Massachusetts

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.

By Aimee Tucker|Jun 21 2018| Print icon

Summer Weekend in the Berkshires

Red Lion Inn | Summer Weekend in the Berkshires

Credit: Aimee Tucker
Sponsored by Red Lion Inn 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.

5 REASONS TO PLAN A SUMMER WEEKEND IN THE BERKSHIRES

HISTORICAL HOSPITALITY

Red Lion Inn | Summer Weekend in the Berkshires

Red Lion Inn | Summer Weekend in the Berkshires

Credit: Aimee Tucker
The Red Lion Inn in Stockbridge | Summer Weekend in the Berkshires
Credit: Aimee Tucker 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.
Red Lion Inn

Red Lion Inn

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

Red Lion Inn

Credit: Aimee Tucker
The Red Lion Inn’s heated pool, open year-round | Summer Weekend in the Berkshires
Credit: Aimee Tucker

THE GREAT OUTDOORS

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.
Berkshire Botanical Garden

Berkshire Botanical Garden

Credit: Aimee Tucker
Berkshire Botanical Garden | Summer Weekend in the Berkshires
Credit: Aimee Tucker 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.

HISTORY & CULTURE

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.
Chesterwood

Chesterwood

Credit: Aimee Tucker
Daniel Chester French’s Chesterwood | Summer Weekend in the Berkshires
Credit: Aimee Tucker
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.
Chesterwood

Chesterwood

Credit: Aimee Tucker
The scale model of Seated Lincoln at Chesterwood | Summer Weekend in the Berkshires
Credit: Aimee Tucker

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.
Summer Weekend in the Berkshires

Tanglewood | Summer Weekend in the Berkshires

Credit: Aimee Tucker
Tanglewood | Summer Weekend in the Berkshires
Credit: Aimee Tucker

LOCAL FLAVORS

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).
Widow Bingham's Tavern at Red Lion Inn

Widow Bingham’s Tavern at Red Lion Inn

Credit: Aimee Tucker
Widow Bingham’s Tavern at the Red Lion Inn | Summer Weekend in the Berkshires
Credit: Aimee Tucker
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.)
Six Depot | Summer Weekend in the Berkshires

Six Depot | Summer Weekend in the Berkshires

Credit: Aimee Tucker
Iced cold-brew coffee and a buttery croissant from Six Depot | Summer Weekend in the Berkshires
Credit: Aimee Tucker
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. 

Aimee Tucker

Aimee Tucker is Yankee’s senior digital editor. A lifelong New Englander and Yankee contributor since 2010, Aimee has written columns devoted to history, foliage, retro food, and architecture, and regularly shares her experiences in New England travel, home, and gardening. Her most memorable Yankee experiences to date include meeting Stephen King, singing along to a James Taylor Fourth of July concert at Tanglewood, and taking to the skies in the Hood blimp for an open-air tour of the Massachusetts coastline.

More by Aimee Tucker

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  1. I just love Yankee Magazine so informative, wonderful travel suggestions and great recipes. My son loved the gift of Yankee Magazine!

    Reply

  3. You mention the most obvious places. Down the street from the Red Lion Inn is Mission House and Naumkeeg, a 44 room gilded age home that has tours 7 days a week through the summer. For dinner head to Sheffield at The Bridge restaurant.

    Reply

    1. Hi Gail. Thanks for your comment. It’s always a struggle to fit as much as possible into a short weekend visit. I did mention Naumkeag, but opted to explore Chesterwood this time around. Hopefully I will get to it next time. Thanks for the extra tips, and have a great day!

      Reply

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