Best Vacation Towns in the Berkshires

“I’ve seen sunny days that I thought would never end.” Yes, Berkshire County is having its day in the sun. Just ask James Taylor, or the editors at Travel and Leisure magazine. While the region’s charming towns, cultural institutions, and farm-to-table food scene have long attracted visitors, the rustic area from western Massachusetts to the Connecticut border is now at the forefront of the global conversation, according to Travel and Leisure. The magazine recently named the Berkshires “one of the 50 best places in the world to travel in 2018.”

 

Featuring country roads, farmers’ markets, bookstores, galleries, and cultural mainstays such as Tanglewood, Mass MoCA, and the Williamstown Theater Festival, here are the top 4 vacation towns in the Berkshires.

 

Great Barrington is the Southern Berkshires’ “big” city, but it’s only big in comparison to the many villages that surround it. Located three hours from Manhattan and two hours from Boston, Great Barrington is the kind of small town where everybody knows your name but where you can still find sushi at 3 AM. The city’s cultural attractions include Barrington Stage Company, Mahaiwe Performing Arts Center, a lively downtown, a triplex movie theater, and over 55 restaurants. Outdoor enthusiasts can fly-fish on the Housatonic River, hike a nearby section of the Appalachian Trail, and climb Monument Mountain.

 

 

In the 19th century, the Vanderbilts, Carnegies, and Westinghouses summered in Lenox, building grand villas known as Berkshire cottages and turning the hamlet into the Gilded Age equivalent of the Hamptons. The arts, culture, and wellness have been a part of the Lenox for a long time. Tanglewood is the summer home of the Boston Symphony Orchestra, not to mention James Taylor. A long-time Berkshire resident, he’s peformed at Tanglewood 25 times since 1974.

 

Lenox features three world-class spas including Canyon Ranch, Cranwell Spa and Golf, and Kripalu Center for Yoga and Health. Lenox is a storybook place where vacationers can stay at Belle Époque mansions, visit the country house and studio of sculptor Daniel Chester French, Chesterwood, and top off the day with a relaxing spa experience.

 

 

Thanks to a Norman Rockwell painting, Stockbridge has one the most famous Main Streets in America. The beloved painter lived in the rural New England town from 1953 until his death in 1978. The Norman Rockwell Museum, founded in 1969, is set on 36 scenic acres and features the largest collection of Rockwell art in the world. Stockbridge boasts one of the oldest continuously operating historic inns, too. Founded in 1773, the Red Lion Inn has hosted notable guests over the years, including five presidents, Nathaniel Hawthorne, and Henry Wadsworth Longfellow.

 

 

Located in Columbia County, in New York’s upper Hudson Valley, Chatham is an eclectic small town featuring a Main Street with brightly painted brick buildings and independently-owned stores and studios like The Chatham Bookstore and Supersoul Yoga. The village’s historic highlights include the Clocktower, Union Station, and Crandell Theater, one of the country’s few independently-owned theaters showing first-run movies.

 

The real star of Chatham, however, is its idyllic country setting. Explore the region’s nature and wildlife at Ooms Conservation Area at Sutherland Pond, and end the day with a visit to Chatham Brewing. The microbrewery features a tasting room, food truck, and locally sourced food.

 

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