These Are the Best Things to Do in the Berkshires with Kids

A lake in Lee, MA
Photo by goofyfoottaka/Shutterstock

A three-hour road trip is a doable distance with kids. Right before the kids reach their breaking point, you arrive at your destination. Three hours is all it takes to drive from NYC to the Berkshires, and when kids realize that the best things to do in the  Berkshires include eating ice cream, they will be all in!

If you’re looking for a last-minute summer getaway, or planning ahead for fall, add the Berkshires to your list. And activities go way beyond ice cream. The scenery alone is worth the trip, plus the endless opportunities for outdoor family fun. It’s out of the range for day trips from NYC with a toddler, so set aside a few days and follow this guide to find where to stay and eat, and the best things to do in the Berkshires, while you’re there.

Where to Stay in the Berkshires

The sign for the Red Lion Inn in Stockbridge, MA
Photo by T photography/Shutterstock

Located in Stockbridge, MA, the historic Red Lion Inn is the last of the inns from the 1800s that is still in business in the Berkshires. Presidents have stayed there, as well as famous writers and musicians. What kids will love most about it is its outdoor pool, which is heated to 82 degrees year round! The many lodging options include rooms in the Red Lion Inn, Maple Glen (a 17-room guest house), and other houses on the property. The Red Lion’s sister property, the Briarcliff Motel, is a less expensive option. It is also great for kids, dog friendly, and guests are able to use the Red Lion Inn pool.

Other places to stay nearby:

The Holiday Inn & Fairfield Inn both have indoor pools and a complimentary buffet breakfast.

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Where to Eat in the Berkshires 

The Red Lion Inn offers indoor dining in their main dining room and tavern, and outdoor options (weather permitting).

The Bistro Box in Great Barrington has a family-friendly menu (think burgers, hot dogs, sandwiches, and salads), outdoor dining only, and games like frisbee and cornhole. Another plus: their sweet potato fries are said to be heavenly! Open until November.

Babalouie’s Sourdough Pizza, also in Great Barrington, is pizza perfection. Thin crust, and pretty much any topping you can think to add. Vegan and gluten-free options are available.

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Fun Things to Do in the Berkshires

In no particular order…

A SOCO blueberry lavender ice cream cone

Eat ice cream! SoCo Creamery is an award-winning ice cream shop in Great Barrington. From Peanut Butter Mudslide, Kookie Monster, and Blueberry Honey Lavender (pictured) to Lemon Poppy, Black Raspberry, and standards like Chocolate Chip, there are no bad choices—just too many to fit on one cone!

At High Lawn Farm in Lee, you can visit the cows to see where the milk comes from for High Lawn Farm ice cream and cheeses. Then, you can enjoy the delicious “farm-to-cone” ice cream at picnic tables on site.

Take a hike. Locals love the 1.5-mile Glen Meadow Loop at Greylock Glen in Adams. The gravel surface makes it a great hike for tykes. The Tyringham Cobble is a 2.1-mile loop with spectacular views. Have kids keep a lookout for Rabbit Rock, which is named for its animal shape. Bartholomew’s Cobble in Sheffield and the Benedict Pond Loop Trail near Great Barrington, are also good options for kids.

Hit the shops. One Mercantile in Great Barrington has beautiful items for the home, as well as special gifts for babies and kids. Its sister store, Sett, is a specialty tabletop shop. Robin’s Candy Store is fantastic—and parents will love that customers are given a toothbrush with their purchase.

Lake Garfield in Monterey, MAGo for a swim. If you pass a lake, you can likely take a dip in it. Many Berkshire lakes and beaches are open to the public. Life guards are on duty at Great Barrington’s Lake Mansfield, Monterey’s Lake Garfield, and more, through Labor Day.

Absorb some art and history. TurnPark Art Space in West Stockbridge has indoor and outdoor programs (through October) for all to explore. The Berkshire Museum in Pittsfield has an Aquarium. Open from April through December, Hancock Shaker Village is also in Pittsfield. It is the oldest working farm in the Berkshires. Trained staff demonstrate Shaker crafts, like basket- and oval-box making, blacksmithing, and weaving.

Pick-your-own fruit. The apple season begins at Windy Hill Farm in late-August. The farm usually grows 25 varieties of apples in its 7-acre orchard.

view from Monument Mountain in Great Barrington, MA

Elizabeth Siris Winchester is the Director of Content for Mommybites. She has spent much of her publishing career writing and editing for Time For Kids magazine and Scholastic. Liz is also the Marketing Manager for Sea Cliff Music, which provides music education to string students of all ages. 

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