The Value Iteration Network (VIN) is an end-to-end differentiable architecture that performs value iteration on a latent MDP for planning in reinforcement learning (RL). However, VINs struggle to scale to long-term and large-scale planning tasks, such as navigating a $100\times 100$ maze -- a task which typically requires thousands of planning steps to solve. We observe that this deficiency is due to two issues: the representation capacity of the latent MDP and the planning module's depth. We address these by augmenting the latent MDP with a dynamic transition kernel, dramatically improving its representational capacity, and, to mitigate the vanishing gradient problem, introducing an "adaptive highway loss" that constructs skip connections to improve gradient flow. We evaluate our method on both 2D maze navigation environments and the ViZDoom 3D navigation benchmark. We find that our new method, named Dynamic Transition VIN (DT-VIN), easily scales to 5000 layers and casually solves challenging versions of the above tasks. Altogether, we believe that DT-VIN represents a concrete step forward in performing long-term large-scale planning in RL environments.