Achilles tendon injuries are treated with progressive weight bearing to promote tendon healing and restore function. Patient rehabilitation progression are typically studied in controlled, lab settings and do not represent the long-term loading experienced during daily living. The purpose of this study is to develop a wearable paradigm to accurately monitor Achilles tendon loading and walking speed using low-cost sensors that reduce subject burden. Ten healthy adults walked in an immobilizing boot under various heel wedge conditions (30°, 5°, 0°) and walking speeds. Three-dimensional motion capture, ground reaction force, and 6-axis inertial measurement unit (IMU) signals were collected per trial. We used Least Absolute Shrinkage and Selection Operator (LASSO) regression to predict peak Achilles tendon load and walking speed. The effects of using only accelerometer data, different sampling frequency, and multiple sensors to train the model were also explored. Walking speed models outperformed (mean absolute percentage error (MAPE): 8.41 ± 4.08%) tendon load models (MAPE: 33.93 ± 23.9%). Models trained with subject-specific data performed significantly better than generalized models. For example, our personalized model that was trained with only subject-specific data predicted tendon load with a 11.5 ± 4.41% MAPE and walking speed with a 4.50 ± 0.91% MAPE. Removing gyroscope channels, decreasing sampling frequency, and using combinations of sensors had inconsequential effects on models performance (changes in MAPE < 6.09%). We developed a simple monitoring paradigm that uses LASSO regression and wearable sensors to accurately predict Achilles tendon loading and walking speed while ambulating in an immobilizing boot. This paradigm provides a clinically implementable strategy to longitudinally monitor patient loading and activity while recovering from Achilles tendon injuries.