Elastomeric poly(dimethylsiloxane) (PDMS) stamps were used for micro-contact printing (μ-CP) to pattern the adsorption of alkanethiolates on surfaces of gold on a scale of submicron. With this printing, organic surfaces patterned with well-defined regions exhibiting different chemical and physical properties have been produced. Au-coated mica substrates were treated with functionalized thiols to produce self-assembled monolayer (SAM) surfaces terminating with Br and OH groups by μ-CP method. Lateral force microscopy (LFM) has been utilized to characterize the adhesive interactions between substrates and probe tips that had been functionalized with SAMs which terminate with Br and COOH groups, respectively. LFM data exhibit that friction force between the probe tip and sample surfaces strongly depends on the functionality of both surfaces. This approach can be served as a method for mapping more complex and chemically heterogeneous surfaces.