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Restaurant hopping along Freeport's Nautical Mile

Halfway Down in Freeport.

The round plate before me contains something called Japanese tuna nachos — which sounds like the winning answer to a Cards Against Humanity question like, “What’s fun until it gets weird?” — but to my utter surprise they’re delightful. No, it’s not the sort of dish that either the foodies or the Japanese would approve of, but I don’t care. The piled pebbles of tartare and avocado in the center are sweet and astringent, and if the rice-paper chips enwreathing them are far too brittle for the backhoe work of typical tortilla chips, they pair perfectly with ginger aioli. There’s no more perfect appetizer this summer.

Credit for suggesting the inspired snack belongs to Randy, a bartender at Rachel’s Waterside Grill, a dependably yar  establishment on the Nautical Mile in Freeport. If I’d listened to my effete food nerd friends with their condescending disdain for anything nacho-fied, I might never have even heard of Japanese tuna nachos — and if I had, I would have probably kept my distance. But the Nautical Mile is a unique place, and as such one must deploy unique strategies for discovering its glories.

Not nearly so long as a mile, much less a nautical one, the road along Woodcleft Canal — conveniently named Woodcleft Avenue — defies easy description. Once a center of shipbuilding, more recently an eating and entertainment destination, the Nautical Mile has a surreal quality to it.

Home to more than a dozen restaurants and bars, many with live music, it also has several charterboat landings, a couple of fish markets, an open-air church and a psychic or two. At times it resembles nothing so much as a themed section of an amusement park.

On the Mile, though, it’s eating that’s the main attraction, which leads us back to our original conundrum: where to go for the best food. My own solution, imperfect though it may be, was to listen to the Mile itself — the people who pour its drinks and serve its food and stroll its sidewalks in search of amusement.

“Where to next, boss?” says Randy as I pay my bill.

“You tell me.”

Minutes later I’ve transported myself to Otto’s Sea Grill, Randy having heard it’s among the best places on the Mile not named Rachel’s. Tommy the bartender here is a large, fearsome man, and he looks at me a long time, with pity,  mostly after I ask for a menu recommendation.

“The baked clams. Of course,” grunts Tommy. “You get five.”

Otto’s, which dates to 1929, is the oldest restaurant on the Mile, and I am drinking in the scenery, admiring the wood-slatted ceilings and listening to barflies jawing about the Yankees — “You never see them get off the plane in T-shirts, they wear suits, it’s the way they do things” — when I hear the clack of half-shells. The clams are generously stuffed, and there are six, not five.

“They don’t come out of a box,” says Tommy by way of explanation.

I wolf them down quickly — too quickly, because now there is nothing to do but pose another question to Tommy. “If you had to eat anywhere else … ”

“I don’t eat anywhere else,” he interrupts. I flinch when he pivots toward another bartender. “Carrie, where would you eat if you couldn’t eat here?”

She thinks. “I don’t know, Halfway Down?”

A crunchy, thoroughly satisfying soft shell crab sandwich turns out to be the fine recommendation of the server there, a woman whose name is lost to history but whose unusual habit of eating chicken wings off a patron’s plate will live in my mind forever. (Later, I learn the patron is a family member, which only partially defuses my alarm.) Halfway Down is, as the name implies, in the middle of the Mile, a terrific indoor-outdoor complex of umbrellas, patio lights, trucked-in sand, and jokes about Hakuna Ma Vodka meaning no memories for the rest of the night.

There are missteps. Both I and the woman next to me order “tropical” Long Island iced teas. Hers is clear, mine a shade of blue that recalls 2000 Flushes. Neither of us says a word, however, instinctively sensing that only wimps complain at Halfway Down. Besides, this would require that the waitress stop eating wings long enough to hear the complaint, and that is obviously not happening. Only much later do I finally get a Mile recommendation. “River House,” she tells me, pausing to swallow first.

“There’s danger in getting directions from an Irishman,” warns Mickey at River House Grille, by which I think he means the signature paella or plate of crisp fried shrimp squiggled with Russian dressing he had recommended. Nope, he’s stalling to keep from suggesting another restaurant. In fact he never does. During a shift change I watch a condenser drip water from above (“it’s our in-house shower,” Mickey had said), offer my thoughts on Manny Pacquiao’s career to a fellow patron —  all minus-one of them   — and float in an aural universe where Cat Stevens and Supertramp are back atop the charts, and Rikki still can’t lose that number. Sometime after 5 p.m. the bartender after Mickey arrives, and After-Mickey claims to be a fan of the “ale house.” 

On the day I visit, it’s 95 degrees outside and the air conditioning is out at Jeremy’s Ale House. In my delirium, I imagine that the heat has led all the women on the Mile to rise up as one and hang their bras from the ceiling in protest, for which I could hardly blame them — I’d have done the same thing if I’d had one. Eventually I am advised that the bras have been there for years. Strange songs from unknown bands sing from the speakers (“Caamp” by Peach Fuzz?) and my cholesterol campaign continues apace, courtesy of a plate of greasy-delicious fried scallops atop a bed of fries. There’s Frankie shooting the breeze with the guys (topic: omeprazole), there’s a woman with green nails complimenting another woman’s blue nails, there’s the amiable, seen-it-all faces of Greg and Savannah behind the counter. And yes, there’s the patron who pulls you aside and whispers with a conspiratorial wink that Hudson’s is great “for the ladies.”

