by Len Boccassini
It was a simpler time; an age when strains of laughter could be heard ringing throughout the wooded hills of New York's Catskill Mountains and the region buzzed with activity. Within the scores of hotels and resorts that made up what was colloquially referred to as the “Borscht Belt”, mostly-Jewish audiences were treated to a host of comedians and entertainers that included everyone from Milton Berle and Don Rickles to Mel Tormé and Benny Goodman. In other words, anyone who was anyone performed at these venues that became a proving ground for stars to be, and a destination for those already established. During its heyday, playing the Catskills meant playing the "Big Time". But it wasn't always that way.
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.
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.

Establishments like Grossinger's, Brown's, The Nevele, The Concord, and the Tamarack Lodge soon became household names, and with that flourishing renown, they easily attracted nationally-recognized acts to entertain their guests. In fact, it's safe to say that nearly every noteworthy Jewish comedian of the Twentieth-Century would eventually come to perform at one of these venues.
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.
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.
The route, was often found to be pitted and pock-marked as a result of the harsh New York winters. Driving conditions along its twisting, unlit conveyance could often be hazardous, particularly at night or during inclement weather. During the best of times, it could be a four or five hour ride from the city to any of these Catskill destinations, but during the busy summer season, congestion could slow traffic to an agonizingly crawl and stretch travel time considerably.
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.
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.

As the story is often told, Freed named his new establishment after his cook, Red Appel; a moniker gained due to his shock of rust-colored hair. Reuben Freed was a slightly-built and congenial man who had an immense work ethic few could approach. Insisting on working in a suit and tie, he immersed himself in his establishment 24 hours a day, 7 days a week. The new restaurateur refrained from ever locking the doors of his Red Apple Rest, even on holidays. For Freed, it was business as usual, 365 days a year.
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.
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.

The first blow to strike the eatery occurred in 1953 with the completion of the New York State Thruway. Four years later, a new artery branched off from the Thruway and made its way into the Catskills, a more direct stretch of Route 17 referred to as the "Quickway". This newer route, cut travel time nearly in half and deemed its older counterpart - the bumpy, winding road that passed through Southfields - virtually obsolete.
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.
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.
This downturn in business was a direct result of the many circumstances that were quickly bringing change to the everyday fabric of life in the latter half of the 20th-Century:
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.
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.
Kourakos, a 52-year old Greek immigrant, ran the business with his wife, his daughter and a staff of three; quite a drop-off in personnel from the restaurant's glory days. Kourakos managed to eke out a living with his small staff by putting in 15-hour days and seven-day weeks, and the modest business he did do, was mainly a weekend biker crowd that made the Red Apple Rest a rallying point. It is sufficient to say, to continue on in such a manner was not conducive to any long-term means of success.
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.
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.
Today, at the time of this writing, the structure still remains. It takes but a single glance to recognize it is quite dilapidated, and obviously, in very dangerous state. It is surrounded by a fence to keep those in search of nostalgia at bay, and is a piece of regional history I cannot envision surviving much longer. I am an avid admirer of yesteryear and I am certain before long, all indications of the Red Apple Rest's very existence will be eradicated from this earth once and for all; replaced by a shiny, new chain eatery, or perhaps, yet another half-occupied strip mall. For me, that is a heartbreaking reality. Yet another casualty to our collective youth in the name of progress.