We analyzed the reproductive success of eastern bluebirds (Sialia sialis) nesting in apple orchards and non‐orchard nest‐boxes in southern Ontario, Canada, from 1988 to 2018. Using data from 2397 nest‐boxes monitored at 20 orchard sites and 52 non‐orchard sites, we first modeled phenological parameters typically linked to climate change across both site types. We found that the first egg of each brood was laid significantly earlier in the season each year over our 31‐year study. Clutch initiation occurred 4 days earlier in the spring in 2018 compared to 1988. Average clutch size in the first or second brood did not change significantly during our 31‐year study; however, clutches were significantly smaller in orchards compared to non‐orchards (0.10 ± 0.03 fewer eggs between sites). Nests built in orchards were also at 6.1‐fold greater risk of parasitism and 2.1‐fold greater risk of depredation than nests in non‐orchards. After accounting for depredation and nest parasitism, hatching success was still significantly lower in orchards than in non‐orchards. Overall, hatching success was 4%–5% lower in orchards. The probability of successfully fledging did not differ significantly between site types. In 2012, a ban on use of the organophosphate insecticide azinphos‐methyl in orchards was enacted in Canada. We did not find a difference in hatching or fledging success in orchards after the ban. In our assessment of available data, we conclude that any pesticide effect on hatching success of eastern bluebirds in sprayed orchards is most likely the consequence of long‐term exposure to dichlorodiphenyltrichloroethane (DDT) compounds in orchard soils and bioaccumulation in eggs rather than pesticides in use since regulation of DDT in the 1970s. Environ Toxicol Chem 2021;40:3369–3378. © 2021 Her Majesty the Queen in Right of Canada. Environmental Toxicology and Chemistry published by Wiley Periodicals LLC on behalf of SETAC. Reproduced with the permission of the Minister of Environment and Climate Change Canada.