New Milford: 82 miles NE of New York City; Lake Waramaug: 92 miles NE of New York City; Litchfield: 112 miles NE of New York City; Norfolk: 133 miles NE of New York City and 136 miles SW of Boston
When the Hamptons got too pricey, too visible, and too chichi back in the 1980s, a lot of stockbrokers, CEOs, and celebs started discovering the Litchfield Hills, arguably the most fetchingly rustic yet still sophisticated part of Connecticut.
The topography and, to an extent, the microculture of the region are defined by the river that runs through it, the Housatonic. Broad but not deep enough for vessels larger than canoes, it waters farms and villages and forests along its course, provides opportunities for recreational angling and float trips, and, over the millennia, has helped to shape these foothills, which merge with the Massachusetts Berkshires.
Men in overalls and CAT caps still stand on the porches of general stores, their breath steaming in the bracing autumn air. Churches hold pancake-breakfast fundraisers; neighbors squabble about development. That's one side of these bucolic hills, less than 2 hours from midtown Manhattan.
Increasingly, the other side is fashioned by refugees from New York. These chic seekers of tranquillity and real estate fled to pre-Revolutionary saltboxes and Georgian Colonials on Litchfield's warren of back roads and brought Manhattan-bred expectations with them. Boutiques fragrant with designer coffees and cachets opened in spaces once occupied by luncheonettes and feed stores. Restaurants discovered sushi and sun-dried tomatoes and just how much money they could get away with charging the newcomers.
Compromises and city-country conflicts aside, the Litchfield Hills remain a satisfying all-season destination for day trips and overnights from metropolitan New York and Connecticut.