Try the Chicago area schools.
My school’s teams (Loyola Academy) were the Ramblers. No we had no clue what it meant either. Note that Loyola University of Chicago, in all of it’s athletic web pages, never tries to explain what a Rambler actually is, though they do use a fairly striking wolf logo (the Academy, on the other hand, used a Viking logo. Go figure.)
New Trier: The Trevians
Mt. Carmel: The Caravan (if they didn’t keep rolling over opponents in football it would be laughable. As it is, it’s painful).
Damn!
I did find one explanation for “Ramblers” on the Loyola University of Chicago web page, but I think it’s fake, myself. Note that the reason for sharing nicknames betwen the college and the high school is the they shared facilities until 1956, when the high school moved to a new campus in Wilmette.
"As the only collegiate program with the nickname “Ramblers” for its teams, the question is often asked as to why that name was picked. The origin goes back to the days when football was king at Loyola University Chicago.
Previous to the 1920s, all athletic teams were merely assigned the school colors instead of a nickname. All Loyola teams were known as the “Maroon and Gold.”
In 1925, the football coach, along with the student newspaper, conducted a contest to name the football team. The winning entry was “Grandees”, tying into the Spanish origins of St. Ignatius of Loyola. However, the name “Grandees” did not catch on in the following months.
In 1926, a more informal but much more binding process finally gave Loyola’s teams their nickname - “Ramblers”. That year, the football team traveled so extensively across the United States, “rambling from state to state”, that the media dubbed Loyola as the Ramblers.
Despite dropping football as a varsity sport in 1930, the nickname “Ramblers” is still proudly carried by today’s athletic teams at Loyola University Chicago."
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Loyola University Chicago