Long Island’s South Shore and North Shore offer vastly different scenery. The coastline of the South Shore beckons with its powdery white sands, bustling Nautical Mile, and venerable Montauk Point Lighthouse. The North Shore, with its majestic rocky bluffs, regal Gold Coast mansions, and easy charm of places like Greenport Village, calls to swimmers, surfers, sailors, and sunbathers. Inland you’ll find an agricultural treasurehouse, nurturing vineyards to rival their Californian and European counterparts and food producers catering to the farm-to-table ethic of many of the region’s restaurants.

This is an area with a long and fascinating history. Before being settled by Europeans in the 17th century, the island was occupied by 13 Native American tribes with names that may sound quite familiar: Rockaway, Merric, Montauk, and Manhasset. Agriculture was the basis of its early economy, and later in the 18th and early 19th centuries, whaling brought a period of wealth and prominence. In the years following the Civil War, well-to-do Americans discovered the pleasures of saltwater bathing and sea breezes, and the farming and fishing communities of the Hamptons were slowly transformed into fashionable summer resorts. The North Shore became the playground of the Vanderbilts, Whitneys, and Roosevelts. After World War II Americans began owning automobiles, highways were constructed, and the middle class moved out to Long Island, converting farm fields into suburbs.

Long Island does not stand still (though the same might not be said of its roads on a peak-season weekend), but beyond the hubbub of traffic and a sprawl of new homes and commercial districts, old village centers with historic sites and museums preserve the island’s rich heritage, and parks, golf courses, nature preserves, and those glorious beaches provide the space to reflect and breathe in the fresh sea air.