The Berkshires-Historic Homes & Gardens of the Gilded Age

The Berkshires-Historic Homes & Gardens of the Gilded Age



Venture to the beautiful hills of Western Massachusetts when springtime flowers are in peak bloom. Discover why this area—the Berkshires—became the playground for Gilded Age writers and artists during visits to many of the nation’s most fascinating historic properties, including the homes of Daniel Chester French, Edith Wharton, and Herman Melville. Also see exceptional art collections at the Norman Rockwell Museum, the Clark Institute, and Mass MoCA. Other highlights include the fabulous private garden and studio of a renowned interior designer and a tour of Tanglewood.


Pricing from
Trip Type
Closer to Home, Group Travel Tour
Departure Dates
Jun 1, 2025 - Jun 6, 2025


Accommodations at The Red Lion Inn, Stockbridge
A founding member of the Historic Hotels of America program, the iconic Red Lion Inn has been welcoming travelers to the Berkshires for more than two centuries and is one of the few American inns operating continuously since before 1800. It has the distinction of hosting six U.S. presidents! The Inn has 108 individually decorated guestrooms each with its own unique New England charm, coupling old-fashioned comfort with modern amenities, all in the confines of a beautiful historic structure! Its perfect location in the heart of the quaint village of Stockbridge makes it an ideal base for exploring many of the Berkshires’ cultural and historical attractions.


Cancellation by participant must be made in writing to ISDI and is effective only upon acknowledged receipt by ISDI. There is a non-refundable registration and planning fee of $500 per person regardless of cancellation date.


  • day 1

    Welcome to the Berkshires

    Fly into Albany, New York, and board a private motorcoach to transfer to the Red Lion Inn in Stockbridge, Massachusetts. Enjoy a relaxing afternoon either strolling around quaint downtown Stockbridge or lounging in the rocking chairs on the Red Lion Inn’s front porch. Attend a welcome dinner in the antique-filled dining room at the Red Lion Inn.

  • day 2

    Illustrious Berkshires Personalities

    Begin the day with a guided tour of Arrowhead, the historic home where Herman Melville lived during the most productive years of his life and where he wrote Moby Dick. Following lunch at a local restaurant, visit the National Trust’s Chesterwood, the magnificent home and studio of Daniel Chester French, the leading monumental sculptor of the early 20th century, most famous for sculpting the seated figure of Abraham Lincoln for the Lincoln Memorial. Continue to the nearby Norman Rockwell Museum, housing the world’s largest collection of Rockwell’s work, and enjoy a docent-led tour of his preserved studio. Rockwell lived in Stockbridge for the last 25 years of his life, where he found the subjects and inspiration for many of his illustrations and paintings. (B,L)

  • day 3

    Gilded Age Summer Retreats

    Today is dedicated to the lavish early 20th-century architectural gems that bring special renown to the Berkshires region. Begin at Ventfort Hall, a Jacobean Revival brick mansion that was built for J.P. Morgan’s sister, and has been declared an official project of “Save America’s Treasures,” a preservation initiative of the National Trust for Historic Preservation and the U.S. National Park Service. Continue to The Mount, home of noted American author Edith Wharton. This well-preserved turnof-the-century estate is filled with beautiful art and furniture and adorned with a stunning garden. Enjoy a delightful luncheon on the villa’s terrace overlooking the formal gardens. Finish your day at Naumkeag, an unparalleled 44-room Gilded-Age country estate with opulent landscaped grounds. (B,L)

  • day 4

    Contemporary and Fine Art in the Berkshires

    Spend the morning at Mass MoCA in North Adams, the largest center for contemporary arts in the United States, encompassing a vast complex of 19th-century mill buildings that have been masterfully repurposed. Enjoy an architectural tour of the complex and see highlights from the museum’s collection. Following lunch, continue to the Clark Art Institute. See the exquisite Clark Center designed by Tadao Ando and take a guided tour of the museum’s gallery highlights. The collection spans styles and centuries, ranging from Renaissance European works to American decorative arts pieces. (B,L)

  • day 5

    Bunny Williams’ Glorious Garden

    Drive to Falls Village, Connecticut to the home of renowned interior designer Bunny Williams. Enjoy a tour of her stunning private garden led by her personal gardener. Stop by Ms. Williams’ 100 Main, a home goods store filled with high end crafts by talented local artists. Enjoy a delicious lunch in a historic inn. This afternoon, tour Tanglewood, the summer home of the Boston Symphony Orchestra and the crown jewel of the Berkshires music scene. While Tanglewood will not yet be open for the season, the National Trust will tour the exquisite grounds and learn the history of its marvelous music halls. This evening, attend a festive farewell dinner in one of the area’s best restaurants. (B,L,D)

  • day 6

    Shaker Village

    Depart for the Albany airport stopping along the way at the Hancock Shaker Village, a living, working museum set on 1,200 acres of farm, woodland, and pasture. The museum is home to amazing architecture, most notably the enormous round stone barn, which is a testament to Shaker design and innovation. Arrive at the Albany airport in time to catch mid-afternoon flights home.

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