In 1999, a few local runners banded together to form a committee to pursue Dixon hosting a 5K race. The ideal time of the year to do that was during the Annual Petunia Festival held each year during July. Working with various businesses and civic organizations, the inaugural event was held in 2000.

An active part of that inaugural year was the sponsorship provided by many of the local businesses. With their support and encouragement, a large group of runners from near and far raced through the city streets of Dixon, IL.

That first year brought a variety of age groups who participated. The fellowship of the runners still continues today with many of those original Reagan Run runners still racing against each other and the clock.