Chesterwood Highlighted in Yankee Magazine's New England Today Travel

5 Reasons to Plan a Summer Weekend in the Berkshires

With an abundance of culture, natural beauty, and historical hospitality, the Berkshires offer the perfect setting for a summer weekend escape.

New England Today Travel:  Berkshires Section

Aimee Tucker • June 21, 2018 

The Berkshire Hills region of Western Massachusetts has often been described as “America’s premier cultural resort,” and one visit is all it takes to understand why. Its history as a popular vacation retreat for turn-of-the-century urban elite set in motion a tradition of art and hospitality that continues to thrive here more than a century later. A visit to the Berkshires, especially in summer, is guaranteed to be one of entertainment, education, and relaxation, bolstered by beautiful scenery, fine historic inns, and delectable food. What’s not to love? Here are five reasons to plan your perfect summer weekend in the Berkshires.



There are many lodging options for visitors to the Berkshires, but the Red Lion Inn in Stockbridge is arguably the region’s oldest and most visited. Dating back to 1773, the sprawling Main Street structure is known for its authentic historic character (note the working birdcage elevator and converted telephone “booths” off the main lobby), period furnishings, variety of on-site dining options, and seasonal charms such as the crackling lobby fireplace in the winter and the wicker-strewn front porch in the summer.

History buffs love exploring the many nooks and crannies at the Red Lion Inn. | Summer Weekend in the Berkshires

This was my first visit to the Red Lion Inn in summer (Stockbridge at Christmas is a true holiday delight), and it was a wonderful to take advantage of the inn’s heated outdoor pool and alfresco courtyard dining.


Love getting closer to nature? The Berkshire Hills are a dream destination for outdoor enthusiasts. Whether it’s swimming or boating at the Stockbridge Bowl (also known as Lake Mahkeenac), hiking Monument Mountain in Great Barrington, or biking the 11.2-mile Ashuwillticook Rail Trail from Lanesborough to Adams, there are plenty of reasons to get outside.

For those who like a gentler outdoor experience, the Berkshire Botanical Garden in Stockbridge is the perfect place to stroll, relax, and literally stop and smell the flowers. Enjoy 15 acres of cultivated grounds, including a serene garden pond full of croaking frogs and acrobatic dragonflies.


Fans of history and culture are spoiled in the Berkshires, where gems such as Hancock Shaker Village in Pittsfield and top-notch art museums like Mass MoCA in North Adams (the largest museum of contemporary art in the country) and the Clark Art Institute in Williamstown draw crowds, as do the summer-homes-turned-museums of the region’s most famous writers and artists.

In Lenox, you can visit the 1902 estate and gardens of author Edith Wharton’s home, the Mount. In Stockbridge, you’ll find the museum and studio of beloved illustrator Norman Rockwell at the Norman Rockwell Museum, the 1896 estate and studio of sculptor Daniel Chester French at Chesterwood, and the 1886 estate and spectacular gardens of New York City attorney (and former American ambassador to England) Joseph Hodges Choate at Naumkeag.

Abraham Lincoln fans are especially drawn to Chesterwood for its seven-foot Seated Lincoln model on display in French’s studio. The larger Georgia-marble original at the Lincoln Memorial in Washington, D.C., is admired by an estimated six million people each year.

4.       MUSIC & THEATER

The performing arts have a long history in the Berkshires, with highlights including the Jacob’s Pillow Dance Festival (the country’s oldest summer dance festival), the Williamstown Theater Festival, and shows by companies such as the Berkshire Theatre Group and Shakespeare & Company. You also can’t mention musical performance in the Berkshires without a deep bow to Tanglewood, the summer home of the Boston Symphony Orchestra and New England’s favorite “concert with a picnic” destination since 1937. On a warm summer evening, armed with nothing more than a lawn ticket, folding chair, blanket, and cooler full of picnic essentials, you’ll find there is no better place to be in the world.


Last but never least, the food. When visiting the Berkshires in summer, be sure to come hungry. This is a place where the best farm-to-table restaurants happily mingle with cafés, roadside stands, and farmers’ markets overflowing with fresh seasonal produce.

I was delighted to have the Red Lion Inn’s many dining options just steps away (ranging from a cozy dinner in Widow Bingham’s Tavern to a sunny outdoor lunch in the courtyard to a local brew with live music in the Lion’s Den pub).

On this visit, I made sure to also visit Six Depot Roastery and Café in West Stockbridge for coffee and a leisurely breakfast; the Scoop in downtown Lenox for a dish of coffee ice cream after an hour of shopping; the Bistro Box in Great Barrington for the perfect roadside burger; and two Stockbridge mainstays, Elm Street Market and Nejaime’s Wine Cellar, for my Tanglewood picnic essentials. (I’m also a big fan of Guido’s Fresh Marketplace in both Pittsfield and Great Barrington for Tanglewood prep.)

And so ends another wonderful summer weekend in the Berkshires! As always, it’s impossible to do and see it all — but having a reason (or 10) to return is half the fun.

What are your favorite things to do when visiting the Berkshires in summer? Let us know!

This post was first published in 2017 and has been updated.