In this paper, three different flash floods episodes were analyzed, which occurred in October 2006, February 2010, and June 2018 in the Chalkidiki peninsula (North Greece). The Soil Conservation Service (SCS) model and a revised assessment of the CN parameter were applied to estimate the flood hydrographs, and Hydrologic Engineering Center's-River Analysis System (HEC-RAS) software was used for the flood simulations. Initially, hydrological and hydraulic models were calibrated at Vatonias watershed (240.90 km 2 , North Greece), where three rain gauges and one water level station are located. Vatonias is located very close to the Stavros ungauged watersheds and presents similar geomorphology and land use conditions. The effectiveness and accuracy of the methodology were validated using post-flash-flood measurements. The root mean square error goodness of fit was used to compare the observed and simulated flood depths. Critical success index was calculated for the assessment of the accuracy of observed and modeled flooded areas. The results showed that the dense forest vegetation was not capable of preventing the flash flood generation or reducing the peak discharge, especially in small watersheds characterized by short concentration times. The main cause of flash flood generation was the human interference that influenced the hydraulic characteristics of streams and floodplains. The revised assessment of the CN parameter enhanced the estimation and spatial distribution of CN over the entire watershed. The results revealed that the proposed methodology could be a very useful tool to researchers and policy makers for flood risk assessment of higher accuracy and effectiveness in ungauged Mediterranean watersheds.Hydrology 2020, 7, 12 2 of 24 settlements with the tolerance of the state have led to the gradual trespass of torrents, the reduction of streambed width, and in some cases to their complete disappearance. Under these circumstances, the hydraulic characteristics of streams and floodplains have been altered dramatically and have resulted in the intensification of the flood phenomena [10][11][12][13]. The protective role of forests from flash flood generation is questionable, and according to previous research studies is very limited, indicating that forests have negligible effects on the reduction of peak discharge during extreme rainfall events [10,12,14,15].Over the past years, considerable efforts have been made to estimate flood risk and simulate flood events, using hydrological and hydraulic models [16][17][18][19][20][21][22][23]. However, these models require the existence of large time series and reliable stream flow and rainfall data, which in most Mediterranean areas are unfortunately not available, especially for medium and small watersheds. To overcome these practical difficulties, post-flash-flood measurements could be considered very useful for the evaluation of the hydrological and hydraulic models by reproducing the flood events and comparing the observed flooded area and flood depth with the si...