We explore Halloween as a uniquely constructive space for engaging racial concepts and identities, particularly through ritual costuming. Data were collected using 663 participant observation journals from college students across the U.S. During Halloween, many individuals actively engage the racial other in costuming across racial/ethnic lines. Although some recognize the significance of racial stereotyping in costuming, it is often dismissed as being part of the holiday's social context. We explore the costumes worn, as well as responses to cross-racial costuming, analyzing how “playing” with racialized concepts and making light of them in the “safe” context of Halloween allows students to trivialize and reproduce racial stereotypes while supporting the racial hierarchy. We argue that unlike traditional “rituals of rebellion,” wherein subjugated groups temporarily assume powerful roles, whites contemporarily engage Halloween as a sort of “ritual of rebellion” in response to the seemingly restrictive social context of the post-Civil Rights era, and in a way that ultimately reinforces white dominance.