Among the crowd at the parade are: Steven Wright, Marvelous Marvin Hagler, Conan O'Brien, Carla, Cliff and Norm from Cheers, U.S Senator Elizabeth Warren, Michael Dukakis (dressed as a tank) Fred the Baker, Mark Wahlberg, Steven Tyler, John Houseman, the Ghost of Sam Adams and the New Kids on the Block.
When the Simpson's move to Boston, the theme of St Elsewhere is playing. St. Elsewhere was a medical drama black comedy television series based in Boston.
Whitey Bulger makes a cameo at the parade as well as the manager of the bowling alley.
A sign referencing the now-defunct Boston radio station WBCN 104.1 FM is shown over the Cumbies store. Futurama (1999) voice actor Billy West used to work on-air at it.
The Statue of Red Auerbach can be seen while the Simpson's visit Quincy Market.