BACKGROUND: We aimed to identify the 2001-2013 incidence trend, and characteristics associated with adolescent pregnancies reported by 20-24-year-old women. METHODS: A retrospective analysis of the Cuatro Santos Northern Nicaragua Health and Demographic Surveillance 2004-2014 data on women aged 15-19 and 20-24. To calculate adolescent birth and pregnancy rates, we used the first live birth at ages 10-14 and 15-19 years reported by women aged 15-19 and 20-24 years, respectively, along with estimates of annual incidence rates reported by women aged 20-24 years. We conducted conditional inference tree analyses using 52 variables to identify characteristics associated with adolescent pregnancies. RESULTS: The number of first live births reported by women aged 20-24 years was 361 during the study period. Adolescent pregnancies and live births decreased from 2004 to 2009 and thereafter increased up to 2014. The adolescent pregnancy incidence (persons-years) trend dropped from 2001 (75.1 per 1000) to 2007 (27.2 per 1000), followed by a steep upward trend from 2007 to 2008 (19.1 per 1000) that increased in 2013 (26.5 per 1000). Associated factors with adolescent pregnancy were living in low-education households, where most adults in the household were working, and high proportion of adolescent pregnancies in the local community. Wealth was not linked to teenage pregnancies. CONCLUSIONS: Interventions to prevent adolescent pregnancy are imperative and must bear into account the context that influences the culture of early motherhood and lead to socioeconomic and health gains in resource-poor settings.