Woodstock’s Mill Hill Road – Before the Deluge

Back before Duey’s.

As the curtain rises each morning, the stage that is Woodstock is once again revealed.  And, like a continuous play with a revolving cast, the town enters yet another day. Naturally enough, as we head through town with much on our minds, we pass structures we seldom give a second thought to. And, certainly, least in our thoughts is who or what once occupied the buildings we pass in a Woodstock that went before.

Change, they say, is inevitable and Woodstock has not been immune. Over the years, while Woodstock’s architecture has gone mostly unaltered, the center of town has morphed from a small village with a collection of businesses and private homes into a commercial hub sought out by an ever-increasing number of visitors — and entrepreneurs 

And yet, for many Woodstockers, the storefronts we pass today still echo with the wares they once dispensed and the faces of those who unlocked their doors each morning. So what was Woodstock like in the years before we lent our name to a generation? What, for this purpose, might Mill Hill Road have presented to the passerby before the world “found” us in the years prior to a certain festival? (Even though we were doing quite well, thank you.)

Physically, many of Woodstock’s central features and structures along Mill Hill remain the same, beginning with the gateway to the town. Golfers, such as this author, have been slicing balls onto Route 375 since 1929. Across 212, where Cucina holds forth today, the original Risely farmhouse has served as host to a number of bars and restaurants over the years. The late fifties/early sixties would have presented The Townhouse to visitors entering town — though its name was whispered quietly by a community not yet eager to deal with questions of sexual identity. Much later, Woodstock’s most iconic restaurant, Deanie’s, would, following a fire at its original location further up Mill Hill, relocate to the site for a final run. Next door, the original Woodstock Playhouse rose to complete the vision of Robert Elwyn in 1938, serving as an integral link in Woodstock’s cultural DNA throughout the postwar era and beyond. Taken by fire in 1988, it has risen again to welcome residents and visitors alike. 

Inside the Woodstock Playhouse, 1930s.

Across from the Playhouse (where the Woodstock Tattoo parlor is today) once stood the domain of Louie Lewis. Lewis, the proprietor of Ye Olde Junk Shoppe (aka: Lewis Art Gallery) — a somewhat open/barn-like structure — once played football at Commerce High along side Lou Gehrig. Locally, he was often at the center of Woodstock’s political life, serving as chairman of the local Democratic Committee in a town dominated by Republicans. 

Immediately next door, overlooking the Sawkill, breakfast, lunch and dinner could be ordered up at Miss Mary’s. An advertisement from the period proudly proclaims “sea food, clams and cocktails by Eddie Logan.” Continuing along the row of storefronts that presently houses a series of shops including Print Express, Warren Hutty, yet another Woodstock force operated multiple businesses, including the Robert John Shop and Hutty Real Estate. 

Remember the A&P?

As we cross the street to where Sunflower and the Bradley Meadows plaza sits today, the reader should imagine a field without structures; a setting, often occupied by artists and art classes, delivering one of the more impressive, unobstructed views of Overlook. Once a wide open space, the plaza that is today came into existence in 1965 and would, upon opening, initially, house a bank and an A&P supermarket. Later, in 1968, Joe Forno would move his Colonial Pharmacy to the plaza while the Woodstocker restaurant would soon offer a mix of food, coffee, poetry and music as Kermit Schwartz’s Sound In, an audio equipment store occupied the end space. 

Heading up Mill Hill to where Cumberland Farms stands today, we come upon a site that was radically repurposed. In its earlier days, Sarah Cashdollar operated the Homestead there, a boarding house that often catered to visiting artists and theater folk in town for performances at the Playhouse. At some point, the home was demolished and, in its place, a Gulf service station rose. 

Ken’s Exxon, now Catskill Mountain Pizza.

Actually, this would be a good place to stop and note that Mill Hill Road, at one time, offered up four gas stations. (In 1965, Alf Evers dubbed it “Gasoline Alley.”) In addition to the Gulf station, the site of what’s now Catskill Mountain Pizza once housed Charlie Kullman’s Garage. Later the site would dispense repairs and gas under the operation of Ken and Dodie Reynolds. Anyone with a Volkswagen or foreign car in need of repair will clearly remember the good-natured abuse dispensed by Ken. 

Across Mill Hill, where Wok-n-Roll operated, is a more complicated story; a story that includes a Mobile gas station that would later become a Stewart’s ice cream shop. To the far right of the complex (before it was all connected), locals moved daily in and out of Dot’s — later Duey’s (where the Duey burger and a bucket of chicken could be had.) Back across the street, where the current Woodstock Garage is located, one would find Lou Wilson in his own Woodstock Garage, offering gas, service and a place to purchase a new Ford. Later, in 1968, it would become an ARCO station. Finally, we come to Peper’s Garage. Begun as a blacksmith shop by Henry Peper, the operation would expand over the years to include the construction of the front brick building that currently houses Sparkle. In the rear building where Maria’s now operates, it is said that the first meeting of Woodstock’s American Legion was held. As one faces the building, the house to the right was the home of the Pepers where Miss Florence Peper, Henry’s daughter lived, gardened and attended church well into the 1990s directly across the street at the Lutheran Church.

