Recent research has examined how gay and bisexual men experience and navigate the variations in sexual minority stigma that exist across geographic contexts, with implications for their health. We extend this literature on stigma, mobility, and health by considering the unique and understudied setting of the small city. Drawing on semi-structured interviews (n = 29) conducted in two small US cities (New Haven and Hartford), we find that these small cities serve as both destinations and points of departure for gay and bisexual men in the context of stigma. New Haven and Hartford attracted gay and bisexual men from surrounding suburbs where sexual minority stigma was more prevalent and where there were fewer spaces and opportunities for gay life. Conversely, participants noted that these small cities did not contain the same identity affirming communities as urban gay enclaves, thus motivating movement from small cities to larger ones. Our data suggest these forms of mobility may mitigate stigma, but may also produce sexual health risks, thus drawing attention to small cities as uniquely important sites for HIV prevention. Furthermore, our analysis contributes to an understanding of how place, stigma and mobility can intersect to generate spatially distinct experiences of stigmatised identities and related health consequences.