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Our Top 8 Berkshires Rainy Day Activities

Updated: June 11, 2024

Looking for the best Berkshires Rainy Day Activities? There's nothing more disappointing than an unexpected rainy day when you're only visiting the Berkshires for a short period of time. Luckily, there's plenty of indoor fun to be had at any of these unique things to do in the Berkshires! Check out our list of our Favorite Top 8 Rainy Day Activities For The Berkshires, and see all the great indoor activities that the Berkshires have to offer. 

1) Shopping on Main Street, Great Barrington!

Rain or shine, Main Street, Great Barrington has a high concentration of beautiful, unique stores that you won't find anywhere else. You won't want to miss visiting us at Fluff, where our soft, cozy collection of alpaca and cotton clothing, and our adorable home goods collection, has something for everyone. The best sales pitch is just touching all of our luxuriously fluffy items! 

Outside of Fluff, the walkability and proximity of stores on Main Street and nearby Railroad Street makes this an easy, fun activity as long as you remembered your umbrella or rain coat. And if you didn't, you can always buy one! 

Check out our list of favorite restaurants and activities around Great Barrington here.

2) Bowling at Cove Bowling and Entertainment in Great Barrington

The dude abides [with rainy day bowling]. One of the inspirations for 1998 cult classic The Big Lebowski, Cove Bowling is a great way to have fun with the whole family. This retro-chic bowling alley features great food, a bar with pool tables, and of course, bowling. 

Top 8 Berkshires Rainy Day Activities Norman Rockwell Museum

3) Visit The Norman Rockwell Museum and Red Lion Inn in Stockbridge, MA

The Berkshires are synonymous with the classic work of Normal Rockwell, who spent the last portion of his life in Stockbridge, MA. The Normal Rockwell Museum houses the largest collection of Rockwell's work, and often hosts exhibits featuring the work of other talented artists. It's so easy to spend an afternoon losing yourself in the beautiful art here.

Featuring prominently in Rockwell's Stockbridge pictures is the Red Lion Inn, a historic hotel that dates back to the 18th century. It features traditional New England-style decor with antique furnishings and cozy guest rooms. The inn also offers several dining options, including a farm-to-table restaurant, a tavern, and a cafe, and it's a popular destination for tourists visiting the Berkshires region.

4) Treat Yourself to a Spa Day

Pamper yourself at one of the many local spas in the area. Canyon Ranch, located in Lenox, MA at a converted gilded age mansion, offers a wide range of services and amenities, including fitness classes, nutrition counseling, spa treatments, and outdoor activities, all aimed at promoting health and well-being. Other local notable spas and wellness center include Kripalu Center For Yoga & Health also in Lenox, and Body & Soul Day Spa in Great Barrington. 

5) Visit MASS MoCA and the Clark Art Institute

MASS MoCA (Massachusetts Museum of Contemporary Art), located in North Adams, is one of the largest centers for contemporary art in the United States. The museum is housed in a 19th-century factory complex that has been repurposed to display modern and contemporary art in all forms, including painting, sculpture, film, and performance art. The unusual art exhibitons are sure to delight the whole family. 

In nearby Williamstown is the Clark Art Institute, a renowned art museum and research center. The museum's collection includes over 14,000 works of art, including paintings, sculptures, prints, drawings, and photographs, from a variety of time periods and cultures. In addition to its extensive collection, the museum's campus includes hiking trails, gardens, and a reflecting pool.

Top Eight Berkshires Rainy Day Activities alpaca wearing a hat drinking beer2

6) Check out the local craft beverage scene 

The Berkshires are filled with some amazing local breweries, cideries, and distilleries. Check out Big Elm Brewing in Sheffield for a cool beer at their taproom, or nearby Berkshire Mountain Distillers for a tasting of their craft liquors. 

Just across the state line in Hillsdale, New York, Roe Jan Brewing Company features an amazing selection of beers in a renovated historic space — sour beer lovers will especially enjoy their signature Emma. Just down the road, Little Apple Cidery has some of the best cider in the region, with a wide variety of tasty, sophisticated ciders for all.  

7) The Berkshire Museum and Aquarium in Pittsfield, MA

Think Metropolitan Museum of Art meets Museum of Natural History, with a Berkshires twist! The museum's collection includes over 40,000 works of art, historical artifacts, and scientific specimens, covering a wide range of subjects and time periods. The museum also hosts a variety of exhibitions throughout the year, showcasing both permanent and temporary collections.

In the same building, visitors can also see a variety of fish, reptiles, amphibians, and more at the aquarium! 

8) Visit a Gilded Age Mansion

The Berkshires are home to several magnificent mansions from the Gilded Age, also known as the "Berkshire Cottages." One of the most impressive is The Mount, the former home of American novelist Edith Wharton. Designed by Wharton herself, it's a masterpiece of architecture and interior design. The stunning Naumkeag estate, designed by McKim, Mead, and White, is another must-see, with its beautiful gardens and distinctive Shingle-style architecture.