In this paper we study the moduli space of the tropicalizations of Riemann surfaces. We first tropicalize a smooth pointed Riemann surface by a graph defined by its (hyperbolic) pair of pants decomposition. Then we can construct the moduli space of tropicalizations based on a fixed regular tropicalization, and compactify it by adding strata parametrizing weighted contractions. We show that this compact moduli space is also Hausdorff. In the end, we compare this moduli space with the moduli space of Riemann surfaces, establishing a partial order-preserving correspondence between the stratifications of these two moduli spaces.