Montauk

Montauk has made its mark across the centuries. The most literal shining example of that legacy is the Montauk Point Light, constructed in 1796 under the authorization of President George Washington. Therefore, it was the first public works structure built by the then-new U.S. government. For a steal of $2.5 million, entrepreneur Carl G. Fisher bought most of the East End in 1926, intending to make Montauk the northern counterpart to Miami Beach. The 1929 stock market crash scuttled those plans, but not before he erected around 30 Tudor Revival-style buildings. Leisurama arrived in the early 1960s, plunking down 200 prefabricated vacation homes in Culloden Point. Perhaps Montauk’s biggest allure today is its fishing. Whether it’s onshore, aboard a sailing charter, or submerged in the water for skishing, you are bound to find people casting off and setting all kinds of saltwater records.

Waterside eating and drinking options are, in general, abundant. Because Montauk is synonymous with fishing and sport fishing, you’d be wise to savor the fruits of that labor by putting daily catches like fluke and tuna onto your plate. Lobster rolls and platters, along with local oysters from Gardiner's Bay, further anchor the menu of local staples. The area also has its fair share of non-seafood eateries, in addition to bakeries, coffee shops, food markets, and a brewery. Retail isn’t strictly limited to water-wear wares; however, there is a particular focus on stores looking to outfit your next beach or fishing venture. As a summer vacation destination, there are plenty of shops selling the perfect souvenir to commemorate your trip or thank your neighbor for watching the pets back at home.