Southern Boating

Where to Eat in Freeport, NY

Devouring the Nautical Mile and all the best places to eat in Freeport.

Find where to eat in Freeport, NY along the best boating community in New York,

A magical tract bordering Freeport’s Woodcleft Canal in New York, the Nautical Mile is the logical starting point for captains and crew visiting this boating-friendly community. Freeport calls itself the “Boating and Fishing Capital of the East.” While that may be a bit of a stretch on both counts, it certainly features a busy, vibrant waterfront with a long history of seafaring tradition that seems to be ever trending toward tourists’ taste-worthy economy. That’s why we’ve rounded out the best places to where to eat in Freeport.

Built upon decades of discarded oyster and clam shells, this is the place Guy Lombardo’s band called home and, in fact, the street paralleling the east side of the canal bears the famous band leader’s name. It’s on Woodcleft Avenue along the west side of Woodcleft Canal, which is also where you can step ashore, stretch your legs and find the ideal place to grab a bite, a drink or both.

Eat, Drink and be Merry

If you’ve brought an appetite, you are certainly in luck, for there are more than a dozen places to dine along the canal itself. Most of the waterfront establishments have transient dockage, and the village of Freeport maintains several slips on a first-come, first-served basis at the Esplanade on Woodcleft Avenue between Suffolk and Hamilton Streets. Use the pay meters along the esplanade to receive the $5.00 per hour tie-up fee and go out to eat in Freeport.

Now, what’s your fancy? Seafood, steaks, ribs? Cajun, Creole, Cuban, Jamaican, Tex Mex? How about a juicy burger or a seat at a Tiki Bar with a big, fruity drink and a colorful umbrella? A raw bar, a crab shack, ice cream, shaved Italian ice? This stretch has them all.

One of my favorites here is E.B. Elliot’s at the head of the canal. Open daily for lunch and dinner, its happy hour runs from noon until 7 PM on weekdays. Here you’ll find great seafood, steaks and the best mojitos north of Cuba, plus live bands on the weekend. Take a seat on the second floor for an entertaining view of maritime mayhem on the canal.

Then there’s Otto’s Sea Grill. Established in 1929, it’s clearly the oldest business on the canal. You’ll find a terrific outdoor raw bar here plus inside dining for seafood, steak, and pasta as well as live music Wednesdays and weekends. Rachel’s Waterside Grill is another great option and known for new American seafood; it serves breakfast, lunch, and dinner. Hudson’s on the Mile offers more traditional seafood, music, a raw bar, and mimosas. For something completely different, Nawlins Seafood Company is the Big Easy of the block. Take your choice of Creole or Cajun cuisine or try the lobster sliders for a deliciously mild treat. Any dish blackened is sure to be a winner. There’s live music here, too.

South Beach + Vegas + Long Island = Tropix

At the opposite end of the spectrum, Tropix on the Mile is where South Beach meets  Vegas—Long Island style. Casually classy, kick up your feet in the sand during the day, strut your stuff to dance music after dark, and wine and dine anytime on flatbreads, burgers, sandwiches, entrees, sushi, salads, or appetizers. Try the buffalo flatbread, Beyond Fitness Turkey Burger, or the watermelon and goat cheese salad. There’s a solid kids menu here as well.

Of course, you’ll want to sample some local wines. Most are produced on Long Island’s North and South Forks, but you can taste them right here. Selections from Pindar, Martha Clara, and Lenz are well worth trying. For a quality wine at a reasonable price, order the 2015 Pindar Sunflower Chardonnay, if available. It pairs especially well with light seafood. Choose the Lenz Gold Label Chardonnay to enhance slightly heavier platters. They’re all terrific choices in their own right and add up to a Nautical Mile of fun.

By Ryan Thomas, Southern Boating June 2018

Photos Courtesy of Hudsons on the Mile, Otto’s Sea Grill and Tropix on the Mile