Internet of Things (IoT)-based solutions for sport analytics aim to improve performance, coaching, and strategic insights. These factors are especially relevant in cycling, where real-time data should be available anytime, anywhere, even in remote areas where there are no infrastructure-based communication technologies (e.g., LTE and Wi-Fi). In this article, we present an experience report on the use of state-of-the-art IoT technologies in cycling, where a group of cyclists can form a reliable and energy efficient mesh network to collect and process sensor data in real-time, such as heart rate, speed, and location. This data is analyzed in real-time to estimate the performance of each rider and derive instantaneous feedback. Our solution is the first to combine a local body area network to gather the sensor data from the cyclist and a 6TiSCH network to form a multihop long-range wireless sensor network in order to provide each bicycle with connectivity to the sink (e.g., a moving car following the cyclists). In this article, we present a detailed technical description of this solution, describing its requirements, options, and technical challenges. In order to assess such a deployment, we present a large publicly available data-set from different real-world cycling scenarios (mountain road cycle racing and cyclo-cross) which characterizes the performance of the approach, demonstrating its feasibility and evidencing its relevance and promising possibilities in a cycling context for providing low-power communication with reliable performance.