The Berkshires: A Millionaire’s Playground in Massachusetts

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What has striking views, amazing resorts, and an art scene rivaling the best in Europe? Only in the Berkshires — a millionaire’s New England playground — could so much beauty and opulence be found.

Whether you’re in need of a girls’ weekend or a romantic vacation for two, the Berkshires in Western Massachusetts is the place to go for pampering and outdoor escapades.

So, what are you waiting for?


Tour a winery…or two…or three

There’s no shortage of wineries in the Berkshires, but our top pick goes to Furnace Brook Winery in Hilltop Orchards for turning the best of New England’s apple picking season into a unique apple wine blend, combined with year-round tastings and just the right amount of seasonal adventure. Only 15 minutes from downtown Lenox, expect to find full moon hikes and bonfires throughout the year and romantic couples packages during the month of February (ahem, Valentine’s Day).


Retreat to a luxury retreat

If you’re going for the millionaire lifestyle, you better know how to treat yourself at one of the four fabulous resorts in the Berkshires. For classic European splendor, sophisticated dining, and stately Greek and Roman architecture, the Wheatleigh will feel like it’s a world away from reality. For a picturesque retreat with New England fall colors in all their glory, the Canyon Ranch Lenox is the oasis you’ve dreamed of. Flawlessly blending all inclusive luxury with healthy-living initiatives, Canyon Ranch offers private and group classes with the resort’s top chef, kayaking and snowshoeing, along with plenty of detoxing spa treatments. Who says heaven isn’t on Earth?


Art galleries, museums, shopping, oh my

The Berkshires is a mecca for the arts in all its glory. Before pursuing the many local galleries, spend an afternoon touring the Clark Art Institute, where the combination of classical European and American works will help you get an eye and appreciation for the local artists. Meanwhile, a springtime stroll through the Berkshire Botanical Garden and the Garden of the Berkshires is an absolute must for colorful floral displays, while the theatre and musical productions don’t disappoint either. For a full list of all the Berkshires arts and cultural attractions, click here.

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