This study examined factors associated with tobacco-free policies and tobacco cessation in schools serving children in grades 6 to 12 in a tobacco-growing state using a cross-sectional telephone survey of school administrators from public and private middle and high schools (N = 691), representing 117 of the 120 Kentucky counties. Trained health department staff contacted 1028 schools; 691 (67%) participated in a phone survey, which lasted an average of 19 minutes. Variables of interest were indoor and outdoor smoking policies, fund-raising in Bingo halls, provision of cessation and prevention programs, owning or leasing a tobacco base, if the school received money from tobacco companies, type of school (public vs private), and school setting (urban vs rural). Only 20% of Kentucky schools reported comprehensive tobacco-free policies. Urban area schools were nearly twice as likely to have a tobacco-free campus than rural schools. Schools that did fund-raising in smoky Bingo halls were 30% less likely to have tobacco-free school policies. While few schools had a tobacco affiliation, those that received money from tobacco companies or grew tobacco were nearly 3 times as likely to provide cessation resources, compared to schools without tobacco affiliation. Rural schools were less likely to be tobacco free and provide cessation services. School-related, off-campus, extracurricular events might be considered as an element of tobacco-free school policy. Schools with tobacco affiliation may provide more cessation resources due to the increased prevalence of tobacco use in these areas.