In this paper we study the $C^1$-regularity of solutions of one-dimensional variational obstacle problems in $W^{1,1}$ when the obstacles are $C^{1,\sigma}$ and the Lagrangian is locally H\"older continuous and globally elliptic. In this framework, we prove that the solutions of one-dimensional variational obstacle problems are $C^1$ for all boundary data if and only if the value function is Lipschitz continuous at all boundary data.