That reminds me of the trapezoidal Chrysler Building[1] in NYC, shaped by a plot boundary reflecting the pre-grid Boston Post Road[2] (only 2 weeks NYC-Boston!). The Road elsewheres reflects 1600's colonial improvements to the earlier Pequot Path, and influenced US1 et al.

[1] https://ephemeralnewyork.wordpress.com/tag/chrysler-building... [2] https://en.wikipedia.org/wiki/Boston_Post_Road