Trees in urban environments hold significant value in providing ecosystem services, which will become increasingly important as urban populations grow. Tree phenology is highly sensitive to climatic variation, and resultant phenological shifts have significant impact on ecosystem function. Data on urban tree phenology is important to collect. Typical remote methods to monitor tree phenological transitions, such as satellite remote sensing and fixed digital camera networks, are limited by financial costs and coarse resolutions, both spatially and temporally and thus there exists a data gap in urban settings. Here, we report on a pilot study to evaluate the potential to estimate phenological metrics from imagery acquired with a conventional dashcam fitted to a car. Dashcam images were acquired daily in spring 2020, March to May, for a 2000 m stretch of road in Melksham, UK. This pilot study indicates that time series imagery of urban trees, from which meaningful phenological data can be extracted, is obtainable from a car-mounted dashcam. The method based on the YOLOv3 deep learning algorithm demonstrated suitability for automating stages of processing towards deriving a greenness metric from which the date of tree green-up was calculated. These dates of green-up are similar to those obtained by visual analyses, with a maximum of a 4-day difference; and differences in green-up between trees (species-dependent) were evident. Further work is required to fully automate such an approach for other remote sensing capture methods, and to scale-up through authoritative and citizen science agencies.