Trailways Conference

2001-2020

When the Trailways Conference was formed in 2001, football was among the sports offered by the organization. Thirteen of the original fifteen members participated in the first season of competition (including the Fall River/Rio cooperative team), with Abundant Life Christian and Williams Bay being the only holdouts. ALCS did not offer football at that time, and Williams Bay was a football-only member of the Indian Trails Conference.^[9] Two members who were affiliated primarily with the Six Rivers Conference (Belleville/Albany and New Glarus/Monticello) rounded out the original membership roster, and they participated in the first five seasons before their exit to join the Capitol Conference for the 2006 football season.^[10] The Trailways Conference was subdivided into large-school and small-school divisions for its first season of football:

There were a few cooperative programs that were football participants during the conference's history due to the small size of some of its members, and divisions realigned frequently based on the acquisition of new member schools and changes in enrollment.

2020-present

In February 2019, in conjunction with the Wisconsin Football Coaches Association, the WIAA released a sweeping football-only realignment for Wisconsin to commence with the 2020 football season and run on a two-year cycle.^[11] In this alignment, the eight original members of the realigned Trailways Conference were Cambria-Friesland, Deerfield, Fall River/Rio, Johnson Creek, Lourdes Academy, Randolph, St John's Northwestern Military Academy and Wayland Academy.^[12] Six schools were holdovers from the previous two-division setup, while St. John's Northwestern and Wayland Academy held primary affiliation in the Midwest Classic Conference. For the 2022-2023 cycle, the Trailways Conference picked up Pardeeville from the Eastern Suburban Conference as a replacement for Wayland Academy, which dropped football before returning with an eight-man football team in 2023.^[13] In 2024, the Trailways Conference lost three members to the Eastern Suburban Conference (Deerfield, Fall River/Rio and Pardeeville) and St. John's Northwestern to eight-man football and the Southeast-8 Conference.^[14] Dodgeland and Palmyra-Eagle moved over from the Eastern Suburban Conference and one school each moved over from the Southwest Wisconsin Activities League (Parkview/Albany) and South Central Conference (Westfield) as replacements for the four exiting members.^[15] The Trailways Conference will be experiencing significant changes to football membership for the 2026-2027 cycle. Deerfield and Fall River/Rio make their return from the Eastern Suburban Conference, and Randolph will enter into a cooperative program with Cambria-Friesland. Palmyra-Eagle will be leaving the conference due to their impending transition to eight-man football and membership in the Southeast-8 Conference.^[16]

Notes