Real estate man Charles Edmund Day (1846-1902), who also played and sold pianos and organs, named this street in 1887 on his Dayton Heights tract. Day looked to his boyhood home of Port Jackson, NY – a once-thriving village on the western shore of Lake Champlain – for street name inspiration: Clinton Street for Port Jackson’s county; Champlain Street (since merged into Temple) for the lake; Burlington Avenue (now part of Virgil) for the Vermont city across the water; Middlebury Street for another Vermont burg. Then there was Dayton Avenue (now part of Westmoreland), which like the tract itself was a play on Day’s surname. But what of Madison Avenue? That, my friends, is a mystery. There were no Madisons in Day’s family tree, no known ties between Day and NYC’s Madison Square or Madison Avenue, no Madison-themed locales near Port Jackson, and no indication that Day was especially fond of President James Madison. For what it’s worth, Dayton Heights also had Wheaton, Whitney, and Woodward avenues (since absorbed into Hoover, Juanita, and Commonwealth, respectively), and I found no rationale behind those names either. Maybe Day just liked how they – and Madison – sounded.