This chapter explores how queer people experience residential and entertainment space in Cambridge, MA, one of the most progressive cities in its region. Queer people who participated in in-depth interviews were asked about the spaces they feel the most and least comfortable being queer. Queering spaces are often less enclosed than queer spaces, that are having more porous transitions between the sidewalk and the establishment such as outdoor seating or glass facades. Many queering spaces are coffee shops or districts that are physically differentiated in some manner, either by being semi-enclosed or by being architecturally distinct. Several interviewees recalled Paradise, a long-standing bar/sex club, but none had been there in years. They described Paradise as a formerly straight neighborhood bar that had found its current niche as queer space in the 1990s when other queer bars were dying out. The monastery has a weekly worship space with a garden that is open to the public.