Patterns of overwash deposition observed within back-barrier sediment archives can indicate past changes in tropical cyclone activity; however, it is necessary to evaluate the significance of observed trends in the context of the full range of variability under modern climate conditions. Here we present a method for assessing the statistical significance of patterns observed within a sedimentary hurricane-overwash reconstruction. To alleviate restrictions associated with the limited number of historical hurricanes affecting a specific site, we apply a recently published technique for generating a large number of synthetic storms using a coupled ocean-atmosphere hurricane model set to simulate modern climatology. Thousands of overwash records are generated for a site using a random draw of these synthetic hurricanes, a prescribed threshold for overwash, and a specified temporal resolution based on sedimentation rates observed at a particular site. As a test case we apply this Monte Carlo technique to a hurricane-induced overwash reconstruction developed from Laguna Playa Grande (LPG), a coastal lagoon located on the island of Vieques, Puerto Rico in the northeastern Caribbean. Apparent overwash rates in the LPG overwash record are observed to be four times lower between 2500 and 1000 years B.P. when compared to apparent overwash rates during the last 300 years. However, probability distributions based on Monte Carlo simulations indicate that as much as 65% of this drop can be explained by a reduction in the temporal resolution for older sediments due to a decrease in sedimentation rates. Periods of no apparent overwash activity at LPG between 2500 and 3600 years B.P. and 500–1000 years B.P. are exceptionally long and are unlikely to occur (above 99% confidence) under the current climate conditions. In addition, breaks in activity are difficult to produce even when the hurricane model is forced to a constant El Niño state. Results from this study continue to support the interpretation that the western North Atlantic has exhibited significant changes in hurricane climatology over the last 5500 years.