Since 1976, the Ocala National Forest and surrounding areas have accounted for over 50 percent of all black bear roadkill in Florida. To better understand the dynamics involved with this source of mortality, the Florida Fish and Wildlife Conservation Commission, in partnership with the Florida Department of Transportation and the United States Forest Service, began investigating the movements, habitat use, and home range dynamics of black bears relative to roads in Ocala National Forest. This paper presents the preliminary findings from the first two years of the study and focuses on the characteristics of bear crossings of State Road 40. We captured 94 bears (36F, 58M) and collected more than 3,400 locations from 77 radio-collared individuals. Radio-collared bears crossed State Road 40 a total of 324 times, with both sexes crossing at similar frequencies. Concomitant with telemetry locations, we documented 752 sets of bear tracks along a 17.7-kilometer disced transect adjacent to State Road 40. Bears crossed State Road 40 most frequently during the fall, with other peaks in spring and summer. We compared crossing sites to the available habitat adjacent to State Road 40 and documented road mortality sustained by bears since 1976. Bears crossed in young to medium aged stands of sand/pine scrub at higher frequencies than would be expected by chance. Bears crossed in mature sand/pine scrub and scrub oak stands at lower frequencies than would be expected by chance. The sites at which bears were most often struck by vehicles did not coincide with locations where bears most frequently crossed the road. There seem to be highway design features that may contribute to this phenomenon.