The Black Bear Trail, so named because it ran through the natural habitat of the black bear, was organized by The Black Bear Trail, Inc., an association of officials of Chambers of Commerce, boards of trade and cities lying along the route of the new highway, whose objective was to provide a direct, safe route to historic and scenic sites from Canada to Florida. In April 1927, members of the Association marked the new route through Maitland through what is now Highway 17-92 by placing insignia showing a black bear painted on an orange oval background on both sides of telephone poles along the road. This road joined the Dixie Highway at Lake Lily and both names described this road from this point south. When completed, The Black Bear Trail ran from Quebec, Canada to St. Petersburg and Miami, Florida, and opened to travelers some of the most scenic areas in the country.
A Florida Heritage site sponsored by the City of Maitland and the Florida Department of State.