Greenfield Winter Carnival is a long-standing tradition in Greenfield and was a big thing back in the 1920s and 1930s! 100 years ago Greenfield received much more snow than we do now, truly creating a Winter Wonderland with multiple ski jumps and a toboggan chute. The toboggan chute was first constructed on Rocky Mountain in 1921 and in 1922 the Greenfield Outing Club was born. Their mission was to promote Winter Sports in the region. They also helped to construct the Ski Jump on the East Slope of Shelburne Mountain (by the Home Depot plaza) in 1926. After the jump's collapse, William Graves constructed the ski jump at what is now Abercrombie Field using timbers from the Montague City Bridge that had washed out. Before the days of highways, people flocked from all over and traveled on the Ski Train from Boston to the area for its "unrivaled winter sports center".

While we do not have all the details on these original Greenfield Winter Carnivals, their legend remains! It is estimated that 5000 spectators attended the 1927 Winter Carnival where two ski jumpers leaped through a flaming hoop off the ski jump after dark. In 1928, Greenfield Winter Carnival hosted the Eastern U.S. Ski Championships on the Shelburne Mountain Ski Jump. The 1928 event hosted by the Outing Club and Greenfield Chamber of Commerce was said to be the biggest and best in New England! In addition to ski jumping, the event also featured "fancy skating", speed skaters playing hockey on Highland Pond, a cross country ski race, snowshoe & ski hikes, a Carnival Ball at the Armory, a Fireworks Display and band at Beacon Field, and ice sculptures at the common and at private residences.