Denning behavior has long remained the least observed aspect of bear behavior. During 2010–2013, we used webcams, microphones, the internet, and 14,602 h of archived video to document the denning behaviors of two adult wild black bears (Ursus americanus) as they gave birth and cared for four litters through six winters in northeastern Minnesota. Observations included types of dens, labor, pre-parturient genital swelling, birthing positions, post-partum vocalizations, mothers removing amniotic tissues and warming newborn cubs in sub-freezing temperatures, frequency of nursing, cubs establishing nipple order, yearlings suckling, the ingestion of snow and icicles, the ingestion of foot pads, urination and defecation in latrine areas, toilet-licking, eye opening, reciprocal tongue-licking, play, rapid eye movement (REM) sleep and possible dreaming, and reactions to wildlife intruders. The use of this new method for observing natural bear dens allowed the identification of many behaviors undescribed for any species of wild bear in dens. We also discuss the need for future studies and how the depth and duration of black bear hibernation varies with body condition and geographic region.