In this paper, we consider the specific problem of word-level language modeling and investigate strategies for regularizing and optimizing LSTM-based models. We propose the weight-dropped LSTM, which uses DropConnect on hidden-to-hidden weights, as a form of recurrent regularization. Further, we introduce NT-ASGD, a non-monotonically triggered (NT) variant of the averaged stochastic gradient method (ASGD), wherein the averaging trigger is determined using a NT condition as opposed to being tuned by the user. Using these and other regularization strategies, our ASGD Weight-Dropped LSTM (AWD-LSTM) achieves state-of-the-art word level perplexities on two data sets: 57.3 on Penn Treebank and 65.8 on WikiText-2. In exploring the effectiveness of a neural cache in conjunction with our proposed model, we achieve an even lower state-of-the-art perplexity of 52.8 on Penn Treebank and 52.0 on WikiText-2. We also explore the viability of the proposed regularization and optimization strategies in the context of the quasi-recurrent neural network (QRNN) and demonstrate comparable performance to the AWD-LSTM counterpart. The code for reproducing the results is open sourced and is available at https://github.com/salesforce/awd-lstm-lm.