Interactions between a hydrophobic probe particle and surfaces with nanoscopic surface features have been investigated. Such surfaces were prepared by polishing or by spin-coating of nanoparticles. The surface topography was characterized by AFM, using the methods of high-resolution imaging, low-resolution imaging using the probe particle, and by the rolling ball method. The polished surfaces display sharp nanoscopic peaks and hardly any crevices. In contrast, the spin-coated surfaces can be characterized as nanostructured, due to the high density of nanoparticles that on a short length scale provides a regular pattern of crevices and hills. On all surfaces a larger waviness is also distinguished. In all cases the dominant force at short separations was found to be a capillary attraction due to the formation of an air/vapour condensate. Our data show that the large-scale waviness of the surface does not signiﬁcantly inﬂuence the range and magnitude of the capillary attraction, but large local variations in these quantities are found. The large variation in adhesion force corresponds to a small variation in local contact angle of the capillary condensate at the surfaces. The report discusses how the nature of the surface topographical features inﬂuences the capillary attraction by inﬂuencing the local contact angle and by pinning of the three phase contact line. The effect is clearly dependent on whether the surface features exist in the form of crevices or as extending ridges.