NEW ENGLAND

WESTERN MASSACHUSETTS & THE BERKSHIRES

Head west from Boston into Western Massachusetts and we will unveil a charming haven of countryside known as The Berkshires, renowned for its cultural attractions and pastoral beauty. The region borders Connecticut, New York and Vermont and boasts fine museums and galleries, film and historic sites, and food and wine festivals. There are picturesque orchards, storybook country inns and bustling farmers’ markets. Despite its Sleepy Hollow vibe, a Berkshires vacation is far from sedate, offering instead the chicest of pastimes. Listen to the Boston Symphony Orchestra in its summer home at Tanglewood. Shop at upscale boutiques and artist studios in Great Barrington. Dine on James Beard-nominated cuisine. Take in a Shakespearean theater troupe performance. And spend an afternoon fixating on the artwork at the contemporary MASS MoCA.

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Our New England experts are ready to plan your next great adventure. Use the button below or call 866-686-2106 to speak with someone from our team. We can’t wait to hear from you!

HIGHLIGHTS OF WESTERN MASSACHUSETTS

THE HEART OF THE BERKSHIRES – LENOX, STOCKBRIDGE & ENVIRONS


THE HEART OF THE BERKSHIRES – LENOX, STOCKBRIDGE & ENVIRONS

Lenox is the center and cultural heart of a Berkshires vacation, and having a local expert help guide the way is invaluable. Otherwise, one might be tempted to porch-sit all day long, daydreaming about calling this gracious countryside home. Yet venture out you must, to the Tanglewood Music Festival, to locally sourced eateries, to A-listed spa resorts and more. Nearby, Stockbridge’s wide Main Street doesn’t even sport a stoplight, a delightful omission in modern life. Iconic New Englander Norman Rockwell lived and worked here for a significant chunk of time at the end of his life and found pleasure in his own porch-sitting afternoons at the historic Red Lion Inn. Rest assured, if it’s peace and tranquility you’re after, a Lenox and Stockbridge vacation is sure to deliver.

WHAT WE REVEAL
Our ventures into the Heart of the Berkshires pave the way into the region’s genteel historic air. Visit Stockbridge’s quaint Red Lion Inn, home to a famous teapot collection with hundreds from all over the world. Listen to stories about the town’s founders as you visit the First Church. Our local experts take you to Chesterwood, home to Daniel Chester French, the sculptor of the seated Lincoln in Washington, DC. Spend a day with a private guide on a Berkshires cottage tour – this area is known as the “inland Newport” – during which you’ll see the homes of Andrew Carnegie, Harley Proctor of Proctor & Gamble Co., George Westinghouse, the Vanderbilts and more of America’s aristocracy. Take in an evening of classical music at the Tanglewood Music Shed, an indoor amphitheater and distinctly Berkshires experience. Lunch and shop in Lenox, a quintessential New England town with an eclectic collection of artistic and next-level shops. Hancock Shaker Village is a treat, comprised of 25 historic buildings showcasing the life of the Shakers – the Round Stone Barn is a must-see. For nature-lovers, join our guide on the best sections of the Appalachian Trail through the Berkshire Mountains. And what’s a New England vacation without maple syrup? Taste the sweet nectar – and other farm bounty – for yourself at the 18th-century Bidwell House.

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> Vermont
> Boston & Cape Cod

THE NORTHERN BERKSHIRES


THE NORTHERN BERKSHIRES

The Northern Berkshires make up an artsy and pastoral northwestern corner of Massachusetts and southeastern Vermont, sandwiched between Mount Greylock and Vermont’s Green Mountains. It’s little wonder urbanites set their sights on this pretty-as-a-picture, year-round playground, whether to hike, bike and cross-country ski, or step back in time to the age of Edith Wharton and Norman Rockwell. Forward-thinking institutions like the Massachusetts Museum of Contemporary Art (MASS MoCA) neighbor historical sites from the American Revolution and Civil War. Preppy college campuses at Williams and Bennington offer an erudite vibe to hipster coffee shops and open-mic nights.

WHAT WE REVEAL
Our local art experts recommend MASS MoCA, the Bennington Museum, the Williams College Museum of Art and the Clark Art Institute for art lovers on a Northern Berkshires vacation. While the latter is known for its extraordinary collection of Impressionist and Renaissance paintings and works by Frederic Remington and Winslow Homer, you’ll be just as wowed by the museum’s 130 idyllic acres of lawns and meadows. Perhaps your Northern Berkshires vacation will coincide with the Williamstown Theatre Festival, an annual gathering of the country’s finest actors, directors and playwrights. Visit Robert Frost’s burial site in the cemetery adjacent to the Old First Church in Bennington, deemed “Vermont’s Sacred Acre” in 1937. And we’ll lead you to superb hiking on Mount Greylock, verdant golf courses, whitewater rafting and horseback riding come summer. Come winter, there’s snowshoeing and skiing, both alpine and Nordic, and unmistakable appeal of New England village-style winter festivals.

COMBINE WITH
> Vermont
> Boston & Cape Cod

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