Retreating a bit down Mill Hill, the building that now operates as the laundromat once was home to well driller, Harold Lapo. It is said that that the small shop in the back was where Mr. Lapo kept his prized Cadillac. Just down Elwyn Lane a little further, where Dr. Dinapoli practices, little has actually changed, as the building was once home to Dr. Hans Cohn (who served Wodstockers for 23 years, performed as a cellist and served on the board of the Maverick) and, later, was the office of Dr. Kenneth Bremmer.

Back out on Mill Hill and across the way where CVS sits today is the site that once housed Woodstock’s two-room schoolhouse. The schoolhouse was later moved behind the current building to make room for Woodstock’s Grand Union supermarket.  Before becoming a private residence, the schoolhouse lived on as Harrison Muller’s School of Dance and, later, as Woodstock’s first youth center.

Traveling a bit further up the same side of the street, past Wok-n-Roll, we come to the building that now houses Silvia’s. For any Woodstocker of longstanding residence, it is remembered, of course, as the iconic home of Joyous Lake (1971). Prior to the Lake, however, the building’s history includes Elwyn’s grocery store, a restaurant and, as recalled fondly by many who grew up in Woodstock, Charlie’s Ice Cream Parlor, owned and operated by Mr. & Mrs. Charles Goodrich. 

Deanie’s, after the fire.

Stepping outside the door of Charlie’s (later named Rick’s), one would only have to wander a few paces across Demming Street to enter Woodstock’s most fondly recalled restaurant, Deanie’s (“Known from Coast to Coast”). Built and operated by Deanie Elywn, Deanie’s, perhaps more than any other establishment, symbolized the Woodstock that was in the fifties and sixties. First operating as a restaurant, a bar was added in 1948 and, in 1950, a second floor was constructed. There, the local plumber, artist, off-duty constable, craftsman, musician and a few politicos could be found huddled together over one last drink before Flo Odell’s piano played them home. Fire brought an end to the good times on Mill Hill Rd. in 1974.

Moving up the street to the red building that sits back from the road where Castaways is today, we find the site that once housed Woodstock kindergarten classes. Directly across the street, home today to Catskill Art Supply, Donald and Elise Twine held forth with Twine’s Catskill Bookshop. 

Back across the street, where Bread Alone opens each weekend to a line of visitors and locals alike, lines also once formed to attend the opening of the newest art exhibit under the watchful eye of Lillian Fiolic at the Rudolph Gallery 

The Longyear Building, corner of Mill Hill and Rock City Road.

Crossing Maple Lane to where Candlestock is today, one would be greeted, should you have chosen to knock on the door, by Woodstock’s Reverend Harvey Todd. The building once served as the parsonage for the Reformed Church on the Village Green. Next door (Pegasus today), the first floor offered one of Woodstock’s few clothing stores, Bonnie’s, where its owner, Bonnie McManis, offered the latest in lingerie. Upstairs, Irving Kalish worked the local real estate market as locals and tourists alike passed beneath his Irving Kalish Real Estate sign.

The building that is now, once again, The Pub, has long existed as a home for libation and food. (My father would always refer to it as the Swayback Tavern…look at the roofline.) While, at one time, it operated under the ownership of Bill and Janet Dixon as The Irvington, many remember it today as always being The Woodstock Pub under the ownership of Chris Lynch and, later, the Scales family.

Stowey Stowell in front of his establishment.

Finally, for Mill Hill Road — at the corner of Rock City Rd. — we arrive at a series of stores housed in what is known as the Longyear Building. While the Longyear Building itself dates back to 1933, in the late 1950s/early 1960s the building was home to Allen Electric, Victor Basil — Hairdresser, Peggie’s Gift Shop (operated by Peg Barryann) and, on the corner, a visitor returning over time would have found a store changed more by its names than by what was offered (newspapers, candy, a soda fountain, etc.). What is now Clouds was originally known as Stowell’s (owned by Stowey Stowell), the operation would be followed by Luden’s then Schneider’s, operated by Walt and Emily Schneider.

Back across the street one last time, we arrive at H. Houst and Sons. Houst’s and the Woodstock Lumber Yard (owned by the Neher family) are the two operations that have seen the passing parade that is Woodstock for the longest time. They remain, in many ways, the anchors to Mill Hill; family operations that have met Woodstock’s needs throughout the decades while also serving as exemplars of how to give back to the community.

So, if you believe in generous spirits, Woodstock has them. Sometimes, they appear in human form whenever Woodstockers gather and remember folks such as Flo at the piano in Deanie’s or when Ken Reynolds hauled your car out of a snow bank on a winter’s night. But they can also be found in the framed timbers or masonry that we move in and out of each and every day. Combined, theirs was a community, a community doing the best they could; a community that serves as part our foundation today. A reminder, if you will, that what we create today will similarly frame a Woodstock of the future. What will they reflect on?

Author’s Note: I have endeavored to piece together the legacy of Mill Hill as best as possible. Should the reader wish to add something relating to the 1950s and 1960s — or correct an error — please e-mail me at woodstockhistory@hvc.rr.com. I will add your comments to the document that that will be placed in the archives of the Historical Society. With great appreciation to Chuck Howland whose mapping efforts and knowledge of local history greatly contributed to this article.

Richard Heppner has served as Woodstock Town Historian since 2001. His newest book, Woodstock’s Infamous Murder Trial: Early Racial Justice in Upstate New York will be published this coming winter.

Photos provided by the Historical Society of Woodstock.

Mill Hill Road, 1970s.


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