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Boxcar Burgers
Boxcar Burgers opened in January 2020 on Railroad Avenue near the Ronkonkoma train station, founded by Steve Cannon and Mike Dorian — Port Jefferson Station natives who've been best friends since they were 12 years old, and who between them have worked nearly every job the restaurant business offers, from dishwasher up through executive management. They built the concept specifically around Long Island's railroad heritage, working the theme into everything from the name itself to the interior design, under a tagline that sums up the whole pitch: "food that's off the rails." The timing turned out to be almost comically bad and then, eventually, good anyway. Cannon and Dorian designed Boxcar Burgers to catch the daily wave of commuters heading to and from the Ronkonkoma LIRR station — a captive, high-volume audience passing the door twice a day. Then the COVID-19 pandemic hit within weeks of opening and emptied the commuter trains entirely, forcing the two founders to rebuild their customer base almost from scratch around local diners rather than the transit crowd they'd planned for. That the burger joint not only survived that mistimed launch but expanded to three locations, including a spot in the Smith Haven Mall food court, says something about the underlying product. The kitchen leans into quality, freshly baked bread and thick, well-seared patties rather than trying to out-gimmick the competition, positioning itself as a straightforward, ingredient-forward burger built by two self-described "working-class guys" rather than a chef-driven concept chasing culinary spectacle. The railroad framing isn't just a name slapped on a generic burger menu, either — Cannon and Dorian have said explicitly that they wanted to highlight Long Island's rail history in every detail of the restaurant, from the Railroad Avenue location itself to the boxcar-referencing branding throughout. That kind of specific, place-rooted theming is harder to find among the Island's newer burger openings, many of which lean on more generic "gourmet burger bar" branding that could be transplanted to any suburb in the country. Boxcar Burgers, by contrast, could really only exist in a Long Island train town. The Smith Haven Mall food court expansion is a particularly telling data point, since food-court operators are typically choosy about which independent concepts they'll bring in alongside established national chains — landing that slot suggests Boxcar Burgers had built enough of a track record at its original Ronkonkoma location to be treated as a proven concept rather than a risky local experiment, only a few years removed from a launch that could easily have sunk the whole idea. For a Long Island cheeseburger list, Boxcar Burgers is the essential "built around Long Island's own railroad history" entry — a thick, quality-driven patty served a few steps from the Ronkonkoma LIRR platform, founded by two lifelong friends who opened three weeks before a pandemic emptied their target audience and rebuilt anyway.
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All American Hamburger Drive-In
All American Hamburger Drive-In has been flipping burgers on Merrick Road in Massapequa since 1963, and the family that runs it has resisted the urge to change much of anything in the six decades since. There's no indoor seating — just a walk-up window, a handful of picnic tables out front, and a neon sign that's been drawing cars off Merrick Road since the Kennedy administration. It's the kind of drive-in most of the Island's other burger spots are, whether they admit it or not, quietly trying to imitate. The menu is deliberately short: hamburgers, cheeseburgers, and quarter pounders, each available with or without cheese, plus the option to double up into what the menu calls a Double Header or a Double Double. Add a hot dog, onion rings, or a grilled cheese and you've covered the entire board. The patties are thin, griddled hot and fast rather than built up gourmet-style, and the fries are peeled fresh on site rather than dropped frozen from a bag — a detail regulars notice even if they can't always articulate why the fries taste different from everywhere else on the Island. That stripped-down format is the whole point. All American isn't chasing a smash-burger trend or a truffle-aioli upgrade; it's running the same order-at-the-window, eat-at-a-picnic-table format it opened with in 1963, back when drive-ins like this one were common across Long Island rather than a novelty. Writers covering the place consistently reach for the same comparison — a genuine "Happy Days"-era throwback — because it's one of the only spots left on the Island where that description isn't an exaggeration. The restaurant has stayed a Massapequa fixture precisely because it never tried to become anything else. ABC7 New York profiled the drive-in specifically for having "been flipping burgers since 1963," treating the shop's longevity itself as the news. Roadfood.com and independent burger writers, including critic Nick Solares, have separately singled it out as one of the more honest examples of old-school Long Island drive-in cooking still operating, a distinction that matters in a region where most similar spots from that era have long since closed or been remodeled into something glossier. Generations of the same Massapequa families have grown up stopping there, which is part of why the restaurant's Yelp and Tripadvisor pages are stacked with reviewers recalling specific childhood memories of the place rather than just rating the food. For a Long Island cheeseburger list, All American Hamburger Drive-In is the essential "this is what a Long Island drive-in actually looked like" entry — a thin, fast-griddled patty served at a walk-up window with fresh-cut fries, in a Massapequa parking lot that's looked and operated essentially the same way since 1963.
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