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Bob Vila meets with Bob Berle at Elm Court in the Berkshire Hills. Berle�s great-great grandparents, Vanderbilt-Sloanes, had the home built in 1886. It expanded through several additions to become the largest shingle-style home in the United States. The original architects, Peabody and Stearns, oversaw all the additions to the home and kept it within its original character while adding some flare, like the Tudor timberwork and towers. The Vanderbilt-Sloanes liked size and when they copied a fountain from the Piazza Mattei in Rome, they increased it by about 20 times the size of the original. The grounds and surrounding gardens were designed by Frederick Law Olmsted, the landscape architect who designed Central Park in New York. The grounds beautifully transition the home into the surrounding countryside. Elm Court, named after a three hundred-year-old Elm tree in the backyard, has been the site of several historic gatherings including the 1919 Elm Court Talks that led to the Treaty of Versailles.

Bob begins his tour of cottages in the Berkshire Hills in Lenox, Massachusetts. Starting with Ventfort Hall, an Elizabethan-style mansion built in 1893 for Sarah Morgan, the sister of J. P. Morgan and recently the backdrop for the movie "Cider House Rules." This home is now the site of the Museum of the Gilded Age. Bellefontaine Mansion built in 1897 is a copy of Louis XIV's Petit Trianon; it is now the home of the Canyon Ranch Spa. Guy Lowell, who later went on to design the Boston Museum of Fine Arts (MFA), the New York City Courthouse and hundreds of private residences designed this marble four-story cottage. The next stop is at the Wheatleigh mansion. Designed by the Boston architectural firm of Peabody and Stearns, more than 150 artisans from Italy created the building's intricate carvings, indoors and out. Landscape architect Frederick Law Olmsted, designer of such grand spaces as New York's Central Park, the White House grounds, and the Great Smoky Mountains and Acadia National Parks, sculpted Wheatleigh Park from the surrounding property. Bob takes a longer stop at the Italianate Spring Lawn Mansion where the Shakespeare & Company has their home. Tina Packer, president of Shakespeare & Company, guides Bob around the Spring Lawn Mansion, pointing out the Hampton Staircase inspired by Henry VIII's home. Spring Lawn was the first residence designed by Guy Lowell. The home's outbuildings are being converted to exhibits, small theatres, and teaching areas to further the theatrical education of its visitors. The showpiece of the property is the future site of the New Rose Theatre, a replica of the 1587 Bankside playhouse, Shakespeare's theatre prior to The Globe.

Bob meets with Lynn from the Shirley-Eustis Colonial Governor�s Mansion Association. She points out the Palladian fa�ade. The house was built in the 1700s and restored to the federalist period of 1820. The home is named after Royal Governor William Shirley of the Massachusetts Bay Colony and Governor William Eustis the first democratically elected governor of the Massachusetts Commonwealth. They tour the home pointing out an Irish crystal chandelier, the wood moldings and columns, plaster cornices and other unique features of the home.

Bob travels to New York City to take a break from winter in the Brooklyn Botanical Garden, a museum greenhouse on a much larger scale.