6 Best Sights in The Berkshires, Massachusetts

The Berkshire cottage of Joseph Choate (1832–1917), an influential New York City lawyer and the ambassador to Great Britain during President William McKinley's administration, provides a glimpse into the Gilded Age lifestyle. The 44-room gabled mansion, designed by Stanford White and completed in 1887, sits atop Prospect Hill. Its many original furnishings and artworks span three centuries; the collection of Chinese porcelain is particularly noteworthy. The meticulously kept 8 acres of formal gardens, a three-decade project of Choate's daughter, Mabel, and landscape designer Fletcher Steele, alone make this site worth a visit. Creative use of the property now includes a Winter Lights display, with over 200,000 twinkling LED lights; a Halloween-inspired pumpkin trail and haunted house; live music nights with picnics; and a springtime Daffodil Festival.

This 1902 mansion with myriad classical influences was the summer home of novelist Edith Wharton. The 42-room house and 3 acres of formal gardens were designed by Wharton, who is considered by many to have set the standard for 20th-century interior decoration. In designing the Mount, she followed the principles set forth in her book The Decoration of Houses (1897), creating a calm and well-ordered home. To date, nearly $15 million has been spent on an ongoing restoration project. Summer is a fine time to enjoy the informal café and occasional free concerts on the terrace. Guided tours take place during regular hours, the private "ghost tour" after hours, and noteworthy authors make regular visits to discuss their latest books.

Literary fans (and those particularly fond of Moby-Dick) will want to visit this historical 18th-century house where Herman Melville lived and wrote his most famous works. After viewing all the exhibits, take a walk around the meadow that boasts over 100 species of wildflowers, hike a trail, or just enjoy the majestic view of Mt. Greylock, the inspiration for Melville's white whale.

Tours on the hour.

For 33 years, this was the summer home of the sculptor Daniel Chester French (1850–1931), who created The Minute Man in Concord and the Lincoln Memorial's famous seated statue of the president in Washington, D.C. Occasional tours are given of the house, which is maintained in the style of the 1920s, but the real prize is the studio, where you can view the casts and models French used to create the Lincoln Memorial. The beautifully landscaped 122-acre grounds make for an enchanting stroll or bucolic picnic.

This modernist property on a 46-acre site exhibits the works of American abstract artists Suzy Frelinghuysen and George L. K. Morris, as well as those of their contemporaries, including Pablo Picasso, Georges Braque, and Juan Gris. In addition to the paintings, frescoes, and sculptures on display, a 57-minute documentary on Frelinghuysen and Morris plays on a continuous loop. Tours are offered on the hour—just be aware that it's a long walk to the house. Painting demonstrations and workshops occasionally take place.

Built in 1893, Ventfort Hall was the summer "cottage" of Sarah Morgan, the sister of financier J. P. Morgan. Lively tours offer a peek into the lifestyles of Lenox's superrich "cottage class." The museum's temporary exhibits explore the role of Lenox and the Berkshires as the era's definitive mountain retreat. Victorian high tea served during guest lectures and workshops is among the highlights.