Twilight director Catherine Hardwicke flew out to Pittsburgh to meet Kristen Stewart on her day off from filming Adventureland to audition her for the role of Isabella Swan, which she won and accepted.
Crews were hired to remove and hide snowfall and snow accumulation during filming because the film was shot in the winter months. In some indoor scenes, extras were paid to block the windows and doors so the snowfall wouldn't be visible on camera.
A total of 41 songs were licensed for use in the film, but only 14 made the film's accompanying soundtrack. Most songs used are from the 1980's but to fit the time frame songs from the 1960's and 1970's were also utilized.
Adventureland was filmed in Pittsburgh, PA. The amusement park in the movie is known as Kennywood Park. The rides shown in the movie are actual rides, although the names of the games have been changed.
In early versions of the script, the musician idolized by James (Jesse Eisenberg) and many of the surrounding characters was Neil Young. Originally it was written that Connell (Ryan Reynolds) had played alongside Young and was idolized by the characters. The musician was eventually replaced with Lou Reed, the late singer of The Velvet Underground.
There are several easter eggs on the film's Blu-Ray release including an unseen clip from Ryan Reynolds and a clip of Kristen Stewart creating an elaborate plan to sneak into the Razzmatazz dance club.
Long after most photography on this film was done, an important NYC rainy street scene was shot on Ludlow Street between Grand and Hester, just a few doors down from where Lou Reed and John Cale lived and worked as part of The Velvet Underground.
When James is dumped by Arlene in the first scene, one of his friends says "You didn't tell her about the scarlet V, did you?", indicating that James is marked by a V as he is still a virgin. This echoes the novel, "The Scarlet Letter" by Nathaniel Hawthorne, where Hester Prynne has to wear a scarlet A to mark her as an adulteress.
James Brennan's mixtape, labeled "J's FAVORITE BUMMER SONGS" has 9 tracks on it and is seen fleetingly for 2 seconds on the dashboard in the car at 33:53 approx. All the tracks names are visible. Pale Blue Eyes by the Velvet Underground and sung by Lou Reed is playing during the scene and it is track one on the mixtape.
The trivia item below may give away important plot points.
In the scene when Brennan and Em are going to eat the marijuana cookies, Joel (Martin Starr) is about to try one as well before noticing the nuts and exclaiming "Walnuts? Do you want to see me go into anaphylactic shock?" Starr's character in Freaks and Geeks (1999) had a nut allergy and went into anaphylactic shock in the episode Freaks and Geeks: Chokin' and Tokin' (2000).