Music, Art, Theatre and More!
This trip offers a unique juxtaposition of historic inns, fine dining and modern and contemporary art and performing arts, all set within the scenery of the charming Berkshire Mountains. Beginning at the historic Red Lion Inn in Stockbridge, you will be taken to major Berkshires landmarks including Tanglewood, the Norman Rockwell Museum, the Clark Art Institute, Jacob’s Pillow and the Williamstown Theatre Festival as well as newer treasures like MASS MoCA, the Barrington Stage Company and the Theatre Festival Cabaret.
Experience the quintessential Berkshires vacation with towns such as Lenox, Stockbridge, Great Barrington and Williamstown and connect with the culture, beauty and history of one of the most unique areas of the world. It will be one of the favorite summer trips you ever take.
Most of our travelers see four plays during their stay in the Berkshires. Featuring world-premiere comedies and musicals as well as traditional performances, there is always a range of high-level plays from which to choose. The most well known venue is the Williamstown Theatre Festival, which, since 1955, has brought America’s finest actors, directors, designers and playwrights to the Berkshires. From Bradley Cooper and Neil Patrick Harris to Blythe Danner and Matthew Broderick, WTF has played host to well known Hollywood actors. The fastest growing art venue in the Berkshires, and one which you will thoroughly enjoy, is Barrington Stage, recently lauded as a ‘jewel’ by The Boston Globe and as ‘one of America’s top regional musical-comedy producers’ by The Wall Street Journal. Barrington Stage gained national prominence with the world premiere of The 25th Annual Putnam County Spelling Bee, a runaway hit musical that later moved to Broadway and won two Tony Awards. After most performances, we can arrange for you to actually chat backstage with the performers.
Adding to the theatre options is Shakespeare & Company, one of the world’s best recognized performers of the Bard’s works, both as initially presented and with more modern interpretations. For dance aficionados, there are few more welcoming places to see high-quality dance performances than at Jacob’s Pillow, the longest-running summer dance festival in the world.
The Berkshires is also home to a number of elite art museums. A staple of the Berkshires, the Norman Rockwell Museum, houses the world’s largest and most significant collection of Rockwell’s work, including 988 original paintings and drawings (with many of his highly entertaining Saturday Evening Post covers). A resident of Stockbridge for the last 25 years of his life, Rockwell’s studio is located within the museum site and features original art materials, his library, furnishings and personal items.
Opened to the public in 1955, The Clark has become one of the most beloved and respected art museums in the world, known for its intimate galleries and stunning natural surroundings. The Clark, which sits on unique 140 acre grounds, features European and American paintings, sculpture, prints, drawings and decorative arts from the Renaissance to the early twentieth century. The collection is especially rich in French Impressionist and Academic paintings, British oil sketches and the work of American artists Winslow Homer, George Inness and John Singer Sargent.
With more than 250,000 square feet of exhibit space in what was once an electric components manufacturing facility, MASS MoCA is one of the largest centers for visual contemporary art in the U.S. Exhibits focus on large-scale, immersive installations that would be impossible to realize in conventional museums.
Not to be outdone by its more famous neighbors, the Williams College Museum of Art has blossomed over the past two decades to become a must-see for art tourism in the Berkshires. The WCMA is a vibrant center for the arts at one of the premier art and art history colleges in the country. All of our museum visits come with private guided tours.
Music also plays a critical role in our Berkshires summer trip. Tanglewood is a Berkshires landmark and the famed summer home of the Boston Symphony Orchestra, and we always get great seats. The 524-acre grounds include the Tanglewood Music Center and Seiji Ozawa Hall, two of the top ranked concert halls in the world, and has played host to legendary acts including James Taylor, Leonard Bernstein, Yo-Yo Ma and the famed Tanglewood On Parade performance with the Boston Pops each August.
And you can’t miss Cabaret at the Williamstown Theatre Festival. A late night, high-energy performance by actors, stagehands and talented interns from WTF is a fun and unforgettable evening!
Experiencing great destinations also means experiencing the natural beauty of the area. The Berkshires in the summer is unparalleled when it comes to opportunities to enjoy and explore the outdoors. From trail walks and garden tours to more demanding hikes, the Berkshires accommodates all levels of outdoor adventure. The Berkshires summer trip can include guided hikes, tee times at highly-rated golf courses and tours of famous gardens. But we also want to make sure you have your own free time to do a little of your own exploration in these beautiful country surroundings as well.
The historic Red Lion Inn, the chic and modern industrial feeling Porches Inn or Tourists, or a couple of smaller, quaint New England inns are part of any stay. We ensure that each spot has top-notch relaxation space. From rocking chairs on a front porch to spacious living rooms with a library, there is always the opportunity to relax, enjoy a drink and take in the views.
Of course, what’s a great vacation without great food? Berkshires dining is all about locally-sourced cuisine with a focus on farm-to-table dining. The Berkshires trip includes reservations at entertaining restaurants. A mix of fine dining, unique eating and off-the-beaten path spots, you are treated to an insider’s tasting of every area.
Let us set up an experience to be remembered!