I’ve always loved fresh seafood since I was a kid, when my father brought me on charter fishing boats to catch porgies on the Long Island Sound. Over the years, my penchant for fish evolved into a full-blown love affair with all types of seafood, from grilled octopus to oysters on the half shell. So when I heard about Freeport, the Long Island port town where fishing boats haul in fresh seafood to serve in the local restaurants, I knew I had to visit. 

My gastronomic journey, shared with my friend and her kids, began at noon in this southern shore town, a 48-minute LIRR train ride from Penn Station.

From Freeport station, it’s a short ride to “The Nautical Mile,” a bustling strip of bars, seafood outposts, and boutiques along Woodcleft Canal. 

Dredged in the late 19th century, Woodcleft Canal was once the center of the largest waterfront main streets on Long Island’s south shore. Boats were built here for American and British navies during World War II, but the area morphed into a marina for recreational boats and charter fishing vessels. With that came fish markets, world-class restaurants, and no shortage of raucous bars. Today, you can even take jet ski tours of the southern coastline nearby.

With Freeport’s longtime maritime history, it’s no surprise oysters are part of the allure. Several restaurants serve raw oysters on the half shell, especially local (and easily) sourced Blue Points, named for the south shore town of Blue Point. These tasty mollusks are known to be mild, yet briny. However, that’s just a textbook flavor profile description, and palates vary—especially for children.

“I like how it was sweet and had just a little spice to it,” said Cailin, my friend’s culinarily curious eight-year-old, upon slurping down an ungarnished Blue Point. We were at the Nautilus Café, an elegant restaurant acclaimed across Long Island for its fresh seafood and courteous service.

After this first stop on our self-guided oyster crawl, we continued down the Nautical Mile, strolling past fishing boats poised to bring fishermen out to sea and floating booze cruises. Psychics offered impromptu readings to the curious while families hit balls at the miniature golf course across the street. 

We tried more Blue Points, chilled on the half shell, at Otto’s Sea Grill, a seafood joint with a kitschy tiki bar vibe.

“On a scale of one to 10, how yummy was it?” I asked Cailin.

“Eight or nine.” 

Her five-year-old brother, Cole, showed no interest. “Oyster moyster,” he babbled.

Eventually we wound up at the oyster place to visit, according to locals who dig its lively summer party vibe: Bracco’s Clam and Oyster Bar, near the end of Woodcleft Avenue, where “oyster” is in its name. Proudly displaying American, Croatian, and Italian flags waving softly in the ocean breeze, Bracco’s was in party mode that warm Sunday afternoon. 

People sipped drinks on the outdoor bar and dined on the wooden decks. Families gathered in cabanas of Bracco’s faux beach, adorned with palm trees and two plastic sharks. Private boats pulled up for takeaway and to catch some live music by Rasta rockers.

Owner Jerry Bracco invited us in, explaining the motive behind his three flags: His father, Captain Ben Bracco, emigrated from the Italian port town of Trieste on the Adriatic Sea, near the border of Croatia—motherland of many Long Island fishermen. Today Ben Bracco is the namesake of the adjacent Captain Ben’s Fish Market, where the restaurant bearing the family name scores its fresh seafood.

Seated beneath a blue umbrella, my companions and I ordered a feast: Bracco’s Clam Bake, which comprises a gargantuan serving of two whole lobsters, a succulent Alaskan king crab leg, steamed mussels, Little Neck clams, and corn-on-the-cobs, plus a side basket of fried shrimp and fries. Naturally, we requested a dozen raw oysters to start.

“We like the clean, cold water,” said Jerry, noting that, unlike other establishments, his oysters come from Nantucket. “We have the best.”

Cailin’s take: “It was warm and had sweetness to it. I like it more sweet.”

“On a scale of one to 10, what would you give it?” I asked.

“Nine,” she replied.

Better than Blue Points, but only by a thin margin. What would constitute a 10? For me, a West Coast Kumamoto. For Cailin, that was to be determined, but she does have a lifetime to refine her palate, after all. 

Where to get your seafood fix on Nautical Mile

Hibiscus at Elliot’s. Slurp locally caught raw oysters and clams at this lively watering hole. Sure, you could order Jamaican jerk chicken, but why skip fresh seafood standouts, like Mexican fish tacos and spicy Kung Pao calamari? 

Tropix on the Bayou. Now under the same management as the beloved Tropix on the Mile, this restaurant with the cool French Quarter decor deftly mixes Caribbean and Cajun cultures. Here, frozen piña coladas share the table with fresh seafood dishes like Cajun catfish, blackened scallops, and shrimp gumbo. 

Rachel’s Waterside Grill. This elegant waterfront restaurant has served fresh seafood for close to two decades, highlighting all things local on its mouthwatering menu. Options include a Long Island flounder stuffed with blue crab and a broiled seafood platter with Montauk scallops and Little Neck clams.

Erik Trinidad is a freelance food and travel writer/video producer whose work has appeared in Lonely Planet, National Geographic, Fodor's Travel, Wine Enthusiast, and AFAR.