Mid-Century Modern Elegance: The Skyline Restaurant and Terrace Lounge, Catskill, NY

by G. Jack Urso

The Skyline Restaurant and Terrace Lounge in the 1960s.

In late 1989, I started a job in education at Hudson Correctional Facility in upstate New York. I spent most days going back and forth over the Rip Van Winkle Bridge in Catskill, NY, connecting the East and West sides of the banks of the Hudson River, not far from artist Fredrick Church’s historic Olana estate. As I crossed over from Hudson to Catskill, just past the toll booths on the right was a turn off with small hill on top of which sat a beautiful 1960s-era Mid-Century Modern building with a large sign that advertised the “Skyline Restaurant.”

Clearly abandoned, the building sat windswept and neglected amid the encroaching scrubs and trees. After a stressful day in the prison, and having a somewhat sentimental nature, I looked forward to crossing the Rip Van Winkle and even getting stuck on it during the seemingly endless construction on the bridge that took place in the early 1990s. It gave me just that much longer to check out the Skyline and marvel at its huge glass windows and slanted wooden beams that had the catbird seat looking over the Hudson. Past the bridge on the opposite side, one could see the large gothic Olana mansion set amid a sculpted landscape. At twilight, the golden glow of the setting sun would bath the Skyline. The scene must have been gorgeous any time of year, but particularly in the fall when an Oriental carpet of colors laid throughout the Hudson River Valley.

The main dining room at The Skyline Restaurant and Terrace Lounge.

Its full name, I discovered many years later, was the Skyline Restaurant and Terrace Lodge. The “Terrace Lodge” moniker recalls the famous Borscht Belt Catskill resort Grossinger’s Terrace Room and, indeed, the name is still used with some finer restaurants to evoke a sense of class and fine dining.

Eventually, my work shifted me north and away from the Catskill area. Many years later, when I returned to teach in prisons, I began crossing the Rip Van Winkle Bridge once again. To my disappointment, the Skyline Restaurant building was gone and if there were any remains, they lay hidden by a thick growth of brush and trees that now obscured the hill.

Overhead map of the north side of the Rip Van Winkle Bridge with the approximate location in red of where the Skyline Restaurant and Terrace Lounge once stood (Google Maps, 2025).

In the decades following my first encounter with the Skyline, I obviously didn’t forget about it, but occasional internet searches revealed little until finally not long ago I came across a post on Facebook in which former customers recalled the old restaurant. Then, I finally had enough information to begin pulling together some history of the restaurant and what became of it. As the Mid-Century Modern design of the building suggests, the Skyline Restaurant was built to cater to that generation and it did so with a classic, and expensive, Mid-Century American menu. 

The Skyline Building

The ten specially laminated wood beams that support the roof each weigh a ton and are 61 feet long, varying in thickness from 6 to 20 inches. The wide fireplace and chimney with its unusual hood are field stone. Floors are Vermont slate, tile and carpeting.

     —     Description from the back of a Skyline Restaurant and Lounge menu.

The main dining room at The Skyline Restaurant and Terrace Lounge, 

looking west out the windows.

The Skyline Restaurant and Terrace Lodge was built and run by Ben and Helen Winter. According to a relative I connected with on Facebook, they operated it throughout the 1960s and later sold it in the early 1970’s. It’s not clear how long it ran under the new owners, but it was definitely an abandoned building by the late 1980s. I suspect it closed down sometime in the 1970s for reasons I’ll get into later.

Looking at the long row of floor-to-ceiling windows and the skylights, anyone who ever had to pay a utility bill probably can see one of the largest expenses likely was the power bill. Sitting on a wind-swept hill above the Hudson River, freezing in the winters, baking in the summers, and not to mention two large walk-in coolers, the electricity expenses must have been considerable. The Winter’s sold it around the time of the 1973 Oil Crisis set in and they were probably lucky to do so. Given the Skyline’s location and reputation, it must have seemed like a wise investment at the time, but one can’t predict how quickly things can change. That is just speculation. There can be many reasons for a business to close completely unrelated to its expenses or income.

