Things to do in the Berkshires: Boston’s Ultimate Hideaway Haven

By: Cheryl Fenton

April 24, 2014

More than a century ago, The Berkshires were known as a warm weather haven for elite, wealthy Bostonians and New Yorkers who just “had to get away.” The rolling hills of the most western county of Massachusetts were peppered with summer cottages so huge they’d stop you in your tracks.

Now, no longer a mysterious hideout for the super rich, the Berkshires are waiting to be rediscovered. Although still home to sprawling estates and spas, today there are plenty of things to do in the Berkshires for all budgets.

The Berkshires are a popular haunt for nature lovers, offering anything and everything outdoorsy, from hiking, biking and fishing to white water rafting and kayaking. There are numerous trails (including part of the 2,175-mile Appalachian), large tracts of wilderness and expansive parks. Get a bird’s eye view from Massachusetts’ highest peak Mount Greylock, at 3,491 feet.

Whether you’re climbing rocks or skipping them across a pond, Mount Washington State Forest is a natural paradise. Hike the South Taconic Trail to the 2,250 ft. summit of Alander Mountain for amazing views. Adjacent is Bash Bish Falls, Massachusetts’ tallest waterfall where the cascading water plummets 60 feet below.

Want to add a little zip to your trip? Take to the trees over mountainsides and streams with a canopy zip tour of the eastern slopes of the Berkshires. Touted as one of America’s Top 10 Zip lines by USA Today, Berkshire East Canopy Tours offers tours ranging from family-friendly to heart stopping and daring.

Boston Berkshires| The Mount

Edith Wharton’s Home “The Mount” from one of the many flower garden niches © David Dashiell 

Blending outdoor lushness with an artistic hand, the Berkshires’ historical gardens are must-sees. From Italian shade plants to fanciful French blooms, The Mount at Edith Wharton’s House earned the description “a delicate French chateau reflected in a Massachusetts pond” from novelist Henry James. There’s also Naumkeag House and Gardens, a Gilded Age mansion with 10 acres of gardens (including the famous Art Deco Blue Steps) designed by Fletcher Steele.


Once you’re done appreciating Mother Nature’s brushstroke, enjoy the region’s cultural side of more than 60 museums, theatre, dance and music venues. It’s no wonder famous names like Hollywood siren Gwyneth Paltrow, singer-songwriter James Taylor, American illustrator Norman Rockwell and authors Hawthorne, Melville and Thoreau all spent time here with their craft.

 Boston Berkshires | Ozawa Hall

Seiji Ozawa Hall at Tanglewood in Lenox © Steve Rosenthal

There’s no better place to spread out a picnic blanket, feast on gourmet goodies and listen to live music than The Tanglewood Music Center in Lenox””the summer home of the Boston Symphony Orchestra.

The Colonial Theatre is a Gilded Age architectural landmark brought back to life as a performing arts centre. With its first production (the operetta Robin Hood) opening to a sold out crowd in 1903, today you’ll find equally as rich and popular performances.

Boston Berkshires | MASS MoCA

MASS MoCA’s iconic upside-down trees and clocktower © Zoran Orlic / MASS MoCA

You can also see live music, as well as art, dance and film, at renowned Massachusetts Museum of Contemporary Arts (MASS MoCA), one of America’s largest contemporary art museums set in a sprawling 19th century mill complex of bridges, viaducts, elevated walkways and red brick facades.

Boston Berkshires | Cranwell

The 100-year-old Tudor mansion at Cranwell Resort Spa & Golf Club, located in Lenox © Cranwell Resort

And don’t forget the art of relaxation. You’ll find that on the 380 acres of The Cranwell Resort, Spa and Golf Club. One of the Northeast’s largest spas, the world-class 35,000 square-foot Spa at Cranwell boasts a 60-foot long indoor pool enclosed in a glass atrium for panoramic views.

Our partnership means you can enjoy our award winning service on Virgin Atlantic flights to New York, Boston, Los Angeles, Washington, Chicago and San Francisco and then travel onwards to 44 North American destinations with Delta Air Lines – earning miles every step of the way.

You’ll also be able to book direct flights from London Heathrow to Atlanta, Detroit and Minneapolis. Plus, you can look forward to more frequent flights from Heathrow to New York and Boston, giving you even more choice.

Have you visited the Berkshires? Where would you recommend visiting in the area? Let us know in the comments section below.

Written by Cheryl Fenton


Cheryl Fenton

A Boston native, Cheryl Fenton is no stranger to the goings on and hot spots of her favorite city. Throughout her 15-year freelance career in dining, fashion, beauty and travel, Cheryl has covered it all for local magazines and websites including Stuff, The Boston Globe, Boston Phoenix, and Boston Common. You can also find her national bylines in glossies such as Glamour, Cooking Light, and Wallpaper. In her spare time, what little there is, Cheryl strolls the city with coffee in hand, always looking for what’s next on the agenda.

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