Gazette Article by: Eleanor Tippens
Appeared in the Gazette: Winter 1994

Sledding on Oak Street circa 1900, WHS Object 3163

Sledding down Oak Street hill? It seems unlikely in today’s car-filled world, but at the turn of the century, everyone got involved in the fun.

Long-time residents recall fathers and grandfathers saying that with a good push at the top – and a lot of luck—riders could go all the way to Sheridan Road, turn the corner and, some claimed, continue on as far as Cherry Street or even Willow Road.

According to Bob Humphrey (whose grandfather, Max Meyer, founded the Winnetka Bank in 1894) the secret was to have a good ice glaze on the track. The Winnetka Fire Department used its hoses to send huge jets of water down the hill. Then the sledder who could steer the straightest course made the first run down the slushy hill, determining just how straight the track would be.

The growing popularity of cars in the 1920s put an end to the sledding, and in 1938, when the railroad tracks were laid in the cut, the hill was made less steep.

During World War II from 1941-1945, car travel was limited by gas rationing, and it again became possible to sled on the streets during snowy winters. Some of the best rides were through the ravines along Sheridan Road or down “Snake Hill” between Prospect and Maple.

The Big Snow on January 26-27, 1967, brought all vehicles to a standstill, including snowplows! Life Magazine reported that it snowed for  “29 hours and 8 minutes, resulting in a total accumulation of 23 inches”. For about a week skis, sleds and toboggans became the only way to get around, and snowbound Winnetka returned to the way it must have been when sledders ruled the road on Oak Street hill.