During the more discriminatory days of the early Twentieth-Century, middle-class Jews often found themselves unwelcome guests at many resorts throughout the United States. As the exhilaration of the “Roaring Twenties” swept the nation, the Jewish community would not be denied their share of the excitement, and the rural solitude of the Southeastern New York seemed to be the perfect elixir.
Before long, the region was transformed into something of an oasis that catered to the ethnic whims of those who had been denied elsewhere. A vast array of indulgent hotels and resorts sprung to life throughout Sullivan, Orange, and Ulster Counties; establishments that played to the wants and needs of their clientele, and in doing so, became the popular vacation spot for Jewish New Yorkers.
By the same token, such celebrity was bound to attract a few figures of questionable notoriety. Quite predictably, it didn't take long for Italian and Jewish mobsters to recognize the upside of sinking their hooks into the sizeable profits to be made in such an atmosphere. Gangsters like Waxey Gordon found the allure of these hotels irresistible and the perfect vehicle for his bootlegging and illegal gambling ambitions. Even so, the next half century was to become a booming time for the Borscht Belt.
During the first half of the century, these popular Catskill destinations could be accessed from New York City by means of a single corridor – New York State Route 17. For those who have never traveled its expanse, Route 17 is a twisting, turning two-lane road that carves its way through the Ramapo Mountains into the more rugged reaches of the Catskills; a snake-like passageway that found its humble beginnings as the main portion of an auto trail known as the Liberty Highway. While today, it is a sleepy byway that is traversed by sightseers who may enjoy taking in the nostalgic charm of its meandering design on a Sunday afternoon, a half century ago it was by no means a joyride.
During the Summer of 1930, a 36-year-old Russian immigrant named Reuben Freed traveled the very same stretch of Route 17 described above towards the small hamlet of Southfields. His mission was to meet a gentleman named Anton Thomas with the intent to pick up some automotive parts. When Freed arrived at Thomas' home along Route 17, the two struck up a conversation. Thomas, who made his living directly across the street at a refreshment stand with a single gas pump, mentioned in passing his desire to sell his stake in the business and see his humble operation turned into a full-fledged restaurant and gas station. This seemingly innocuous statement struck a chord with Freed.
Freed was an enterprising individual who had already dabbled with some success in the garment industry. He took note of the location and its close proximity to the highly-traveled route for vacationers. Taking a moment to consider the fact that the soon-to-be-opened George Washington Bridge would only serve to increase traffic, he flirted with the idea that "just maybe" he could make this work. Clinging to that belief and without a lick of food industry experience, Reuben Freed borrowed $1000.00 from the Tuxedo National Bank to purchase the restaurant equipment he would need, and on Memorial Day weekend of 1931, he opened the Red Apple Rest.
Located just under 50 miles from New York City and closer to 60 miles to the Catskill Mountains, the Red Apple Rest resided at the approximate midway point for travelers making their way to and from the aforementioned resorts. Freed recognized the value of this location and marketed his restaurant by strategically placing a dozen or so billboards along the Route 17 corridor announcing how many miles were remained until one arrived at the Red Apple Rest. Today, many remember their childhoods in the back of the family station wagon excitedly counting down the distance with each passing marker - "RED APPLE REST - 25 MILES! RED APPLE REST - 20 MILES! RED APPLE REST - 10 MILES!" and so on.
What had began as a mere roadside convenience – a mid-trip pause for refreshments, rest, and fuel – soon evolved into tradition. Families could no longer pass the establishment without pulling in. It became a prerequisite stop for any passerby. And middle-class vacationers and travelers weren't the only ones enamored with the Red Apple Rest.
Many celebrities also made the Red Apple Rest a regular stop on their jaunts to their bookings in the Catskills. In fact, it wasn't all that unusual to see Milton Berle milling about and cracking a joke while ordering a meal.
In his book, The Haunted Smile, author Lawrence J. Epstein would relate how Jewish comedians would stop in during the wee hours and "go over the acts,” and "gather gossip about the other comedians and about routines ripe for buying or 'borrowing.'" Even George Carlin, who would stay in Room 102 of the Red Apple Motel directly across the street, was known to run some of his new material past the night shift desk clerk and then venture in for a quick bite.
The restaurant was more popular than Freed ever imagined it would be. During the 1950's, the Red Apple Rest served over a million customers per year. It's spacious, 300-car parking lot would be filled with a myriad of vehicles - station wagons with valises lashed to their roofs, Airstream campers hitched to stylish sedans, and a fleets of buses filled with rambunctious, camp-destined children. So many, in fact, the restaurant needed to dish up over 350,000 hot dogs per year to feed this hungry bunch. But even in light of such success, by the late Fifties, the restaurant was about to begin a steady decline in fortunes.
Although this new, multi-lane highway bypassed the Red Apple Rest completely, it didn't have a huge effect on business - at least at first. There were still hordes of loyal travelers determined to make a stop at their favorite place for refreshments. Although the restaurant's popularity had somewhat tailed off since their halcyon days a decade earlier, it still did a bustling business throughout the 1960's. But with the onset of the Seventies, the economic downturn brought about by the changing times became harder and harder to ignore.
The Thruway now had its own rest areas; all shinier, newer and more conveniently located than the Red Apple Rest. The Catskill's hotels and resorts - once so wildly popular - were also experiencing a steady decline into obscurity. Lower fares made air travel more affordable and vacationers began venturing farther and farther from home. Competition from places like Busch Gardens, Disney World and Las Vegas - as well as a budding seaside industry along the Jersey shore - suddenly vied for the same dollar as the Borscht Belt. To further exacerbate the foundering resorts' struggles, the advent of gambling in Atlantic City all but sealed their fate. One by one, they began to close down and fall into ruin.
The writing was indeed on the proverbial wall. Freed's roadside eatery simply could not keep pace with the changing times and its new status as little more than a relic from a bygone age was all too obvious. Even so, Reuben Freed was still entirely committed to the Red Apple Rest at the time of his passing in 1980. The family held on another four years, until Herbert Freed finally relinquished his father's dream and sold business to Peter Kourakos in 1985.
To his credit, Kourakos managed to keep the Red Apple Rest alive and functioning until September 2006, at which time, a cryptic sign appeared on the door stating the restaurant was “Closed for graduation and vacation.” It would never reopen.
The building was condemned on January 23, 2007 because of roof damage. Many of the windows were boarded up and the building quickly fell into disrepair. As the years rolled by, one was still able to peer inside and look upon the eerie interior that seemed untouched by time. Tables and chairs sat where they had always been, seemingly waiting to be filled by yet another busload of customers. In the musty shadows stood an old phone booth with a non-existent dial tone. Pictures and maps still hung upon the walls, while a counter gathered dust as if awaiting one last one-liner from Milton Berle.