Bioretention systems are one example of green stormwater infrastructure that may mitigate the hydrologic impact of stormwater runoff. To improve water retention while maintaining rapid stormwater infiltration, conventional bioretention soil media (BSM) might be augmented with biochar. Biochar may improve the BSM's structure by increasing soil aggregation, which might improve water retention and increase stormwater infiltration while also improving root growth. Pots with BSMs representing high and moderate sand content media were amended with a wood-derived biochar, planted with switchgrass, and subjected to weekly storms for 20 weeks, followed by a 10-week drought. In the high sand content medium (NC mix), biochar amendment increased hydraulic conductivity (Ksat), and this effect increased with time. At 0 weeks, 2% and 4% (w/w) biochar increased Ksat by 4 ± 2% and 10 ± 4%, respectively, while at 30 weeks the increase was 30 ± 10 and 70 ± 20%, respectively, above biochar-free media. Similar improvements were seen in plant available water (PAW) in NC mix. However, minimal improvements in Ksat and PAW from biochar amendment were found in the moderate sand content BSM that contained compost and mulch (DE mix). Where biochar promoted Ksat, this was correlated with increased water-stable aggregate size (r = 0.86), fine root volume (r = 0.88), and below ground biomass (r = 0.83). Important factors affecting Ksat and aggregation in the NC mix were biochar's influence on organo-mineral association, fungal hyphae length, and plant roots. Wood-derived biochar amendment to BSM may obviate the need for compost/mulch since biochar has similar effects on improving BSM hydrology and root growth without the risk of undesired nutrient leaching.