Trailways Conference

All member schools belong to the Wisconsin Interscholastic Athletic Association.

Two private schools who had recently joined the WIAA as part of the WIAA/WISAA merger (Abundant Life Christian in Madison and Valley Christian in Oshkosh) rounded out the initial membership roster of the Trailways Conference.

[1] The fifteen schools were initially subdivided into North and South Divisions: Central Wisconsin Christian joined the conference after leaving the East Central Flyway Conference in 2004, and two years later the Trailways Conference took three more former East Central Flyway schools into the fold: Lourdes Academy, Markesan and Oakfield.

The Trailways Conference was realigned to a two-division format in 2013: In 2014, Wayland Academy in Beaver Dam joined the Trailways South Division,[7] and St. Ambrose Academy in Madison joined with Abundant Life Christian School for most sponsored sports (they would move to their own stand-alone programs in 2023).

[8] The North/South divisional alignment would last for two more years before the Trailways realigned to three divisions in 2016: This alignment would only last a single season, as Palmyra-Eagle and Parkview joined the Trailways as all-sport members in 2017 after leaving the Rock Valley Conference,[9] bringing conference membership to the current twenty-four schools and the current East/South/West divisional alignment.