Of all the streets that Charles Day laid out on his Dayton Heights tract in 1887, only three have kept their original names: Clinton Street (see that entry for some background on Day), Madison Avenue (see that entry for more about the tract), and Middlebury Street. Charles Day was born and raised in Clinton County, NY, across Lake Champlain from Burlington, VT, so he must have been feeling homesick when he named Clinton Street and the now-defunct Champlain Street and Burlington Avenue. In this context, Middlebury Street presumably owes its name to Middlebury, VT, despite that city being a little further afield. It might have also been an inside joke, since it cut through the middle of Dayton Heights. Day certainly wasn’t against a little wordplay: “Dayton” was an obvious spin on his surname.
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