Old Winter Pastimes in Sleepy Hollow & Tarrytown

By Henry John Steiner

 Historian of Sleepy Hollow, New York

 “Where are the snows of yesteryear?” I can remember the giant icicles hanging, almost to the ground, from our house at 245 Crest Drive. Chunks of black cinder mixed with the snow along the edge of the street. Was it a morning in 1956? After a deep snowfall, the traffic noises were stilled—even the jingling syncopation of the chain-clad milk truck was quieted. In the general silence, the only sound was the crunch of my boot on the crystal snow.

Boot snow crust Sleepy Hollow

Boot snow crust Sleepy Hollow

But before I got too comfortable in my reverie, a snowball would buzz by my ear. There was Geoff Herguth from next-door, freckled and smiling, egging me on to combat. Our driveways lay side-by-side, so shoveling them produced a high mound of snow at the curb that could be tunneled through. The little snow fort served as a position from which we could ambush innocent and unsuspecting passersby.

Henry John Steiner

The writer cross-country skiing in Sleepy Hollow’s Rockefeller Preserve

My father helped his four children to pile up a sledding run on the hillside behind our house, but for more serious sledding there was the sloped lawn across from the Herguths. My sister Liz Ann remembers the sensation created in the late 1950s by the introduction of the space-aged, aluminum “Flying Saucer.”

Lorraine with friends and snowman 1950s Tarrytown

Lorraine with friends and snowman 1950s Tarrytown


Liz, Lorraine, & Mary M. skating on Tarrytown Lakes early 1960s

Liz, Lorraine, & Mary M. skating on Tarrytown Lakes early 1960s

I forget when we took our first skating trip to the Tarrytown Lakes, but by 1959 the Steiner kids were doing it regularly when the ice was thick enough. There was something unique about skating at The Lakes as a kid; I think it had something to do with being together with so many friends, neighbors, and new faces. It was odd to see all those young people brought together for one purpose–to have fun. It was a community event and a community recreation, where all were free from even the slightest reminder of the duties and cares we left at our homes or in town. Instead we had glorious nature all around us. The lake was beautiful in the sunlight, or mysterious in the dark, with the signature sounds of steel on ice, the raising of young voices, or the clomping of skate blades on the wooden floor of the warming hut.

Mom in snow, Tarrytown 1950s

Mom in snow, Tarrytown 1950s

Liz Ann remembers, “There were lots of opportunities to socialize, or show off new skates—with or without fancy pompoms. At one time they had hot chocolate at the hut.” She recalls a well-organized safety patrol that controlled the “infamous” whips or chains of skaters that swept over the ice. The skating area was so big that there was usually plenty of room for pick-up hockey matches and the figure skaters doing their figure eights. “If it was light enough,” she said, “mom or dad would walk us down to the lakes and then come back for us in the car.”

A community event

A community event

One afternoon we arrived at home and Liz Ann switched on Dick Clark’s daily TV show, “American Bandstand,” showcasing some of the hit songs we had been listening to as we skated at The Lakes. Over the years between 1959 and 1962 many “immortal” songs were broadcast from the pole-mounted speakers on the shore: “The Chipmunk Song,” “Mack the Knife,” “The Duke of Earl,” “Danke Schon,” “Peppermint Twist,” “The Lion Sleeps Tonight,” “Walk Don’t Run,” “Who Put the Bop?” “Take Good Care of My Baby,” “I’m Sorry.”

We would go back to The Lakes in the evening, where I would see friends from Washington Irving Junior High School. My late younger brother, Steve, remembered that, “the skating was illuminated to a point and then trailed off into utter darkness. Older groups and dating teenagers hung out in the shadows, and there were the forbidden areas of the ice where small streams and springs entered the lake. The ice conditions were bumpy and natural (no Zamboni).”

My sister, Lorraine, wrote, “Yes, The Lakes were a highlight of the wintertime, and it was always freezing out there. The shack where you could warm up was not all that warm, but we went in anyway to thaw our frozen toes. Of course, it is where you could see all your friends. My friend across town skated at Pennybridge (Lagana Field), where they froze the tennis courts.”

In early 1960s, we moved to Walden Road in Wilson Park. Lorraine says, “I remember sledding on the field at the bottom of Walden Road and Beach Lane. I see someone has built a house there now. Later, we went to the Rockefeller land beyond Wilson Park [the old Our Lady of Victory property] to sled down steep hills.” In the mid-60s, I myself would go tobogganing with high school friends on the fairways of Sleepy Hollow Country Club. No one seemed to mind…

The Lakes were first illuminated for skating in December of 1922, although folks were no doubt skating there from the time the lakes were first established, in the late nineteenth century. A few statistics: in 1981, there were thirty days of skating at the Lakes with eleven inches of ice; in 1977, there were fifty-five days of skating on sixteen inches of ice. The warming hut was built some time in the mid to late 1950s, and it was in recent years renovated as a local Eagle Scout project. Apparently, a minimum of four inches of ice is needed to open The Lakes to skaters. In 2005, the lakes were open for eight days; in 2004, there were twelve days of skating, and in 2003, twenty-one days.

There were other places for local folks to skate, like Fremont Pond where the older kids would make a fire on the ice for warming up, also Andrews Lane, Lagana Field, and even the Hudson River. The History of the Tarrytowns (Canning & Buxton) tells us that at least one early-twentieth-century skater, George Boock, would race with trains that passed along the Hudson River shoreline. In the first half of the century, the villages of Sleepy Hollow and Tarrytown had their share of talented figure skaters, like Silas Tappan and Wesley Jackson. Two early graduates of Washington Irving High School became champion speed skaters—Elsie Muller and Ruth Richards of Tarrytown Heights were exceptional athletes. Muller captured eleven national titles and competed on the U. S. Olympic Team.

