A Century of Tobogganing on the Snowy Streets of Litchfield Is Recalled in a Postcard Photo and More

By Gavi Klein

Photo credit: Courtesy of Litchfield Historical Society

Snow days might be a thing of the past, but hopefully Litchfield’s legacy of tobogganing down snowy streets is not. Our first big snow of the year harkens back to the days of sledding down town streets in chilly glee—this 20th century postcard photograph, depicting Litchfielders tobogganing down East Street behind St. Michael’s church, represents a nostalgia that born-and-bred Litchfield folks know well. Long-time residents recall tobogganing down Litchfield streets back in the ‘50s, ‘60s and ‘70s after massive snow storms—but the above postcard photo was likely taken sometime in the ‘20s, as it is addressed in 1924. However, even before that, tobogganing has been a wintertime Litchfield tradition on those white-blanket days. The Toboggan Club was founded in 1886, leading to the building of a massive slide down Prospect Street. The club was so popular that young people as far as Woodbury were known to come to Litchfield for a spin. Even before that, in 1799 Jane Watkinson, a Litchfield resident, recalls to her brother in a letter (currently at the Litchfield Historical Society), “Hannah, and one of our boarders and myself went yesterday after school and bespoke a sledge to slide down hill on, and I promise myself much pleasure this evening from that amusement.” Here’s hoping that this year we’ll get enough snow to bring back this cherished Litchfield tradition!