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How To Spend A Beautiful Weekend In The Berkshires

Posted on June 17, 2020Written by Linda Beach
Updated on June 17, 2020

Weekend Berkshires

Published by Travel Awaits
Written by Sandi Barrett

Museums, Concerts, Galleries and more await your visit

Photo Credit Colin D. Young/Shutterstock

Spending a luxurious weekend in the Berkshires surrounded by classic elegance and verdant vistas is the perfect soul-rejuvenating getaway. Located in the Green Mountains of western Massachusetts, the Berkshires encompass the towns of Lenox, Amherst, Stockbridge, North Adams, Lee, and Great Barrington. In the Berkshires, art, culture, and history come together with the gifts from Mother Nature’s bountiful gardens.

Museums, concerts, art galleries, exquisite cuisine, and luxury stays plus quiet nature walks, yoga retreats, and wellness spas will make your weekend in the area quite zen. A getaway in the Berkshires is the perfect mind-and-body retreat.
Here’s how to spend your time in the area.

Enjoy A Concert at Tanglewood

Grab a blanket or chairs, a picnic basket, and your best friend, and find a spot on the lawn at Tanglewood, the Boston Symphony Orchestra’s summer home. Tanglewood offers a wide variety of concerts, from Judy Collins and Arlo Guthrie to Mozart and Debussy. The sound and visual systems are state of the art, transforming the lawn seating into a magical concert under the starlit sky.

More than just a performance center, Tanglewood offers Summer Sundays during July and August. Summer Sunday activities include guided nature walks, orchestra instrument demonstrations, a food and beverage tent, a children’s craft tent, and a Sunday Showcase. The showcase takes place at the Theatre-Concert Hall at 12:30 p.m. and includes a variety of performances, demonstrations, and informal talks. Docents offer a free hour-long walking tour of the Tanglewood campus on which you will learn about the institution’s history and visit several of the buildings on-site. The grounds are open to the public off-season for self-guided tours.

Go On A Zen Kripalu Yoga Retreat

Famous for their personalized retreats, the Kripalu Center for Yoga & Health allows you to commune with the beautiful nature of the Berkshires at a very personal level. Plan your relaxing, rejuvenating retreat by selecting from the variety of workshops, activities, and classes. Focused retreats and classes include Yoga And Meditation, Quieting Your Inner Critic, Digital Detox, Massage, Forest Bathing, and Outdoor Hiking And Yoga. If you crave a zen experience, Kripalu will guide you to your personal nirvana.

View Iconic Norman Rockwell Illustrations

Step back in time as you meander through the Norman Rockwell Museum. You will see students perched on stools sketching the iconic Saturday Evening Post covers. With rotating exhibits by contemporary artists anchored by Rockwell’s illustrations, the museum highlights both the classics and the up and coming. The grounds are decorated with gardens featuring Rockwell’s son’s sculptures. It is a wonderful venue for a picnic — bring your sketchpad or camera and spend a lazy afternoon enjoying the views.

Appreciate Edith Wharton’s Literary Legacy

Edith Wharton was the first woman to receive the Pulitzer Prize for Fiction. The author of The Age of Innocence, Wharton didn’t conform to societal norms. She championed rights for women when, in the late 19th century, women were only expected to marry. Very few achieved personal independence and wealth.

Wharton’s country estate, The Mount, is now an interactive museum. Visitors are treated as guests; on one of the most popular tours, you’ll learn about Wharton’s legacy and the general workings of the estate. Tours include a house tour, garden tour, backstairs tour, and even a ghost tour. Private library tours and a seasonal literary round table round out the offerings.

Visit Emily Dickinson’s Birthplace

At Amherst College is the Emily Dickinson Museum, which comprises the poet’s birthplace (The Homestead) and her brother Austin’s home (The Evergreens). An hour-long guided tour of several of the rooms in the homes will give you a peek at the poet’s life. “Hope is the thing with feathers” is a quick read to get you in the poet’s state of mind before you go. The museum also offers a private studio session where you can spend up to 2 hours in Dickinson’s bedroom. You are provided with a writing desk where you can absorb her artistic spirit. The experience would be a unique and fascinating gift for the artist who has everything. The house is a quiet spot where you can dream of a bygone era and bathe in the poet’s creativity.

Head To The Massachusetts Museum Of Contemporary Art

The Massachusetts Museum of Contemporary Art, known as MASS MoCA is home to thought-provoking, boundary-breaking art. The art installations are the basis for deep conversations. They reflect current events, cultural conceptions, and inspirational quirkiness. The art depicted departs from tradition, producing interesting and sometimes alarming results.

Where To Eat In The Berkshires

Locally sourced, seasonal menus paired with exquisite wines and traditional cocktails are a perfect ending to a day steeped in culture and history.

The Conservatory

The Conservatory at Blantyre offers an exceptional dining experience. Enjoy a five-course tasting menu with wine pairings that include the likes of northern prawn ravioli and heritage lamb loin. Berkshire duck galantine and Northeast Family Farms filet mignon are also on offer. The gastronomic pleasures are served in classic casual luxury. At The Conservatory, children must be at least 16 years old to dine.

The Portico

The Portico at the Wheatleigh Hotel delivers high-end European-style dining. With only eight tables gracing the glass-walled dining room, reservations are required. Your intimate dining journey begins with a choice between Chef Jeffrey Thompson’s six-course tasting menu and a prix fixe menu. The elegant offerings are made from fresh, local ingredients prepared with a French flair. Menu items include Pointy Snout Ossetra caviar, Perigord black truffle, and foie gras, among other gastronomic delights.

Where To Shop In The Berkshires

Many artists are drawn to the natural beauty and charm of the Berkshires. Art galleries dot the quaint New England downtowns and back roads. Berkshire Visual Arts provides a list of these local galleries along with a brief description of what you will find in each shop. The galleries specialize in fine art, ceramics, modern art, and a treasure trove of other media.
The Holsten Galleries is one of the few East Coast galleries to carry museum-quality Chihuly glass. Studio 21 South is a cooperative artist space that offers several galleries for a variety of artistic finds. Many of the galleries have odd or appointment-only hours, so be sure to check online to avoid disappointment.

Where To Stay In The Berkshires

You will find a wide range of accommodations in the Berkshires. The two listed below best represent the casual luxury of the area.

The Porches Inn

Staying at a quintessential country house in the Berkshires will immerse you in the relaxed vibe of the area. The Porches Inn is just that sort of charming house, a painted lady with a classic feel and first-class amenities. Stake out a rocking chair on the wide porch and enjoy the picturesque view. After dinner, stroll down to the bonfire pit and enjoy a cocktail while you discuss your day’s adventures with like-minded guests.


Tudor-style luxury is the hallmark of Blantyre. Here you will experience refined elegance paired with exemplary service, providing the perfect romantic weekend getaway. Choose from the Manor House, the Carriage House, or the Cottages for a memorable stay. Blantyre also offers an exquisite Champagne Salon. Sip remarkable Champagne in the intimate stone cellar while dining on seasonally inspired small plates for a one-of-a-kind experience. You must make a reservation at least 24 hours in advance to partake of the fruit of this particular vine.

What To Know Before You Go

A wide variety of experiences are available in the Berkshires. The suggestions in this article focus on the historic, cultural, and luxurious aspects of the region. However, you could easily plan a visit tailored to your interests that would be just as memorable. A camping and hiking trip in the beauty of nature, a family-focused cultural weekend, a photography adventure — all are within reach in the Berkshires.

However you plan your experience, the people and the scenery of the Berkshires will welcome you with open arms.

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