Lunar exploration and infrastructure development near the Moon's south pole, and at other future lunar settlements, demand a detailed understanding of the geotechnical properties, structure, composition, and stratigraphy of the near-surface lunar regolith. Long term exploration and development activities will require the use of regolith as a construction material for multiple structures, and as unrefined material for resource extraction during in situ resource utilization (ISRU) activities. Upcoming robotic and human exploration will be concentrated near the lunar south pole, which has a dominantly feldspathic composition typical of the lunar highlands. Past missions to lunar highlands terrain (Apollo 16, Luna 20) provide valuable “ground truth” data regarding the geomechanical properties of highlands regolith that serve as a guide for future exploration at the lunar south pole. Lunar highlands simulant LHS-1 has well-characterized geotechnical properties and is an appropriate analogue for highlands lunar regolith in terrestrial engineering studies. Cone penetrometer testing (CPT) measurements of LHS-1 reveal a strong exponential correlation between the G slope parameter and bulk density, which allows information to be obtained regarding the density profile of simulated regolith columns directly from CPT stress versus penetration curves. We show that LHS-1 can be used to replicate the near-surface regolith stratigraphy at the Apollo 16 highland landing region in Earth-based laboratories. The ultimate CPT penetration resistance measured in the laboratory under terrestrial gravity is not directly comparable to that measured under lunar gravity, and here we derive an average reduction factor of Rf = 0.29 to scale penetration resistance values to those measured in situ on the lunar surface. Geotechnical measurements of other lunar simulants combined with experiments similar to those described herein, tailored to the terrain type of interest, will provide crucial information to guide future regolith excavation, construction, and ISRU activities on the lunar surface.