Modelling wind speeds in urban areas have many applications e.g. in relation to assessment of wind energy, modelling air pollution, and building design and engineering. Models for extrapolating the urban wind speed exist, but little attention has been paid to the influence of the upwind terrain and the foundations for the extrapolation schemes. To analyse the influence of the upwind terrain and the foundations for the extrapolation of the urban wind speed, measurements from six urban and non-urban stations were explored, and a model for the urban wind speed with and without upwind influence was developed and validated. The agreement between the wind directions at the stations is found to be good, and the influence of atmospheric stability, horizontal temperature gradients, land-sea breeze, temperature, global radiation and Monin-Obukhov Length is found to be small, although future work should explore if this is valid for other urban areas. Moreover, the model is found to perform reasonably well, but the upwind influence is overestimated. Areas of model improvement are thus identified. The upwind terrain thus influences the modelling of the urban wind speed to a large extent, and the fundamental assumptions for the extrapolation scheme are fulfilled for this specific case.