George Washington, Amistad — and something called Leisurama. Historically speaking, Montauk has a lot of texture and legend, making its mark in each century of the nation’s history. Montauk Point Light, which stands as a symbol of that legacy, was approved for construction in 1792 under President George Washington; as such, it was the first public works structure built by the new U.S. government (visitors welcome). Nearly 50 years later, slaves who had taken over the Spanish ship La Amistad briefly disembarked near Montauk Point. And in the 1960s, a slew of prefab homes branded Leisurama were plunked down in Montauk to represent the typical American house. These days, people come to Montauk for the same reasons they did midcentury: to kick off their shoes, take to the trails over the grassy dunes, fish either onshore or offshore, and head out on the water on a sailing charter or sunset cruise.

Montauk is synonymous with fishing and sportfishing, and you would be smart to come here to savor the fruits of those labors that end up on your plate. Menu favorites include the local fluke and all manner of tuna poke and tartare (Crow’s Nest features both fish, as well as a Mediterranean-infused menu). Proximity to the coast of Maine means that lobster platters and lobster rolls are ubiquitous, from Duryea’s Lobster Deck and Red Hook Lobster Pound to a place that’s literally called The Lobster Roll Restaurant. At Bird on the Roof, you can shop and eat — the place is as popular for its beachwear as it is for its pancakes. Gosman’s Dock is another excellent place to mix dining and shopping: Have a waterside meal or frozen drink at Gosman’s Seafood Restaurant, Gosman’s Clam Bar, or Gosman’s Topside, then hit Homeport for gifts, accessories, and furniture.