Gay and bisexual men (GBM) who participate in gay community subcultures have different profiles, including differing risk behaviors. We examined men's participation in gay community subcultures, and its association with risk behavior. In a cross-sectional survey, 849 GBM provided information about men in their personal networks. We devised measures of their participation in five subcultural groupings and explored their associations with sexual behavior. We identified five subcultural groupings: sexually adventurous; bear tribes; alternative queer; party scene; and sexually conservative. Higher scores on the sexually adventurous measure was associated with being older, having more gay friends, being HIV-positive, and being more sexually active. It was also independently associated with unprotected anal intercourse with casual partners (AOR 1.82; 95 % CI 1.20-2.76; p = 0.005). HIV prevention strategies need to account for the different subcultural groupings in which GBM participate. Measures of engagement with gay subcultures are useful indicators of differential rates of risk behavior and modes of participation in gay community life. Men in more sexually adventurous subcultures are more likely to engage in sexual risk behavior.