The study aims to realize the recycling of the heavier portion of bio-oil produced in pyrolysis to achieve a higher char yield in a two-stage fixed bed. Simultaneously, the influence of condensation temperature in the second-stage reactor on the obtained char yield was probed as well. For further investigation on the physicochemical properties of char samples, ultimate analysis, N-2 adsorption-desorption measurements, Raman spectroscopy, and Fourier-transform infrared spectroscopy analysis were conducted. In addition, the reactivity of char samples in air was determined using a thermogravimetric analyzer. The results suggested that the char samples produced by the recycling of heavy oil resulted in a relatively high yield. Simultaneously, different condensation temperatures of the second layer during pyrolysis had a significant impact on the experimental results: as the temperature increased, the char yield and the O/C molar ratio decreased, whereas the value of I-G/I-ALL increased. Finally, it was found that the increase of condensation temperature in the second layer led to the decline of char reactivity. The dimensionless index (DI) was used to show the physicochemical properties of char, and a linear relationship between the oxidation activity index and DI was achieved, which could be used to predict the char reactivity based on the physicochemical properties for industrial applications.