[2] The Boston Draft Riot of July 14, 1863, began on Prince Street.

[3][4] In the 20th century, the street became notable as the headquarters of the Angiulo brothers,[5][6] the leading Italian-American crime group in Boston from the 1960s until the mid-1980s.

[12] Giovanni and Cesare Angiulo, the brothers' parents, lived across the street at number 95.

[13] In January 1981, FBI agents placed bugs in Angiulo headquarters for over three months and listened to their discussions about murder.

[14] DeFilippo Playground and RUFF North End Dog Park occupy part of a triangular plot of land between Prince Street and Snow Hill Street.