Anecdotal information indicates that streams in the Mid-Atlantic region of the United States experience more extreme flood events than might be expected. This leads to the question of whether this is an unfounded perception or if these extreme events are actually occurring more than should be expected. If the latter is true, is this due solely to randomness, or alternately to characteristics that make certain watersheds more prone to repeated events that may be defined as 100-year or greater floods? These questions are investigated through analysis of flood events based on standard flood frequency analysis. 100-year streamflow rates for stream gages were estimated using Bulletin 17B flood frequency analysis methods, and the probability of the annual peak flow record for each gage was calculated. These probabilities were compared to a set of synthetic probabilities to evaluate their distribution. This comparison indicates that for the Mid-Atlantic region as a whole, the Bulletin 17B method does not systematically over or underestimate flood frequency. A Random Forest model of probability of actual flood record (PAFR) versus watershed and stream gage characteristics was developed and used to understand if certain characteristics are associated with PAFR. This analysis indicated that unexpected numbers of large flood events in a stream gage period of record can be attributed primarily to randomness, but there is some correlation with watershed and gage characteristics including weighted skew, drainage area, and mean annual peak discharge. The results indicate that watersheds with high values of these characteristics may warrant advanced flood frequency methods.