Background: Asthma and hay fever have been found to be both positively and negatively associated with farming lifestyles in adulthood. Lack of congruency may depend upon early life exposure. Objective: To assess the importance of different periods of farm residency for asthma and hay fever in an adult Canadian population. Methods: We conducted a questionnaire survey in rural Saskatchewan, Canada. We assessed a history of asthma and hay fever with five categories of farm residency that were mutually exclusive: first year of life only, currently living on a farm, both first year of life and currently living on a farm, other farm living, and no farm living. Generalized estimating equations were used to adjust for clustering effects of adults within households. Results: Of the 7148 responding, 30.6% had an early farm living experience only, 34.4% had both early and current farm living experiences, while 17.4% had never lived on a farm. The overall prevalence of ever asthma and hay fever was 8.6% and 12.3%, respectively, and was higher in women. Sex modified the associations between ever asthma and hay fever with farm residency variables whereby women had a decreased risk for both asthma [adjusted odds ratio (ORadj): 0.67, 95% confidence interval (CI):0.47–0.96] and hay fever (ORadj: 0.60, 95% CI: 0.44–0.83) with an early farm exposure only. Men currently living on a farm without an early farm exposure had an increased risk for ever asthma (ORadj: 1.82, 95% CI: 1.02–3.24). Conclusion: Farm residency in the first year of life shows a protective effect for adult asthma and hay fever that appears to differ by sex.