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Agriculture can be a contributor of pollutants, including pesticides and excess sediment, to aquatic environments. However, side-inlet vegetated filter strips (VFSs), which are planted around the upstream side of culverts draining agricultural fields, may provide reductions in pesticide and sediment losses from agricultural fields, and have the additional benefit of removing less land from production than traditional VFS. In this study, reductions of runoff, the soluble pesticide acetochlor, and total suspended solids were estimated using a paired watershed field study and coupled PRZM/VFSMOD modeling for two treatment watersheds with source to buffer area ratios (SBAR) of 80:1 (SI-A) and 481:1 (SI-B). Based on the paired watershed ANCOVA analysis, runoff and acetochlor load reductions were significant following the implementation of a VFS at SIA but not SI-B, indicating the potential for side-inlet VFS to reduce runoff and acetochlor load from a watershed with an area ratio of 80:1 but not a higher ratio of 481:1. VFSMOD simulations were consistent with the results of the paired watershed monitoring study, where simulated reductions of runoff, acetochlor loads, and TSS loads were substantially lower for SI-B than SI-A. VFSMOD simulations of SI-B with the SBAR ratio observed at SI-A (80:1) also show that VFSMOD can be used to capture variability in effectiveness of VFS based on multiple factors including SBAR. While this study focused on the effectiveness of side-inlet VFSs at the field scale, broader adoption of properly sized side-inlet VFSs could improve surface water quality at the watershed or larger scales. Additionally, modeling at the watershed scale could aid in locating, sizing, and assessing the impacts of side-inlet VFSs at this larger scale., Competing Interests: Declaration of competing interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Meghan Arpino, John Hanzas, Jody Stryker, Michael Winchell, Don Meals reports financial support was provided by Acetochlor Registration Partnership, which consists of Bayer US Crop Science Division and Corteva Agriscience., (Copyright © 2023 The Authors. Published by Elsevier B.V. All rights reserved.)