Head-worn inertial sensors represent a valuable option to characterize gait in real-world conditions, thanks to the integration with glasses and hearing aids. Few methods based on head-worn sensors allow for stride-by-stride gait speed estimation, but none has been developed with data collected in real-world settings. This study aimed at validating a two-steps machine learning method to estimate initial contacts and stride-by-stride speed in real-world gait using a single inertial sensor attached to the temporal region. A convolutional network is used to detect strides. Then, stride-by-stride gait speed is inferred from the detected cycles by a gaussian process regression model. A multi-sensor wearable system was used to label over 100,000 strides recorded from 15 healthy young adults during supervised acquisitions and real-world unsupervised walking. The stride detector achieved high detection rate (F1-score > 92%) and accuracy (mean absolute error < 40 ms). Very strong correlation between target and predicted speed (Spearman coefficient > 0.86) and low mean absolute error (< 0.085 m/s) were observed. The method proved valid for the quantitative evaluation of stride-by-stride gait speed in real-world conditions. These findings lay the technical and analytical groundwork for future clinical validation and application of gait analysis frameworks that integrate inertial sensors with head-worn devices.