Pine Hollow Farms, an 800-cow dairy in central New York, performed a small, randomized trial in the summer of 2006 to compare pregnant heifers managed on pasture versus those kept in free-stall housing. Forty-eight pregnant heifers were targeted based on freshening date to allow for five months of either pasture or in-door loose housing management and then 30 days together in the pre-fresh group. The heifers were weighed in the spring and assigned randomly to a treatment group by sending every other heifer to either pasture or confinement. Until that time both groups were managed indentically in terms of weaning, housing, diet, breeding, deworming, vaccinations, and hoof trimming. Dairy Comp 305 was used to record and retrieve peripartum diseases (displaced abomasa, metritis, ketosis, retained placentas), lameness, mastitis, culling, milk production, calving to conception interval, and number of times bred. This paper discusses the differences revealed through this trial, the pros and cons of both management systems, as well as a proposed partial budget.