Though the Berkshires is a crowded family retreat these days, in the nineteenth century it was the exclusive summer playground of New York’s wealthiest, including J.P. Morgan’s sister, Sarah, who hosted lavish soirées at her weekend home Ventfort Hall—now the Museum of the Gilded Age. On the first floor, check out “Les Petites Dames de Mode,” an extraordinary exhibit of 59 miniature ladies dressed in exquisitely detailed gowns and coiffed with real human hair.
Get back on Route 7 and head straight for the second-floor library of the Mount, Edith Wharton’s obsessively symmetrical estate in Lenox. Though the repository is officially closed to the public, librarians allow entrance when asked (nicely). Once inside, thumb through the 2,600-book collection, sprinkled with pressed flowers, annotations, signed copies, and 22 first editions of Wharton’s work. Grab a salad niçoise and glass of Pinot Grigio from the Terrace Café and lie out on the writer’s lavish gardens. (Just steer clear of the kinda-creepy pet cemetery on the hilltop.)