The temperature of pine rosin softening point was studied to better understand the phenomenon of resin exudation on the surface of pine boards. This problem may decrease strongly the aesthetical performance of wood used outside and is an important concern for the industry. To perform a reliable measurement of rosin properties with a small amount of sample, differential scanning calorimetry (DSC) and thermo mechanical analysis (TMA) techniques were investigated and the results compared. DSC curves on industrial rosin and acetone rosin extractives from maritime pine show a behavior similar to a glass transition in polymers. TMA measurements carried out on the same industrial rosin showed that the softening point is in the midpoint of the transition phase observed by DSC. The softening point temperature is about 45 °C for industrial rosin and about 50 °C for rosin extractives from maritime pine boards. These values are significantly lower than those usually found on other rosins measured by the ASTM E28-14 standard using the ring-and-ball method. When using heat treatment, it was observed for the first time that the thermal history of the sample can change its softening point temperature. With these results, it could be possible to develop a new strategy to reduce rosin exudation for exterior wood siding.