Significant uncertainties remain regarding the field assessment of the peak shear strength of rock joints. These uncertainties mainly originate from the lack of a verified methodology that would permit prediction of rock joints’ peak shear strength accounting for their surface area, while using information available from smaller samples. This paper investigates a methodology that uses objective observations of the 3D roughness and joint aperture from drill cores to predict the peak shear strength of large natural, unfilled rock joints in the field. The presented methodology has been tested in the laboratory on two natural, unfilled rock joint samples of granite. The joint surface area of the tested samples was of approximately 500 × 300 mm. In this study, the drill cores utilised to predict the peak shear strength of the rock joint samples are simulated based on a subdivision of their digitised surfaces obtained through high-resolution laser scanning. The peak shear strength of the tested samples based on the digitised surfaces of the simulated drill cores is predicted by applying a peak shear strength criterion that accounts for 3D roughness, matedness, and specimen size. The results of the performed analysis and laboratory experiments show that data from the simulated drill cores contain the necessary information to predict the peak shear strength of the tested rock joint samples. The main benefit of this approach is that it may enable the prediction of the peak shear strength in the field under conditions of difficult access.