This paper describes how a combination of high-resolution numerical modeling, a robust homogenization algorithm, and local pressure observations have been used to understand and reconcile time series of daily, seasonal, and annual peak wind gusts recorded at observing sites in the Cook Strait region of New Zealand. The homogenization algorithm consists of corrections for the relocation of masts, changes in instrumentations, data acquisition and signal processing, surrounding surface roughness, and measurement heights. In addition, a statistical method, penalized maximal F test (PMFT), was used to assess the homogeneity of the wind speed time series and detect and eliminate all remaining, undocumented, artificial (i.e., nonclimatic) breakpoints. A three-dimensional time-dependent computational fluid dynamics (CFD) simulation was carried out using the Gerris model to characterize the turbulence environment at the mast sites and to estimate topographic speedup effects. Trends in magnitudes and frequencies of the homogenized seasonal and annual peak wind gusts are evaluated and presented for the Cook Strait region. The pressure gradients between pairs of stations were used to study the correlation between the gust wind speeds and the pressure field. A high-resolution convection-resolving numerical weather prediction model [the New Zealand Convective-Scale Model (NZCSM)] was employed to aid the interpretation of results and analyze wind trends. The trend in gust speeds is also shown to be consistent with larger-scale NCEP–NCAR reanalysis pressure trends. The homogenization algorithm showed promising results in eliminating the artificial breakpoints and trends. Overall, strong correlations were found between the homogenized gust speeds, the pressure field across the region, and NZCSM predictions. [ABSTRACT FROM AUTHOR]