by G. Jack Urso
 |
| The Skyline Restaurant and Terrace Lounge in the mid-1960s. All interior and exterior images of the Skyline are from period postcards. |
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 lay throughout the Hudson River Valley.
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, mid-1960s.
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.
.bmp)
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 early 1990s.
 |
| The ruins of the Skyline Restaurant before demolition. Some fire damage on one beam can be seen. 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’s
menu is a model of Mid-Century American dining — for meat eaters. 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 equivalent 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 the 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.
a.bmp)
The bar at The Skyline Restaurant and Terrace Lounge, mid-1960s.
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.
________________________________________________________________
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 Steak House. 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 Modern 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 Modern 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 (Nov. 2024). The covered carport in front of the entrance, visible in the photo above, has since been removed here, though the exterior is otherwise unchanged. |
________________________________________________________________
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. |
I wasn't sure if that was a figurative or literal reference to squatting, but I thought it unusual is that after 45-50 years later, someone still recalled their names. If someone remembered them for so long there has to be a bigger story — and, boy, was there ever!
As it turns out,
Dawn Langley Simmons, born and raised in England and later moved to Charleston, South Carolina, was named Gordon Langley
Hall at birth. Born intersexed, but assigned male, she consequently went
through a sex change operation as an adult. An
experienced editor and prolific author, Dawn wrote several books before her
move to the Catskills in the 1970s, funded, presumably, by her success in
publishing.
Dawn, 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. 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 abandoned the property when a book deal Dawn was working on fell through and they were unable to complete the sale, leaving the home, reportedly, “an empty wreck.”
The Simmons’ 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, Dawn returned to Charleston and went on to author a total of 20 books,
novels, biographies, and children’s books, before passing away in 2000. John-Paul moved to Albany, NY, continuing as an artist, and passed away in 2012. In his obituary, though long divorced, Dawn was still listed as John-Paul’s “predeceased wife.”
Concluding
Thoughts
.bmp) |
| 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 articles The Last Days of the Metro Diner and The Rise and Fall of Big Dom’s Subs. I tried to unearth 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 the information I sought would
probably be found through oral histories by speaking with those who recall The
Skyline Restaurant and Terrace Lodge, as well as the local library and newspaper archives, but I would have to live in the area to do that.
There’s 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.
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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