This study investigated the impact of irrigation sources (pond, stream, and well) in high tunnel-dripline systems on the dissemination and persistence of foodborne pathogens (Escherichia coli O157, Listeria monocytogenes, Campylobacter spp., Salmonella spp., and the ‘big six’ Shiga toxin-producing E. coli [STEC]) in small specialty crop farms (SSCFs). Ten SSCF-growing fresh tomatoes using high tunnel-dripline systems were sampled between January and November 2022. Selective enrichment combined with PCR was used to detect the selected foodborne pathogens in the irrigation water (n = 240), soil (n = 240), and tomato fruits (n = 120). Overall, surface-originated water sources (streams and ponds) having potential contact with farm animals or wildlife harbored higher pathogen burden (cumulative prevalence of all the pathogens) compared to subsurface water source (well and underground spring water). STEC O26, O45, and O103 were detected at high frequency (up to 88% per SSCF per time point) in the water source and associated dripline irrigation system of 4/6 SSCFs using stream and pond water. Other foodborne pathogens (especially, L. monocytogenes) were detected in 6/10 SSCFs, but at low frequency (<25% per SSCF per time point). The prevalence of foodborne pathogens in the 10 SSCFs over time was positively correlated with the length of high tunnel and planting date (r2 = 0.93 and 0.79, respectively; P < 0.006). Our study highlighted that dripline irrigation systems may allow the long-distance transport of foodborne pathogens from the contaminated water source to the field. Risk assessment and mitigation measures should be implemented to assure the quality of the water source used for irrigation in SSCF.