The aim of the study is to describe the maternal health burden and perinatal outcomes in triplet pregnancies, and identify the maternal and pregnancy indicators associated with increased perinatal morbidity and mortality. This is a retrospective cohort study of triplet pregnancies from 2007 to 2014. Maternal data were manually collected and assessed until 6 weeks postpartum, and neonatal data were assessed until hospital discharge or death. Eighty-two triplet pregnancies were identified with 246 babies born. Mean gestational age at delivery was 32.3 (standard deviation [SD] ± 3.6) weeks and average birth weight was 1,726 g (SD ± 500). There were 12 perinatal deaths and 25 (10.2%) infants diagnosed with a congenital anomaly. Prior preterm birth and nulliparity had a negative impact on gestational age at delivery (p = 0.016) as compared with prior full-term births. Pregnancy complications (preeclampsia or hypertensive disorders [46.3%], gestational diabetes [28%], postpartum hemorrhage [9.8%], and blood transfusions [8.5%]) also impacted gestational age at delivery (33.0 vs. 34.0 weeks, p = 0.031). Spontaneous conception, chorionicity, and maternal medical problems did not have an impact on median gestational age. Nulliparity and presence of pregnancy complications are pertinent to triplet outcomes. This study provides valuable information for anticipatory guidance and preconception counseling to patients considering artificial reproductive technology.