Over the past few years, a battle has been raging, for some reason, over where the Long Island Iced Tea was invented, here or on a tiny island in the middle of a river in Tennessee, an island called Long. I know, but let’s move on. A bar in the Volunteer State and Hudson’s on the Mile regularly have tea-offs, it turns out, a usually friendly competition that turned ugly this year after the Hudson’s folks lost and then accused their opponents of having rigged the judging panel. One taste is all it takes for me to declare Hudson’s the hands-down winner, if only because an island just four miles long has no business calling itself that. But I am even more enamored by Hudson’s steak tidbits sandwich, in which an enormous thud of meat is tossed with mozzarella and thickly mortared onto two slices of garlic bread. It is the kind of sandwich that makes for a perfect dinner, and then lunch over the next two days.

A bartender named Adilson at Hudson’s recommended EB Elliot’s as a next stop, and there I find that kung pao calamari, once I get past the name, is just this side of wonderful. Even better is an off-menu item called lobster avocado salad, a sort of guacamole for the A-list set. Otherwise, I listen intently as bartender Joel chats with all the ponytailed men of a certain age who have competed in a recent fluke derby. There are a great many of these at Elliot’s on any given day, and it takes a while for him to work his way over. The good news is that once he arrives, Joel doesn’t hesitate. “Nautilus Cafe, for sure.”

Pinballing my way back across Woodcleft Avenue, I roll into the Nautilus Cafe, with its dining room of white tablecloths, crisply folded napkins, blond wood and Scandinavian austerity. It’s the kind of thing you might see on a Viking cruise ship if it were run by actual Vikings.

“What would you like?” asks Matt at the bar. My standard reply, “You tell me,” sets the stage for a bountiful plate of cold lobster, crab and shrimp, wherein shellfish and horseradish create stupendous explosions in the mouth. I revel in the glory of fresh seafood in this refined, retro atmosphere, and hazard a guess that the man two stools down has an opinion about The Incident. He does.

When you hear of its profound and lasting effect on 21st-century Freeport, you might be forgiven for thinking that The Incident refers to superstorm Sandy, but in fact it’s the 2016 appearance by rapper 50 Cent at a club on the Mile. In the annals of mayhem, what happened that evening sounds rather tame: rap star sings karaoke, a few fights break out in the crowd, a minimal amount of property damage occurs. The Nautical rile was considerable, however, at least among business owners, although the whole strip seems wary of disrupting the status quo. The man at the bar offers another example: “I mean, I love the Crab Shack, but …” 

The Woodcleft Crab Shack is indeed a place to love, although one in transition. Last year, in one of those moments that undoubtedly mattered more to Milers than anyone else, ownership of the 40-year-old seafood establishment changed hands for the first time. Early reports are that the quality of the food has not declined, and that the Long Island steamers remain a dependably good deal. My newbie’s ignorance about how to eat steamers notwithstanding — what is that bowl of dirty water for, anyway? — I find the little sand-coated bellies delicious, mineral-rich and possibly more transformative than The Incident. Why this or any restaurant would tune a large TV over its bar to the Food Network is a mystery I have never been able to solve, but I’ve nothing but gratitude for the couple one table over who, upon hearing that someone has just eaten nine different things in nine different restaurants on the Mile, wonder why one of those isn’t …

Tropix on the Mile. Fittingly, the final stop on my journey is the last bar on the strip, where the crowd thins and the Mile dissolves into parking lots and historical markers. The end of the road in more ways than one, Tropix plays host to a signature cocktail frightfully blue and potent, a dance floor with an enormous disco ball that’s poised to do serious damage if it ever comes untethered, live bands that actually call themselves Drop Dead Sexy, guys who actually get offended when friends don’t notice they’ve shaved their mustaches, guys who actually call themselves paisan. In other words: awesome. Both day and night, Tropix feels like a paean to gentle, unpretentious rowdiness, much like the rest of the Mile.

Both change from moment to moment, day to day, and part of the fun comes in never having the same experience twice. Most days, though, it’s a safe bet that you’ll find both as fun, flavorful, and entertaining as I did, even as your own Mileage may vary.

Resturant Information

Rachel’s Waterside Grill, 281 Woodcleft Ave., 516-546-0050, rachelswatersidegrill.com

Otto’s Sea Grill, 271 Woodcleft Ave., 516-378-9480

Halfway Down, 153 Woodcleft Ave., 516-608-0700, halfwaydownthemile.com

River House Grille, 195 Woodcleft Ave., 516-608-5226, riverhousegrillerestaurant.com

Jeremy’s Ale House, 239 Woodcleft Ave., 516-623-0204, jeremysalehouse.com

Hudson’s on the Mile, 340 Woodcleft Ave., 516-442-5569, hudsonsonthemile.net

EB Elliot’s, 23 Woodcleft Ave., 516-378-8776, ebelliots.com

Nautilus Cafe, 46 Woodcleft Ave., 516-379-2566, nautiluscafe.com

Woodcleft Crab Shack, 150 Woodcleft Ave., 516-868-6198, woodcleftcrabshack.com

Tropix on the Mile, 395 Woodcleft Ave., 516-623-8767, tropixonthemile.com

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