Back cover of the menu for The Skyline Restaurant and Terrace Lounge menu, 

circa mid-1960s.

At some point, the structure is reported to have burned down, but exactly when is not known. In the late 1980s and early 1990s, as best as I could tell at the time, the structure just looked abandoned, not gutted by fire, but I could only see the front of the building as I drove by and it sat on a hill a few hundred feet from the bridge turn off. Nevertheless, there may have been a fire and the structure left standing in the hope it could be restored, but a photo posted in 2023 on a Catskill, NY, community group page on Facebook, clearly shows a dilapidated building with the roof fallen in. The photo’s date is not known, and likely before 2023. So, while the date and extent of damage of the fire is unknown, whenever the building was eventually demolished it was after the mid-1990s.

The ruins of the Skyline Restaurant before demolition.
Credit: Clifford Beele, Facebook, Jul. 22, 2023.

What’s on the Menu

Kitchen walls of glazed ceramic tiles, stainless steel equipment, and minimum 180 degree automatic dishwashing . . . Ample refrigeration is provided by two large walk-in coolers . . . our Neptune Live Lobster Tank with its constantly circulating salt water, the next best thing to a lobster’s natural environment . . . keeps them very much alive.

    —     Description from the back of a Skyline Restaurant and Lounge menu.

The Skyline Restaurant and Terrace Lounge menu, circa mid-1960s.

The Skyline’s menu is a model of Mid-Century American dining. If you were a vegetarian your choices were limited to five salads, potatoes, the “vegetable of the day,” and that’s pretty much it. The surf and turf offerings, however, were expansive and expensive. The brief selection below includes both the original menu prices circa 1965 with the 2025 dollar amount in parentheses (according to the Bureau of Labor Statistics CPI Inflation Calculator).

Broiled 16 oz. Sirloin Steak	$5.95 ($61.61)
Broiled 14 oz. Filet Mignon	$5.95 ($61.61)
Spring Lamb Chops	$3.80 ($39.35)
Calf’s Liver	$3.25 ($33.65)
2-lb Lobster	$4.95 ($51.25)
Frog Legs Provencale	$4.00 ($41.42)
Fried Frog Legs	$4.00 ($41.42)
Fried Florida Shrimp	$3.00 ($31.06)
Broiled Brook Trout Amondine	$3.00 ($31.06)
Broiled Swordfish Steak	$2.75 ($28.47)

As you can see, some of those 2025 price equivalents are breathtaking, to say the least. Similar steak dishes are cheaper today at a place like The Outback, but the scope and quality of the Skyline’s menu would be hard to match.

As wide as the menu’s offering are, keep in mind, they had to have all this on hand and be confident they could sell most of it before the sell-by dates.

Inside the menu of The Skyline Restaurant and Terrace Lounge menu, circa mid-1960s.

Another aspect of Skyline’s menu was the wide choice of alcohol, including (among many, many, others) burgundy, champagne, chianti, Rhine wines, sherry, vermouth, port, gin, Courvoisier, Dubonnet, brandy, vodka, and, yes, domestic and imported beers.

The bar at The Skyline Restaurant and Terrace Lounge.

People came to the Skyline to eat the finest cuisine, drink the finest wine and liquors, and pay damn well for it and the service. By all accounts, under the Winter’s ownership, the Skyline did just that.

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Sidebars and Salad Bars

Valle's Steak House sign, Albany, NY, circa 1960s. Credit: Saxon Sign.

The Skyline Restaurant recalls another Mid-Century eatery, Valle’s Steakhouse. A chain scattered throughout the Eastern United States, Valle’s sported a menu of pricey steak and seafood options as well as a cocktail lounge. Several locations, like the one in Albany, NY, and Springfield, MA, sported a Mid-Century building design with fieldstone, timber, and large glass elements. Valle’s got hit during the economic downturn and energy crisis of the 1970s and fell prey to high inheritance taxes after the death of founder Donald Valle in 1977, eventually closing in the 1980s. The large-scale Mid-Century design of the buildings, like those pictured below, also contributed to high overhead costs.

