In early 2017 a group of Highland Knights of Columbus members were brainstorming to find a fundraiser for the recently refurnished baseball and softball fields. What they came up with was the start of an exciting and festive event. The Jingle All the Way Bar Crawl involves 3 things; Friendship, Competition, and Charity. Teams compete in games at local bars in Highland, IL while donning their festive, newly acquired, Jingle All the Way sweatshirts. A portion of every jolly bar crawler's entry fee goes towards their choice of 1 of 3 charities. The 2018 event's charities include Leaps of Love, St. Vincent De Paul Society, and funding for the All Abilities Playground in Highland. Following the bar crawl are live performances from great bands from the area.

What started out as a fundraiser for one noble cause became so much more! In the Inaugural year of the Bar Crawl we raised money for 3 additional charities. As the years go on, the charities will change, but the fun, fellowship, and competition will remain!