While You’re Here

Tanglewood is, without a doubt, the primary attraction in The Berkshires. And our property is across the street from its Highwood Entrance. But there are many other performing arts venues, museums, and things to do in close proximity. There are so many different things to do that someone could spend the entire summer and not repeat. The Chesapeake Inn of Lenox is located very close to the geographical center (both east/west and north/south) of Berkshire County. This makes us an ideal location for day trips. It is because of this that we promote other attractions. And we offer packages that offer discounts for multiple-night stays.

Performance Venues

Shakespeare & Company is a professional live theatre company in the heart of the Berkshires, presenting a vibrant summer performance season featuring the works of Shakespeare in repertory with classic and contemporary plays. The Company offers one of the most extensive actor training programs by a regional theatre in the country, and is also home to an award-winning and nationally recognized theatre-in-education program.

Jacob’s Pillow is a dance center, school and performance space located in Becket, Massachusetts, in the Berkshires. The organization is known for the oldest internationally acclaimed Summer dance festival in the United States. The facility also includes a professional school and extensive archives as well as year-round community programs. The facility itself was listed as a National Historic Landmark District in 2003.

Berkshire Theatre Festival Berkshire Theatre Group was created in 2010 by the merger of two of Berkshire County’s oldest cultural organizations, Berkshire Theatre Festival founded in 1928 in Stockbridge and The Colonial Theatre built in 1903 in Pittsfield. One of the largest and most exciting arts organizations in the area, BTG oversees the development, production and presentation of theatre, music and the performing arts on multiple stages.

Williamstown Theatre Festival Since 1955, Williamstown Theatre Festival has brought America’s finest actors, directors, designers, and playwrights to the Berkshires, engaging a loyal audience of both residents and summer visitors. Each WTF season is designed to present unique opportunities for artists and audience alike, revisiting classic plays with innovative productions, developing and nurturing bold new plays and musicals, and offering a rich array of accompanying cultural events including COMMUNITY WORKS, Late-Night Cabarets, readings, workshops, and educational programs.

Barrington Stage Company (BSC) is a not-for-profit professional theatre company with a three-fold mission: to produce top-notch, compelling work; to develop new plays and musicals; and to find fresh, bold ways of bringing new audiences into the theatre, especially young people.


Arrowhead, Home of Herman Melville, author of Moby Dick

Naumkeag Estate and Gardens: With its gracious house, magnificent gardens, and panoramic views, Naumkeag is a quintessential country estate of the Gilded Age.

Norman Rockwell Museum: The Norman Rockwell Museum houses the world’s largest and most significant collection of Rockwell art. Norman Rockwell Museum presents, preserves and studies the art of illustration and is a world resource for reflection, involvement and discovery inspired by Norman Rockwell and the power of visual images to shape and reflect society.

Edith Wharton’s Mount: The Mount is a National Historic Landmark and cultural center that celebrates the intellectual, artistic, and humanitarian legacy of Edith Wharton. We engage a diverse audience by providing context to Wharton’s life and achievements through our interpretive and public programs, and preservation of her historic estate.

The Clark: In 1950 Sterling and Francine Clark chartered the Sterling and Francine Clark Art Institute as a home for their extensive art collection. Opened to the public in 1955, the Clark has built upon this extraordinary group of works to become one of the most beloved and respected art museums in the world, known for its intimate galleries and stunning natural environment.

Williams College Museum Of Art: Williams provides students opportunities for a variety of expression in the arts—from music, performance, and literature to the visual arts and dance.

Chesterwood: The country home, studio, and gardens of America’s foremost public sculptor, Daniel Chester French (perhaps best known for the Lincoln Memorial).

Hancock Shaker Village: Hancock Shaker Village brings the Shaker story to life and preserves it for future generations.

Ventfort Hall Mansion: Ventfort Hall is an imposing Jacobean Revival-style mansion built in 1893 for Sarah Morgan, the sister of J. P. Morgan. Designed by the architects Rotch & Tilden, it is located in Lenox, Massachusetts. Listed on the National Register of Historic Places, and declared an official project of “Save America’s Treasures,” a Millennium program of Hillary Rodham Clinton and the National Trust for Historic Preservation, Ventfort Hall is the home of The Museum of the Gilded Age.

Frelinghuysen Morris House & Studio: Visit the home of American Abstract Artists George L.K. Morris and Suzy Frelinghuysen, set on a 46-acre estate in the heart of Lenox, Massachusetts. View their paintings, frescoes, and sculpture, experience their exquisite collection of American and European Cubist Art.

Mass MoCA: MASS MoCA is one of the world’s liveliest centers for making and enjoying today’s most evocative art. With vast galleries and a stunning collection of indoor and outdoor performing arts venues, MASS MoCA is able to embrace all forms of art: music, sculpture, dance, film, painting, photography, theater, and new, boundary-crossing works of art that defy easy classification.

Berkshire Scenic Railway Museum: Its mission is to preserve the history of railroading, particularly in the Berkshire Hills of Western Massachusetts.