Seasonal reconstructions of streamflow are valuable because they provide water planners, policy makers, and stakeholders with information on the range and variability of water resources before the observational period. In this study, we used streamflow data from five gages near the Alabama-Florida border and centuries-long tree-ring chronologies to create and analyze seasonal flow reconstructions. Prescreening methods included correlation and temporal stability analysis of predictors to ensure practical and reliable reconstructions. Seasonal correlation analysis revealed that several regional tree-ring chronologies were significantly correlated (p ≤ 0.05) with March–October streamflow, and stepwise linear regression was used to create the reconstructions. Reconstructions spanned 1203–1985, 1652–1983, 1725–1993, 1867–2011, and 1238–1985 for the Choctawhatchee, Conecuh, Escambia, Perdido, and Pascagoula Rivers, respectively, all of which were statistically skillful (R2 ≥ 0.50). The reconstructions were statistically validated using the following parameters: R2 predicted validation, the sign test, the variance inflation factor (VIF), and the Durbin–Watson (D–W) statistic. The long-term streamflow variability was analyzed for the Choctawhatchee, Conecuh, Escambia, and Perdido Rivers, and the recent (2000s) drought was identified as being the most severe in the instrumental record. The 2000s drought was also identified as being one of the most severe droughts throughout the entire reconstructed paleo-record developed for all five rivers. This information is vital for the consideration of present and future conditions within the system.