Introduction: Menstruation is a normal biological process that girls and women experience for the duration of their reproductive years. Normal menstrual cycles during adolescence indicate good current and future reproductive health and general well-being. Dysmenorrhea is the most common menstruation disorder that can be debilitating. This study aims to assess menstruation characteristics among adolescent girls living in Palestinian Refugee Camps in the West Bank of the occupied Palestinian territory and Jordan, estimate dysmenorrhea levels, and assess its associated factors. Methods: A household survey of 15 to 18-year-old adolescent girls was conducted between June and September 2019. Trained field workers collected data on general menstrual characteristics and dysmenorrhea level using the Working ability, Location, Intensity, Days of pain Dysmenorrhea scale (WaLIDD), in addition to demographic, socioeconomic, and health characteristics. The link between dysmenorrhea and other participant characteristics was assessed using a linear regression model. Results: 2737 girls participated in the study. The mean age and mean age-at-menarche were 16.8±1.1 and 13.1±1.2 respectively. Mean bleeding duration was 5.3±1.5 days, and the average cycle length was 28.1±6.2 days. Around 6% reported heavy menstrual bleeding. High dysmenorrhea levels were reported (96%), with 41% reporting severe symptoms. Higher dysmenorrhea levels were associated with older age, earlier age-at-menarche, longer period durations, and heavier menstrual flow, in addition to skipping breakfast regularly and limited physical activity patterns. Conclusions: The study reveals regular menstrual patterns in terms of length, duration, and intensity of bleeding, as well as an age-at-menarche that is slightly higher than the global average. Furthermore, it reflects on an alarmingly high prevalence of dysmenorrhea among participants that tends to vary with different population characteristics. This research calls for collaborative responsibilities and efforts to assist adolescent girls with menstrual health issues, such as dysmenorrhea and irregular periods, so that effective recommendations and actions can be achieved.