The Sport Hill Road section of Route 59 follows an "eleven o'clock" angle that is common in that part of Fairfield County. (See Eleven O'Clock Road in Weston for an example.) Both Route 57 and Route 58 have sections parallel to Route 59.
"Long lots" were narrow strips of land, up to 10 miles long, surveyed and parceled out in the 18th century. "Upright Highways" followed the north-northwest ("eleven o'clock") angle, and "Cross Highways" (such as Cross Highway in Redding) ran perpendicular (where topography permitted).
Route 59 has a short 2-lane divided section in Bridgeport along Brooklawn Avenue.