In the UK, tree, hedgerow, and woodland (THaW) habitats are key havens for biodiversity and support many related ecosystem services. The UK is entering a period of agricultural policy realignment with respect to natural capital and climate change, meaning that now is a critical time to evaluate the distribution, resilience, and dynamics of THaW habitats. The fine-grained nature of habitats like hedgerows necessitates mapping of these features at relatively fine spatial resolution—and freely available public archives of airborne laser scanning (LiDAR) data at <2 m spatial resolution offer a means of doing so within UK settings. The high cost of LiDAR prohibits use for regular monitoring of THaW change, but space-borne sensors such as Sentinel-1 Synthetic Aperture Radar (SAR at ca. 10 m resolution) can potentially meet this need once baseline distributions are established. We address two aims in this manuscript—(1) to rapidly quantify THaW across UK landscapes using LiDAR data and (2) to monitor canopy change intra- and inter-annually using SAR data. We show that workflows applied to airborne LiDAR data can deliver THaW baselines at 2 m resolution, with positional accuracy of >90%. It was also possible to combine LiDAR mapping data and Sentinel-1 SAR data to rapidly track canopy change through time (i.e., every 3 months) using, cloud-based processing via Google Earth Engine. The resultant toolkit is also provided as an open-access web app. The results highlight that whilst nearly 90% of the tallest trees (above 15 m) are captured within the National Forest Inventory (NFI) database only 50% of THaW with a canopy height range of 3–15 m are recorded. Current estimates of tree distribution neglect these finer-grained features (i.e., smaller or less contiguous THaW canopies), which we argue will account for a significant proportion of landscape THaW cover.