Norman Rockwell’s paintings defined small-town America, and he chose Stockbridge, Massachusetts, in the Berkshire Mountains for the studio in which he would work until the end of his life. Situated a few hours’ drive from New York City and Boston, the region comprises 30 towns in Massachusetts and Connecticut and is renowned for its fall foliage, antique shopping and outdoor recreation.
Begin in Lenox, Massachusetts, at The Mount, which was the home of 20th century author Edith Wharton. An architectural jewel and National Historic Landmark, its multiple European-inspired buildings, formal gardens and surrounding forest will be cloaked in autumn color. Tours of the 42-room home, Georgian Revival-style stables and estate take place daily and include views of ReMix, a contemporary sculpture exhibit featuring 20 large-scale contemporary works throughout the grounds. Afterward, visit downtown Lenox’s many boutique shops, including a wine shop and bar.
Don’t forget your camera. Pack a picnic and head to Mount Greylock State Reservation in Lanesborough, Massachusetts. Its namesake peak is the highest point in the state, offering stunning panoramic views of the Appalachian Trail. Experienced hikers might consider the 3.2-mile hike from Wilbur’s Clearing to the summit. Shorter, less strenuous hikes are available off the state-designated Scenic Byway.
Explore the region’s diverse cultural opportunities in Williamstown, Massachusetts, home to liberal arts beacon Williams College. Stroll through the Williams College Museum of Art, which houses 14,000 works, including modern and contemporary Chinese art, Indian art and works by iconic American artists Edward Hopper and James Whistler. Don’t miss dinner at Mezze Bistro + Bar, a contemporary American, seasonally focused restaurant nestled in a periwinkle-colored 19th century building.
Where to Stay
Club Members can stay at fantastic Berkshires properties, including Hampton Inn & Suites Berkshires–Lenox and Hilton Garden Inn Lenox/Pittsfield, conveniently located near major attractions.
*The photo featured at the top of this article is of the gardens at Edith Wharton's former home, The Mount. Photo by Kevin Sprague.