When Winnetka Was the World Capital of Sledding

By Duff Peterson
Originally published in the Fall/Winter 2014 Gazette

Before organized activities came to dominate the lives of Winnetka children, one pastime in particular enjoyed immense popularity here: sledding. Winnetka’s long winters and steep terrain provided ideal conditions, and along with skating on the Park District’s three natural ice rinks, sledding was the main form of recreation for Winnetka kids in the colder months.

Between Lloyd Park and the southern end of town, Winnetka is blessed with two ridges created during the final phase of the Ice Age. One is today’s Lake Michigan bluff. The other is a moraine formed about 14,000 years ago when the level of the lake was 60 feet higher than today. The moraine angles off from the present shoreline starting at Lloyd, running almost due south through downtown Winnetka, North Shore Country Day School and Indian Hill Club, providing high ground for the present course of Ridge Avenue and, in earlier times, the Green Bay Trail.

Although Winnetka’s winter weather varies considerably from year to year and even from day to day, the Village often experiences significant snowfall, especially when cold northeast winds travel over the relatively warm expanse of Lake Michigan, creating “lake effect” snow. Winter temperatures regularly stay below freezing for long periods, allowing snow to settle without melting.

For many years, Oak Street (above) was Winnetka’s premier sledding run. During the winter, the Village blocked off the street east of the railroad tracks for a few hours in the afternoon and evening, and after a good snowfall, applied water to the street, creating an icy track. With a good push, a fully-loaded sled could go all the way from the top of the hill to Sheridan Road, turn right and continue for two blocks south on Sheridan. Always in need of riders, the North Shore Line advertised the Oak Street run in Evanston in 1906, attracting what one local newspaper called a “rougher crowd” to the hill. (The railroad denied stirring up trouble in the next issue.) But despite the occasional presence of ruffians from Evanston, Oak Street was the place to be on winter afternoons in Winnetka’s early days.

As automobile traffic increased in the early twentieth century, coasting on Oak Street became more and more dangerous, even when the street was blocked off, and more and more of an inconvenience for motorists. In January 1923, the Village council decided to discontinue closing Oak Street, and designated Park Avenue as the Village’s coasting hill. Park Avenue is a short street running downhill from Prospect to Maple, laid out before 1890 as part of the Winnetka Park Bluffs Subdivision. The Winnetka Weekly Talk happily noted that the street would be “permanently barricaded and the incline iced and a track cut . . . Park Avenue will be reserved for the children.” The barricade was erected in January 1924, and for several decades after that, Park Avenue was a popular sledding run for youngsters from all over the Village, who dubbed it “Snake Hill” because of its S-curve shape. At the top of the hill, the south side of Park dropped steeply into a gully that offered short side-descents. With a running start, a sledder could fly down Snake Hill and into the park below it, going almost to Sheridan. For days or even weeks on end in the winter, local children enjoyed many hours of unsupervised fun on this quiet street.

The sled of choice for kids on Snake Hill was the Flexible Flyer, first patented in 1889 by Samuel Leeds Allen, an inventor of farm implements from New Jersey. Allen’s masterstroke was to attach a cross piece at the front that allowed the rider to steer, and with proper body position, tight turns were possible. The Flexible Flyer performed best on settled, hard-packed snow; in deep snow conditions, kids brought out “saucers” and other smooth-bottomed conveyances, but lacking a steering mechanism, these were not optimal for negotiating the S-curve of Snake Hill or avoiding the steep side-gully. The Flexible Flyer is still in production today, unchanged from its original design.

For a little variety, kids ventured beyond Snake Hill to the ramps of Maple Beach and, after the Village acquired it in 1964, Lloyd Beach. In icy conditions, a sledder could attain exceptionally high speeds on the north ramp at Lloyd, but had to execute a very sharp turn at the bottom, a challenge even on a Flexible Flyer, and a flat-out run on ice sometimes ended in an unexpected collision with the ramp’s steel retaining wall. Another source of excitement was sledding down the south ramp at Lloyd and out onto the ice of Lake Michigan, with kids competing to see who could end up closest to the frigid and sometimes roiling waters without falling in.

Adventurous young Winnetkans thought nothing of trespassing on private property along the moraine in search of the perfect sledding run. The steepest terrain was between Park and Humboldt, and exploring these “back bowls,” steering sleds through groves of evergreen trees, and bashing though piles of leaves, was great fun. Property owners rarely if ever shooed young sledders off their land.

In recent years, the growing popularity of other winter sports, the more efficient plowing of streets after snowfalls, and shorter and warmer winters have put an end to Snake Hill as a sledding slope. The barrier at Prospect became truly permanent within the last 20 years when the upper 100 feet or so of pavement was torn out and grass and shrubs planted. Today an increasingly mature forest grows in exactly the place where for more than 50 winters, children jumped on their sleds for a thrilling downhill ride.

Skokie Coasting Mound, 1973, courtesy of the Winnetka Park District

Winnetka’s most popular sledding run, even more popular than Snake Hill, was the “coasting mound” at Skokie Playfield that the Winnetka Park District operated for more than 30 years. The coasting mound was about 30 feet high, constructed during the fall of 1950 using 9,000 cubic feet of clay taken from a sewer excavation nearby and then covered with another 1,000 cubic feet of topsoil. The mound was an instant success, the Park District reporting that 535 people visited it on a single Saturday in January 1951. The Park District soon added lights borrowed from a nearby baseball field, allowing coasting at night.

During the first few weeks of the mound’s operation, tragedy struck. Two 10-year-old boys suffered skull fractures when their toboggan, also carrying a 22-year-old Northwestern student, collided with a Park District tractor at the bottom of the hill. One of the boys died of his injuries 10 days later. The incident prompted the Park District to impose safety measures on the mound, including placing an attendant at the top (for whom a small hut was constructed), dividing the coasting face into lanes, and constructing gates to regulate the flow of downhill traffic.

A wooden toboggan track was soon built along the side of the mound’s coasting face, while the rest of the slope was open to sleds, saucers and any other conveyance that kids might use to hurtle down a snowy hill. Many Winnetka families owned a toboggan, a flat-bottomed wooden sled based on traditional Cree and Inuit designs. A toboggan could travel very fast down a track like the one on the Winnetka mound but could not be steered, and had no brake. During the 1957-1958 season, the coasting mound was open for 57 snow days, while during the following season, the mound saw a total of 14,400 visits over 49 snow days.

The Park District removed the coasting mound in the early 1980s to allow reconfiguration of Skokie Playfield’s baseball diamonds, the addition of two paddle courts and improvements to the golf course. Another smaller sledding hill was removed in 2012. The coasting mound, such an important part of Winnetka winters for more than 30 years, is now only a memory.