Red Apple Rest in Tuxedo, NY (permanently closed)

Perched on the sun-baked shoulder of New York State Route 17 in the hamlet of Southfields, Tuxedo—48 miles north of the George Washington Bridge and a tantalizing 60 miles shy of the Catskills' bungalow colonies—the Red Apple Rest loomed like a promise of respite for weary travelers. Opened on May 1, 1931, by Russian Jewish immigrant Reuben Freed with a modest $1,000 bank loan and a $3,000 outlay for silverware, this sprawling cafeteria-style eatery quickly blossomed into the Borscht Belt's unofficial gateway. Crowned by a massive, apple-shaped sign that glowed red against the dusk, it was no mere diner but a cultural crossroads: a 24/7 haven open 365 days a year, where the aroma of sizzling hamburgers mingled with the chatter of aspiring entertainers en route to summer gigs at Grossinger's or the Concord. For Freed, inspired by a cousin's delivery run to a dusty gas station on that very stretch, the Red Apple was a gamble that paid off in spades—nearly a million patrons by 1965 alone, including busloads of families fleeing Gotham's swelter for mountain air and mah-jongg marathons.

The 1940s and '50s were its fever-dream zenith, a postwar paradise amid Route 17's bumper-to-bumper exodus. Picture the scene: chrome counters lined with swivel stools, where comedians like Sid Caesar or Jerry Lewis nursed black coffee between one-liners, scribbling jokes on napkins over plates of fluffy pancakes drowned in Log Cabin syrup or juicy Reubens piled high with sauerkraut. The menu was a democratic feast—hamburgers for a quarter, turkey clubs for under a dollar, endless refills of Sanka—serving not just vacationers but locals from Tuxedo's quarries and the nearby Ford plant in Mahwah. Billboards heralded its approach for miles: "Seven miles to Red Apple," "Four miles," down to "500 feet," building anticipation like a striptease. Even the 1953 opening of the New York State Thruway, which siphoned speedier souls northward, couldn't dim its allure; Freed's daughters recall Sundays swelling to 20,000 souls, the open-air counter in summer buzzing with Catskills-bound buses, the jukebox crooning Yiddish folk tunes amid the clatter of trays. It was more than meals—a social salve for a transient tide, fostering chance encounters that birthed lifelong bonds and, legend has it, a few showbiz sparks.

Hollywood couldn't resist: Woody Allen's Deconstructing Harry (1997) captured its faded patina, with Dustin Hoffman nursing a malt amid the Formica glow; it popped up in A Walk on the Moon (1999), Tenderness (2008), and even Oliver's Story (1978), its neon a shorthand for nostalgic Americana. Bill Griffith's Zippy comic strip immortalized it in 2013, a quirky eulogy to its quirky charm. Yet, by the 1970s, the magic curdled. The Catskills' decline—air travel to Florida, Disneyland's siren call, and the Thruway's bypass—eviscerated traffic. Freed sold after 53 years in 1984 to Greek businessman Peter Kourakos, who limped it along as a quiet local haunt until September 2006, when it shuttered abruptly with a cryptic sign: "Went away for a graduation and vacation." Condemned in 2007 for a caving roof and peeling paint, it decayed into an eyesore—its iconic apple crashing through the ceiling in the early 2010s, vines clawing at shattered windows—while listed vainly at $2.2 million, eyed briefly for a British Ace Cafe revival that fizzled.

Demolition in November 2023 sealed its fate: a third of the structure bulldozed voluntarily by the owner, the rest structurally sound but adrift on its 3.2-acre lot, zoned for anything from a car wash to a bowling alley. Social media erupted in grief—Reddit threads and Facebook posts from the Tuxedo Historical Society brim with foliage-ride memories, first-date fries, and pleas for rebirth amid Resorts World Catskills' shadow. Elaine Freed Lindenblatt's 2014 memoir Stop at the Red Apple (SUNY Press) distills the ache, chronicling 50-plus years of family grit and fleeting glory. Economically, it anchored Tuxedo's tourism, employing generations; culturally, it bridged immigrant hustle to pop pantheon.

In Route 17's relentless churn—from Orseck's rivals to Shorty's ghosts—the Red Apple's closure whispers of impermanence: a balm for nostalgia's cortisol dip, per studies, turning spectral sips into shared reverie. As excavators idle, perhaps a plaque or pop-up honors its apple core—proof that some rests refresh the soul long after last call.

https://skywaydiner.com/product/23794595/red-apple-rest-tuxedo-ny-tribute-mug