By Shaun Tolson
This story originally appeared in the July/August 2018 issue ofElite Traveler.
Since the mid-19th century, when train service first connected Boston to the upper region of the hook-shaped peninsula that is Cape Cod, New England’s wealthy elite have summered here. Former President Grover Cleveland built the Cape’s first ‘summer White House’ during the 1890s, and the Kennedys began vacationing in the village of Hyannis Port only a few decades later. Spanning 339 square miles with more than 500 miles of sandy beaches, the Cape acts as a barrier island to a large swath of Massachusetts shore; but unlike a traditional island, which typically fosters a single dominant culture and lifestyle, Cape Cod is a patchwork of four distinct regions. The historic Upper Cape is home to loads of charming museums and a popular ferry connection to Martha’s Vineyard. The Mid-Cape is diverse and densely populated by miniature golf and ice cream establishments, but is also rife with tranquil ports and harbors. The Lower Cape, elegant and picturesque, is best known for its luxurious resorts, quaint towns and exclusive golf clubs. And the Outer Cape, with its national-park-protected seashore, is wild and windswept but also refined, thanks to the cosmopolitan culture of its largest town, Provincetown. Simply put, Cape Cod offers something for everyone.