Quantifying aspects related to riding helps cyclists keep track of their performance. Being able to track performance enables a greater understanding of athleticism, strength and endurance required to work on areas of potential improvement. The technology solutions currently available on-the-field facilitate real-time monitoring of these determinants. These solutions render accurate measurements of primary parameters such as cycling speed, cadence and pedal force. However, there is a lack of compact and integrated solutions to quantify the effect of external factors like terrain and slope. Integration of these features along with the measurement of primary parameters enables a comprehensive understanding of ride behaviour and handling. This paper presents a system to quantify these diverse aspects for a single speed bicycle using a single inertial sensor device. Computations on measurements are done on the device and results are transmitted wirelessly to a smartphone. The device is attached to the rear wheel, and it measures primary parameters such as cycling speed and cadence. Relative pedal force, acceleration and braking metrics are derived from the variations caused in the speed profile computed. Terrain and slope affect these derived parameters, and therefore the changes caused by them are measured to obtain relativistic information on the effect of these external factors. Real-time visualization of primary aspects and long term monitoring of performance under the influence of varying external factors benefit cyclists with insights for training and improvement. © 2019 IEEE.