Towards the east-pointing tip of Long Island's South Fork, you'll find the mellow town of Montauk, aka 'The End,' and the famous surfing beach Ditch Plains. With the surfers have come affluent hipsters and boho-chic hotels, but the area is still far less of a scene than the Hamptons, with proudly blue-collar residents and casual seafood restaurants.
Route 27, the Montauk Hwy, divides east of Napeague State Park, with the Montauk Hwy continuing down the center of the peninsula while Old Montauk Hwy hugs the water. The roads converge at the edge of central Montauk and Fort Pond, a small lake. Two miles east is a large inlet called Lake Montauk, with marinas strung along its shore.