Despite generally improved societal attitudes toward sexual minority individuals, gay men continue to experience injustices and stigma related to their sexual minority identity, with harmful consequences for their health and well-being. However, sexual minority status can also be a source of strength or support through gay community connection and access to community resources. This dissertation project aimed to further our understanding of gay community connection and the ways in which it may improve psychological well-being among gay men in two complementary studies. The first study quantitatively examined different aspects of gay community connection (i.e., quality of perceived connection, frequency of enactments, or social network representation) and how they could differentially predict depressive symptoms and/or differentially moderate the association between sexual stigma and depressive symptoms in a sample of young sexual minority men. Results indicated a positive association between community identification and community enactment among young sexual minority men. Different forms of gay community connection were not associated with depressive symptomatology and did not buffer the effects of sexual stigma on depressive symptoms. The second study used a qualitative approach to provide an in-depth understanding of gay community connection and the experiences of gay men attending or residing at a gay campground in the rural South. Results revealed eight primary themes related to the participants’ experiences of the campground, including: general community, social, & interpersonal connections; gay-specific community, social, & interpersonal connections; lifestyle; environment; feelings of isolation & loneliness; well-being; representation & acceptance; and external stigma. Taken together, results from these two studies highlight contemporary experiences of gay community connection and suggest various ways in which this connection is experienced. These studies highlight the need to take a more nuanced perspective to understand the many forms (e.g., connectedness, enactment, and social network) and available venues (e.g., gay bar, gay campground) available to gay men today. Findings from this dissertation can inform future work examining gay community connection, its associations with stress and well-being, and the factors that influence decisions and access to gay community connection.