Solitude, Steeples and Smart Luxury: An Insider’s Guide to Litchfield County, Connecticut

For years, New Yorkers have quietly slipped into Litchfield County, Connecticut, for weekends away from the city, bypassing the default trio of the Hamptons, Hudson Valley and Catskills. Technically the southern edge of the Berkshires, this northwest corner of Connecticut has a character all its own with historic town greens, working farms reborn as vineyards and winding roads lined with stone walls. The scenery alone could carry the trip, but Litchfield Hills, as the region is sometimes called, has evolved into far more than a postcard backdrop.

Today, the county’s 26 towns balance old New England charm with a sophisticated undercurrent. In Salisbury, Lakeville and Cornwall, farmhouses that look modest from the road conceal carefully restored interiors, while in Washington and Litchfield, discreet weekenders from Manhattan blend into a social scene that still orbits around the local farmers’ market. Fall brings out the best of the area: foliage blazing red and gold, antique fairs popping up in barns and harvest festivals filling the greens.

It’s also a destination that rewards curiosity. Spend the morning hiking the Appalachian Trail near Kent, the afternoon browsing New Preston’s design-forward boutiques, and the evening over a farm-sourced dinner at Community Table. Winter slows the pace but sharpens the experience, with ski jumps that rival Vermont, cross-country trails with smashing vistas, or a fireside drink in a centuries-old inn. Whether it’s a quick reset or a long weekend, Litchfield County delivers an escape that feels both chic and unpretentious. Ahead, a guide to seven essential towns and where to stay, shop and eat in each.