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Welcome to the Berkshires!

A mix of bohemian lifestyle and culture, The Berkshires in the summer is all about the arts, outdoor recreation and cultural immersion.

With the famed arts institutions able to present summer programming in real life once again, it’s time to pack your picnics and blankets for some of the country’s top cultural enrichment. Book ahead as tickets for these outdoor performances sell out quickly. Similarly, be smart about reserving museum entrances due to reduced capacity. Always check the websites for last-minute schedule changes. For outdoor activities, kayaking, rowing on the lake and hiking in the mountains will keep you happy and fit.

Farm-to-Table Dining 

Outdoor dining surrounded by the beautiful Berkshire Mountains is an airy pleasure in the summer. The Berkshires’ acclaimed farm-to-table cuisine comes alive with berries and greens that add vibrant colors. Café Boulud at Blantyre is now a permanent residency at the luxurious Relais & Chateaux estate. Michelin-starred Chef Daniel Boulud uses fresh and local ingredients for fine dining with a menu of seasonal French classics with a New England twist. The setting is Berkshires Gilded Age, so dress your best.

Modeled after a Berkshire country home, the upscale-yet-rustic CafeADAM is a welcoming space with an ever-changing menu of farm-to-table choices and artisanal beverages. Be sure to try the local cider and beers on tap.

Away from the crowded center of the Berkshires, John Andrews Farmhouse Restaurant sits in a structure dating from the late 1700s on its original farmstead. The menu epitomizes farm-to-table, with seasonal ingredients sourced from local farms and food artisans. Chef Dan Smith’s focus is one of taste-of-place dining, ensuring that you have a truly Berkshires experience with a menu built around regional producers of the moment. A summer specialty is tempura of squash blossoms stuffed with chèvre with herbs from the restaurant’s own gardens.

Once a stagecoach relay station, The Old Inn on the Green hearkens back to New England’s past, using only candles and fireplaces to light its private dining rooms. Changing daily and determined by the day of the week, an a la carte or prix fixe menu is offered along with a special Chef’s Tasting Menu. Reserve a table here for an evening of retro romance. 

Farm-to-Table Cuisine | WhereTraveler
Farm-to-Table Cuisine (©Marcus Wallis)

Museums, History and the Performing Arts 

Indulge in the Berkshires’ wealth of entertainment, historical homes, and world-class museums as previously shuttered venues welcome visitors once again. Known worldwide, Tanglewood, Jacob’s Pillow and Shakespeare & Company are among the cultural institutions synonymous with the area. House and garden tours of the Berkshires’ “cottages” are equally in demand and provide a taste of estate life during the Gilded Age. 

Jacob’s Pillow may be minus one of their outdoor stages due to a fire in November, but the revered dance venue is back with a full program of dance greats on its main stage.

The summer home of the Boston Symphony Orchestra, Tanglewood, was sorely missed in 2020. This year, the shed and lawn will be filled with music lovers enjoying performances by both the BSO and the Boston Pops. The popular artist series resumes in August with James Taylor and John Legend. Tanglewood’s schedule is subject to change so check the website for additions and cancellations.

For fans of the Bard, Shakespeare & Company is one-of-a-kind with a season of back-to-back outdoor productions in a new amphitheater. The Williamstown Theatre Festival is a favorite for classic and new plays and musicals. Performances are scheduled in a variety of locations, including the Clark Art Institute. 

Jacob's Pillow Berkshires New York | WhereTraveler
Jacob's Pillow (©Christopher Duggan)

Recently portrayed in the documentary "Museum Town," MASS MoCA offers a distinctive setting for evocative art. In a sprawling complex of former 19th-century mill buildings, the art center has vast galleries, performing arts venues and permanent and purpose-built exhibits. An elaborate system of interlocking courtyards and passageways connects the 26 buildings.

With its nostalgic depictions of life through illustration by Berkshires resident Norman Rockwell, the Norman Rockwell Museum is the most popular cultural attraction in the Berkshires. Adults will appreciate the social commentary as espoused in Rockwell’s art, while children love the drawings. A well-timed escape from the darkness of the past year, the museum’s summer exhibits are all about fantasy. "Land of Enchantment, a Fantastical Outdoor Sculpture Exhibit," and "Enchanted: A History of Fantasy Illustration" will transport to worlds where dragons and sorcerers rule.

One of the country’s most acclaimed small museums and a pioneer in children’s programming, the Clark Art Institute offers indoor exhibits as well as the museum’s first outdoor installation, "Ground/work." The museum is noted for its collections of Impressionist, American and other art. 

Norman Rockwell Museum Berkshires New York | WhereTraveler
Norman Rockwell Museum (©Walt Engels)

Advance reservations are required for self-guided house and garden tours of the Berkshires’ Gilded Age “cottages.” The home of author Edith Wharton, The Mount, was designed by the author herself and built-in 1902 and reflects Wharton’s theories about classic European architecture adapted for an American landscape. Summer at The Mount features SculptureNow, an intriguing display of outdoor art, with artist-led tours available.

Nearby Ventfort Hall is an imposing Jacobean Revival-style mansion built in 1893 for Sarah Morgan, sister of J. P. Morgan. Inside the mansion, the Gilded Age Museum interprets the great changes that occurred in American life, industry and society during the nineteenth century.

Naumkeag, a 44-room Gilded Age “cottage” with expansive stepped gardens, shows off how the wealthy lived during the late 1800s while providing a beautiful environment for outdoor yoga and meditation. 

The Mount, Edith Wharton's Home Berkshires New York | WhereTraveler
The Mount, Edith Wharton's Home (©Kara Thornton)

Where to Stay

Wellness, inn life, and hospitality are inseparable in the Berkshires. Whether you stay at an all-inclusive resort or at a cozy inn, you’ll enjoy some of the finest relaxation and recreation in the country. To help visitors rejuvenate and de-stress, Canyon Ranch Lenox offers life-enhancing “pathways,” curated wellness programs of varying lengths. Indoor squash, tennis, racquetball and basketball courts complement daily fitness classes, hikes, lake paddles and holistic spa treatments.

Now in its first summer season, Miraval Resort & Spa is known for its mindfulness focus. Activities including aerial yoga, equine programming, hiking, biking, beekeeping and kayaking make for a diverse and indulgent experience at the expansive property. Spa programming is an integral part of the Miraval journey, combined with a culinary emphasis on balance. For visitors wishing a sample of the Miraval experience, Day Spa Passes are available.

One of only a few American inns operating continuously since before 1800, The Red Lion Inn is a member of Historic Hotels of America and appeals to Americana buffs with its Rockwell-esque front porch, classic New England lobby and traditional rooms.

On 22 acres overlooking the Berkshire Mountains and lake, the five-star Wheatleigh Hotel is a Berkshire treasure. Built in 1893, the 19-room Italianate mansion offers privacy and seclusion with a museum-like setting appointed with antiques, architect-designed furnishings and original contemporary art.

An English-Style country house originally built in the early 1800s, Devonfield Inn overlooks a meadow shaded by birch trees against a backdrop of rolling hills. Live lawn concerts at the charming inn complement popular activities, including hiking on the inn’s extensive grounds, yoga on the lawn, and a program for horseback riding. 

Red Lion Inn Exterior Berkshires New York | WhereTraveler
(Courtesy Red Lion Inn)