This paper comprehensively evaluates Long-Range Frequency Hopping Spread Spectrum (LR-FHSS) modulation for urban and aerial IoT scenarios, comparing it with the established Long Range (LoRa) modulation in LoRaWAN networks. LR-FHSS offers a promising alternative to LoRa by efficiently utilizing the available spectrum, enhancing device capacity, and minimizing collisions in dense deployments. Using a range of performance metrics, including Packet Delivery Ratio (PDR) and Received Signal Strength Indicator (RSSI), we experimentally assess LR-FHSS's performance across varied data rates, payload lengths, and coding rates. Our urban and elevated balloon based measurements provide the first real-world insights into LR-FHSS's potential for dense urban networks and sparse aerial applications. Our results reveal conditions where LR-FHSS outperforms LoRa, offering deployment guidelines for Internet of Things (IoT) networks that require high reliability and scalability. We make the resulting dataset publicly available to the community, marking the first dataset for advancing LR-FHSS research and applications.