The South Shore’s Nautical Mile boats dozens of great restaurants. Here are our picks for the top 8.

Nearly five years after Superstorm Sandy changed the fortune of every seaside community on the island, the Nautical Mile in Freeport has enjoyed waves of new success stories with revitalized restaurants and an ever-popular social scene to go with its laid-back daytime setting.

Besides old favorites like Otto’s Sea Grill, Bracco’s and Woodcleft Crabshack, more recent additions include Rachel’s Waterside Grill and Nawlins Seafood company, which both bring an updated flair to the mile. Rachel’s serves Nautical eaters a taste of sea-worthy new American food, with dockside seating and the best brunch on the mile. Nawlins goes for a more Cajun approach, with New Orleans’ style flair and fare.

The Woodcleft Crabshack is a long-time favorite for eaters near and far. The steamers are always outstanding, as is the zupa di mare, with shrimp, scallops, calamari, clams and mussels over linguine—ask for a lobster tail on top and the Crabshack will gladly oblige.
As for snacks on the mile, Pip’s Ice Cream Parlour and the new Taco Tuesdays beam with treats great for day or night. Taco Tuesdays is a walk-up window that was once Ralph’s Italian Ices (which has moved down the road), serving an array of tacos, platters and empanadas perfect for a daytime snack or the late-night munchies. Meanwhile, Pip’s serves Hershey’s ice cream—the right way to end a hot day or night on the mile.

The Nautical Mile still exists as two distinct worlds, with an older crowd biking and walking the mile during the day and a younger crowd bar-hopping and dancing through the night. The restaurants on the mile, specifically on Woodcleft Avenue, follow this duality, with some of the seaside-view eateries transforming into thumping dance parties when the sun goes down. This best-of-both worlds atmosphere is what keeps the Nautical Mile alive throughout changing trends and anything else Mother Nature throws at it.

Taco Tuesdays

147 Woodcleft Ave. • 516-632-0091 •

Woodcleft Crabshack

150 Woodcleft Ave. • 516-868-6198 •

River House Grille

195 Woodcleft Ave. • 516-608-5226 •

Pip’s Ice Cream Parlour

250 Woodcleft Ave. • 516-868-7139

Otto’s Sea Grill

271 Woodcleft Ave. • 516-321-0633 •

Rachel’s Waterside Grill

281 Woodcleft Ave. • 516-546-0050 •

Nawlins Seafood Company

301 Woodcleft Ave. • 516-206-8100 •


319 Woodcleft Ave. • 516-378-6575

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