.

For more places to stay in the Berkshires you can explore the latest prices here!


USA Travel Planning 

Rental Car: We use Discover Cars when traveling. Consider renting a car in one city and dropping it off in another for an epic road trip! 

 Flights: We always find great flights using Skyscanner and Kayak. This way you can plan your trip around the cheapest and most direct routes.

 Accommodation: Compare multiple sites to get to the best deal such as Booking.com and Agoda! Also, Hostelworld can be your go-to source if you’re traveling on a budget. 

Tours: Check out Get Your Guide for hundreds of activities around the country. Book a tour of Fenway Park in Boston, skip the line at the Empire State Building in NYC, or go on a Sea Cave Kayak Tour in La Jolla California! 

 Travel Insurance: Never travel abroad without being covered! We’ve been using SafetyWing for the last few years and they are there when we need them.

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials

USA Travel

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