The Foundation was initiated by local businessman and philanthropist Max Gladstone who made a $10,000 donation that was matched by the Town of Winkler. The foundation was incorporated in 1988. The Foundation became active in 1994 when the Thomas Sill Foundation challenged the Winkler Community Foundation with a matching grant proposal whereby the foundation would raise $100,000 over four years and the Sill Foundation would match it. This goal was achieved and a new goal of reaching $500,000 by 2003 with a long-term goal of reaching $1,000,000 as soon as possible was set.
In 2013, Winkler Community Foundation surpassed the million dollar goal with the creation of the Gateway Fund. This brought WCF assets to over $1,587,000.
The Winkler Community Foundation continues to grow. In 2015, the Thomas Sill Foundation has presented a new challenge encouraging the Winkler Foundation’s to raise up to $50,000 in their general endowment fund and they will match at a rate of 1:2. This challenge was met at the end of 2015, thanks to the many donors during the 24 Hour Giving Challenge and the Gordon Wiebe bequest.