North of Manhattan Beach and south of everything else in Brooklyn, this waterfront district is brimming with old-school Brooklyn character. Sheepshead Bay is named for a striped fish species that was once catchable in the adjacent bay, but these days is found in more southerly waters. The neighborhood once boasted a race track—originally for horses and later for automobiles—that shuttered in the early 20th century.
A walk down Emmons Avenue, which runs along the bay, shows that the area’s seafaring roots run deep. The docks are bristling with fishing boats with names like the Atlantis and Lady Midnight, from big ones that you can charter for the day to smaller private crafts. If you fancy an afternoon on the waves, book a half-day on the Sea Queen VII, which embarks on three trips a day. Tickets are $35 to $45, and you can rent a rod ($5) to catch your own sea bass, porgies and flukes.
Fill up after your trip at Roll-N-Roaster, a 43-year-old burger joint that will make you feel like you’ve time-warped back to the early 1970s. Order one of the spot’s signature roast beef sandwiches from the uniformed waitresses and cozy up to an old-timey booth. If you’re a fan of the yellow stuff, you’re in luck: A sign behind the counter promises that “You can have cheez on anything you pleez.”
If it’s a nice day, stroll across the recently restored 19th-century footbridge that spans the bay from Emmons Avenue to Shore Boulevard in adjacent Manhattan Beach. Walk through the upscale residential neighborhood to reach the beach itself, which is surrounded by parkland and is less crowded than the shoreline in Coney Island and Brighton Beach to the west.
Sheepshead Bay has its share of hometown heroes—comedian Larry David and actress Michelle Trachtenberg both grew up here—but the ’hood’s most famous former resident is NFL legend Vince Lombardi. The house where the Packers coach grew up still stands at 2542 East 14th Street, only a block away from the Sheepshead Bay subway station. There’s no grand statue, but you can snap a photo of a memorial plaque honoring the man in a traffic triangle at the corner of East 17th Street and Jerome Avenue.
For dinner, head to Maria Ristorante, a neighborhood fixture for more than 70 years. The atmosphere is vintage Italian-American Brooklyn, and the portions are generous. Since you’re by the water, try seafood dishes like shrimp fra diavolo and broiled lobster tail.
Wrap up the night with dessert at Masal Cafe, a Turkish spot with outdoor seating across from the bay. Order confections like the Napoleon, layered with pastry and custard and drizzled with caramel, or a Turkish waffle topped with gelato and fresh fruit. Before you hop back on the subway, be sure to take a photo in the head-in-the-hole ocean scene on the station wall.