Sag Harbor

A prosperous deepwater shipping port on the south shore of Long Island, Sag Harbor was in its heyday as a whaling village in the early 1800s. By 1850, whaling was unprofitable, petroleum had been discovered, and the 1849 Gold Rush led to an exodus. As Sag Harbor fell into economic decline, the arrival of the railroad helped reinvigorate it as a factory town, bringing Fahys Watchcase, Alvin Silver, Bliss torpedo testing, and Bulova, until those industries shuttered. The silver lining to Sag Harbor's boom and bust has been the preservation of its heritage. The grand homes of captains and whaleship owners, tradesmen's cottages, and factory houses were untouched for years, attracting a wave of artists, writers, and weekenders. This fine collection of 18th- and 19th-century homes and public buildings placed the village in the National Register of Historic Places, drawing tourists to walk in the footsteps of Native Americans, colonists, whalers, and resident-writers James Fenimore Cooper and John Steinbeck and to visit the village's war monuments and museums and charming Main Street.