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

Stockbridge is one of the most charming and beautiful towns to visit in Western Massachusetts! Enjoy the small, but lively town center and so many fun things to do in Stockbridge MA. Join us in the historic downtown and discover all the best activities, museums, and much more.

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10 Fun Things to Do in Stockbridge MA 

1. Explore Stockbridge MA Town Center

So many of the best things to do in Stockbridge MA 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 Massachusetts! 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

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. To this day still retains its beauty and colonial features.

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. 

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 in this part of Stockbridge MA 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. This tower has beautiful views of Stockbridge MA and the surrounding area.  

4. Shop At the Unique Stockbridge MA 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 Massachusetts

Stockbridge MA is rich in history and cultural attractions and Naumkeag is the perfect example of that. This stunning public garden features a 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. Touring the Naumkeag 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 reserve your spot for something special. There are popular shows where they transform the grounds for the holidays. Our personal favorite is seeing the winter lights at Naumkeag! 

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 the artists paintings! You may recognize one in particular on your trip to this Stockbridge MA museum. Norman Rockwell painted Main Street in Stockbridge in 1967 which has become one of his most iconic pieces. 

→ Want to see more of the best museums in the Berkshires? Make sure to check out The Clark Art Institute and Hancock Shaker Village.

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 MA in the Fall don’t miss the annual Harvest Festival.

8. See a Show in Stockbridge MA 

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.

The Colonial Theatre in Pittsfield is also a great place to see a show. From plays to concerts and even movie premiers, a summer night with the Berkshire Theatre Group is the way to go!

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.

10. Kayak the Stockbridge Massachusetts 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!

More Things to do in Stockbridge MA

We hope this blog gave you some great ideas for what to do in Stockbridge Massachusetts. The town has so many great walking trails, historic sites, and cultural activities to experience. 

It’s no surprise that Stockbridge MA is known as one of the best places to visit in the Berkshires! Use this is a rough guide to find your own hidden gems when visiting.

Have any questions on this article or want to share your 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!

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New England Travel Planning 

 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. 

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! 

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 Scenic Boat Tour in Portland Maine! 

 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! 

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