Background: Fenway Health (FH) is the largest ambulatory facility caring for men who have sex with men (MSM) in New England; of ~6,000 MSM clients, 1,200 are HIV-infected. Objectives: To describe changes in STD prevalence among MSM at FH, 1997-2008. Methods: Electronic medical records over the last 12 years were reviewed; statistical analyses, including Chi-square tests, and tests for trend, were performed, comparing infection rates over time and by demographics. Results: In 2008, 3,493 MSM at FH were screened for one or more STD. They had a mean age of 39 years (SD=11), the majority were Caucasian (73%), 30% were HIV-infected, and 62% had private insurance. In 1997, only 38 cases of gonorrhea and 2 of syphilis were diagnosed at FH, but by 2008, 75 cases of gonorrhea (45 urethral, 30 rectal) and 156 new syphilis infections were detected (p<.0001). In 2004, 51 chlamydia infections were diagnosed, compared to 80 cases in 2008 (p<.0001). Men with STDs tended to be Caucasian (74%; p<.0001) and HIV-infected (53%; p<.0001), but had wide age distribution, with 26% <30 y.o. and 49% >40 y.o. In 1997, 67% of MSM with a new STD lived within the 3 zip codes adjacent to FH, but by 2008, 82% of the men came from noncontiguous areas (p<.0001). Since 2000, half of the men diagnosed with syphilis were HIV-infected, and in 2008, 71% were HIV-infected (p<.001). Conclusions: STDs have been increasingly detected in MSM seen at FH with wider geographic representation, consistent with regional spread. Syphilis rates have increased considerably, particularly among HIV-infected MSM, but rises have also been seen with other bacterial STDs. Intensified screening, community education and prevention programs are warranted. Implications for Programs, Policy, and/or Research: The increase in STD, namely syphilis, among HIV-infected MSM underscores the need for focused prevention interventions for patients in care settings.