Valle's Steak House, Springfield, MA. Circa 1970s.

The former Valle's Steak House, Albany, NY, had a similar design to the one in Springfield, MA., now Bryant and Stratton College.

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The Transsexual Skyline Squatter

After being sold, the Skyline reportedly didn’t remain open long, though how long is not known. Access to Catskill phone books from the era would help solve the mystery. Typically, one can find those at a local library, but that would require about an hour drive each way (ironic, since I once worked across from the Catskill Public Library for several years). While continuing my research on what happened to the Skyline after it closed, I came across a cryptic Facebook posting noting that two individuals squatted on the Skyline property for a short time (presumably before the fire). Their names were John Paul and Dawn Langley Simmons.

John Paul and Dawn Langley Simmons. Credit unknown.

At best, squatters are desperate people looking for a home and, at worst, con artists looking to rip someone off. Often, they’re somewhere between the two extremes. What I thought unusual is that after 45-50 years later, someone still remembered the squatters’ names. Generally, the names of squatters are quickly forgotten, not to mention nearly a half-century later, so that if someone remembered their names for so long there has to be bigger story — and, boy, was there ever.

As it turns out, Dawn Langley Simmons, from Charleston, South Carolina, was named Gordon Langley Hall at birth and was born intersexed. Assigned male, she consequently went through a sex change operation. Hall, a White woman, married John Paul Simmons, an African American man (alternatively described as a chauffeur, mechanic, and sculptor) in 1969. Interracial marriage in South Carolina (where the Simmons married) was illegal until 1967 when the Supreme Court declared anti-miscegenation laws unconstitutional. In fact, at the time of the decision it remained illegal in all former Confederate states (plus Delaware), though a number of other states only repealed those laws in the few years before the 1967 decision. To its credit, New York, along with six other states, never had any anti-interracial marriage laws on the books in its history.

John Paul and Dawn Langley Simmons on their wedding day. Credit unknown.

Looking for more accepting environs, the Simmons headed north. According to a The New York Times article, “Transsexual Starting New Life in Catskills,” Nov. 23, 1975, the couple moved into a former gothic home where President Martin Van Buren, who lived in nearby Kinderhook, was married. The Simmons had plans to restore it, but left or were evicted for non-payment of rent, leaving the home reportedly “an empty wreck.” I suspect employment for an interracial couple, one of whom was transgendered and had been featured in a recent New York Times article, was challenging in small-town Conservative Catskill.

The Simmon’s purported squatting in the Skyline, if true, seems like it could have been another attempt gone bad to restore a building. If so, it likely occurred after 1975 since the Times article does not mention it (and such an incident would be relevant to the story), but before 1982 when the Simmons divorced. The fire must have happened after the Simmons left the Skyline, if indeed they were there.

After this difficult period of her life, Hall would go on to author a total of 20 books, novels, biographies, and children’s books.

Concluding Thoughts

Matchbook.

I have a fondness for old buildings, even the ones no longer there, as covered in my essay, Novak Bowling Supplies, Avenue A, in which I explore where the old shed that contained the aforementioned bowling business once stood and tracked down who owned it and what became of him. Likewise, with both family and friends having been involved in the restaurant business, I have a fondness for the history and drama behind the scenes in food service as covered in my previous articles, The Last Days of the Metro Diner and The Rise and Fall of Big Dom’s Subs. I tried to unearth as what information about the Skyline as I could, but there are few print sources available on the internet, and not much on social media, so much of the information I seek would probably be found through oral histories by speaking with those who recall The Skyline Restaurant and Terrace Lodge, but I would have to live in that area to maximize that effort.

There is a lot more that could be dug up about the Skyline, and I suspect it would be no less dramatic, or sentimental, than it was for the Metro Diner and Big Dom’s Subs — though, admittedly, with a much better menu and view.

Sunset Over Olana and Rip Van Winkle Bridge by Kenneth Salaz - Art Renewal Center.

 

Note: Anyone who ever ate at, worked at, or knows any of the lore surrounding the Skyline Restaurant, please share your comments below!

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