Let $H$ be a graph. The generalized outerplanar Turán number of $H$, denoted by $f_{\mathcal{OP}}(n,H)$, is the maximum number of copies of $H$ in an $n$-vertex outerplanar graph. Let $P_k$ be the path on $k$ vertices. In this paper we give an exact value of $f_{\mathcal{OP}}(n,P_4)$ and a best asymptotic value of $f_{\mathcal{OP}}(n,P_5)$. Moreover, we characterize all outerplanar graphs containing $f_{\mathcal{OP}}(n,P_4)$ copies of $P_4$.