The article presents the results of measurements regarding the impact of the MHT9002HV tracked harvester on surface deformations and changing the physical parameters of the soil of three operational trails. The measurements were made in the terrain with a longitudinal slope of up to 14.9° (33.2%) and a transverse slope of up to 8.8° (17.9%). Spruce deadwood trees in mountain forest habitats were harvested. Static Eijkelkamp Penetrologger 0615SA and dynamic own design penetrometer were used to measure penetration resistance, soil samples were taken to determine bulk density, moisture content, and ground deformations on the trails were measured with a laser profilometer. A statistically significant increase in soil penetration resistance measured with penetrometers occurred for trails in the left rut at a depth of 16–20 cm. The change in the bulk density and moisture content proved statistically insignificant. The maximum ground deformation on the trails reached an average of 5.9 cm. The selection of a machine with low unit pressures (33 kPa), under the given favorable atmospheric conditions (there was a high temperature reaching 35 °C), with low soil moisture, protective organic layer of high thickness, and post-limbing residues, was optimal. The comparison of the results of the compactness measurements made with different penetrometers shows that the values obtained for the static penetrometer 0615SA are lower than those of the dynamic penetrometer of our own design. This is due to the lack of registration of high compactness in the memory of the 0615SA device. In the case of the impact penetrometer measurement, this problem does not occur, however, the presented solution does not allow performing a large number of measurements, and data processing in the case of such a simple solution is tedious. There is a need to develop a new penetrometer useful for determining soil compaction under similar difficult measurement conditions.