Cows unable to cope with the challenges of calving often succumb to disease, negatively affecting their welfare. This may be improved by accommodating the cows’ preferences at calving. The objective was to determine the effects of parity, season, and group size on dairy cows and heifers’ preference for calving location when group housed and provided free access to pasture. This study was implemented using an observational study design. Multiparous Holstein cows (n = 33) and nulliparous Holstein heifers (n = 32) were dynamically enrolled −21 d before their expected calving date and removed on the day of calving. Cows had continuous access to a bedded-pack barn (area 1; 167.4 m²), open pasture (area 2; 1.82 ha), and an area of natural forage cover (i.e., trees and tall grasses; area 3; 0.24 ha). Video data were used to determine calving location. Cows calved from August to December 2016. Season was categorized as summer (August 6 to September 21), fall (September 22 to December 20) and winter (December 21 to December 28). For each cow, mean daily group size was calculated over the days she was enrolled, including at calving. Multinomial logistic regression (SAS 9.4) was used to test if factors were associated with the probability of calving in the 3 designated areas of the environment, and model selection was performed by backward manual elimination. Twenty-five calvings (38%) occurred in the barn, 17 calvings (26%) occurred on open pasture, and 23 calvings (35%) occurred in the area of natural forage cover. Parity was associated with the location of calving (P = 0.02); heifers were more likely to calve in the natural forage area compared with the barn (OR = 5.88; 95% CI = 1.69, 20.42). However, heifers and cows were equally as likely to calve in open pasture or the barn (OR = 2.89; 95% CI = 0.8, 10.53). Season, group size at calving, and mean daily group size were not associated with calving location preference (P > 0.25). These results suggest parity plays a role in preference for calving location when group housed. Calving areas that accommodate both heifers and cows’ environmental preferences for calving when grouped may improve calving outcomes.