Private charter to & from Great Barrington

Great Barrington is the main town of the southern Berkshires, a compact downtown of restored brick buildings, independent shops and restaurants set along the Housatonic River. Much of its economy depends on the second-home owners, weekenders and remote workers who have turned the surrounding countryside into one of the most desirable corners of New England, along with farms, small food producers, real estate and the arts. Bard College at Simon’s Rock and the Mahaiwe Performing Arts Center add a cultural life that lasts well beyond summer.

From New York City the drive takes roughly two and a half to three hours, and from Boston about the same, much of it on two-lane country roads at the end. Flying private into Pittsfield, or another nearby airport, shortens the trip to a fraction of that and lets a Friday-afternoon departure become a Friday dinner in town. Visitors come to hike Monument Mountain and Bash Bish Falls, ski at Butternut and Catamount, browse the antiques shops in Sheffield and spend summer evenings at Tanglewood or Jacob’s Pillow.