State-of-the-art classification and regression models are often not well calibrated, and cannot reliably provide uncertainty estimates, limiting their utility in safety-critical applications such as clinical decision-making. While recent work has focused on calibration of classifiers, there is almost no work in NLP on calibration in a regression setting. In this paper, we quantify the calibration of pre- trained language models for text regression, both intrinsically and extrinsically. We further apply uncertainty estimates to augment training data in low-resource domains. Our experiments on three regression tasks in both self-training and active-learning settings show that uncertainty estimation can be used to increase overall performance and enhance model generalization.