Winter fun could have its dangers. There were bobsled races on Valley Street, and during a championship competition, in 1914, the bobsled Blitzen collided with an American Express sleigh in front of McGirl’s Hotel injuring seven bobsledders. Norma Herguth recalled being injured as a little girl. While she was “coasting” with her sled on a Philipse Manor street, she was hit by one of Husted’s coal trucks. In the early twentieth century there were coasting fatalities on both Farrington Avenue and Valley Street. One winter Norma and some friends tried walking across the Hudson River ice to Nyack, making it half way with near fatal results. In the winter of 1907, there were many accounts of Hudson River crossings on the ice, by foot, on skates, by sleigh, by Packard (four to five minutes each way), and by bicycle! This kind of crossing continued into the late twentieth century, until either there just wasn’t enough ice, or people got wise that it might be a tad risky.

Two cars on ice at Sleepy Hollow Lighthouse

Two cars on ice at Sleepy Hollow Lighthouse

To villagers of the twenty-first century, the idea of sledding on the street may seem a bit strange, but it was long a local practice—from Jenny Prince Black’s rides down Sunnyside Lane in the late 1800s, to Sara Mascia’s death-defying runs down Rose Hill in the late 1900s. Either our road crews got too efficient or our kids got more careful, but these days street “coasting” seems to have disappeared. The front lawn of Sleepy Hollow High School was a popular slope, but the recent improvements to the high school have taken it off the list. Shawn Pierpoint, a Sleepy Hollow High School graduate of a few years back, remembers walking with his snowboard to Rockwood Hall when he lived on North Washington Street. Rockwood Hall is also where my daughter, Lucie, went to sled, and that long slope with its magnificent river view still attracts cross-country skiers and “coasters” of all sorts.

Sleigh bells...

Sleigh bells…

Where are the sleigh bells of yesteryear? Those of us with good imaginations can still hear them. For the rest of us, the only sleigh bells we hear are the recorded ones that are heard in advertisements before the holidays—by the time the real winter begins in earnest—the sleigh bells are gone.


©2008-2016 Henry John Steiner


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  1. Ed Murphy

    Hi Henry, As always I drink up you comments about my old home town. Sleigh riding for me took place mostly in the Two Manors. A favorite for our group was the hill by the old Sleepy Hollow Manor Club, later renamed the “Tappan Zee Racquet Club”. Down that hill and across the little bridge where Fremont Pond drains over the waterfall. There was only a dirt road from that point to Philipse Manor in the early days. Hot Chocolate and Cinnamon Toast in the Club afterwards was a delight. Skating on Fremont Pond and hockey games were such fun. At night the sharp report of the ice cracking was an experience I will always remember. The older guys who had their girl friends with them took advantage of the sharp reports to cuddle up with their “Frightened? ” girls. Or memory being what it is, it may have been the guys who were afraid?
    My first attempts at skiing were on the Rockwood Hall slopes.

    The few long flat-bottomed light sleds,” toboggans” we called them, were not the heavy two runner types from earlier days, Made usually of thin boards curved up at one end, they appeared at the Sleepy Hollow Country club more frequently than in the Manors. My favorite sport was attaching a couple of” Flexible Flyer” type sleds together and being towed through Phiipse Manor behind a car. NOT a wise decision, but exciting as the dickens if you were number three or four. Corners often resulted in the last couple of sleds being overturned. Fortunately the snow pack on the roads was good enough to cushion the resulting tumble. The first sled rider was the hero who breathed in the car exhaust, faced the dirty snow thrown up by the tires and chains, and who was responsible for manning the tow rope around the bumper of towing car. We depended on that individual to release the tow rope if we were going too fast, or if the pavement had a “no snow” spot etc.

    The Hudson was a scenic delight and the snow covered hills across the river presented an unforgettable picture. BUT, best of all were the weekdays when my school bus to Pocantico Hills Central could not run!
    Semper Fidelis, Henry
    Ed Murphy, NT ’45

  2. Lynda Goldman Goldberg

    WOW! Hi Henry! I am from a four generational family who resided in Tarrytown during my early lifetime in the early 1960s and 1970s in the Crest and the Goldberg family and our home growing up was 1 Ichabod Lane (known than as 80 Union Avenue (across the way from Marymount College and my grandparents lived down the way on Castle Heights Drive next to the Cooneys)….my great-grandparents settled there in the early 1930s (I think) and my grandparents lived there all their lives as well as Palm Beach County, FL (where we reside now)….Such fabulous memories of skating on the Tarrytown Lakes, going to Pierson, then Washington Irving for junior HS, then Hackley and Sleepy Hollow, my family’s four generation family hardware wholesale business namely Goldberg Wholesale Supply Corporation at the time across from General Motors near the ole’ railroad station to NYC, my Mom’s speciality bookstore which she opened with Marilyn Bregman in the 1970s on Broadway which they named “The Book Inn”, The Hackley School which I and my brother, as well as two cousins attended….some of which are referenced and/or outlined on this historian website and I thoroughly enjoyed taking a look back to the idyllic sleepy little historical “Currier and Ives” type town which I we all were so lucky to have grown up in and remember when I just now googled “skating on the Tarrytown Lakes” and found this site which brought back SO MANY MANY MEMORIES! WOW!! My almost 91 year old Dad still talks about his early years living there with his parents and grandparents there on Archer Place and Elizabeth Streets and well thank you for this website which is just GRANDE!

    • Lynda, thank you so much for your comment. I truly enjoyed hearing about your connection with the community. I’m getting ready to hatch a few more stories, so I hope you will return and partake!

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