As Toronto's high-rise residential developments encroach on low-rise neighbourhoods, they alter the microclimate of the streets and parks below, posing significant challenges to parkettes' thermal comfort due to limited sunlight and wind conditions. This thesis investigates and assesses a small parkette's current winter thermal comfort levels in Yorkville, Toronto, and proposes temporary and permanent interventions to enhance its thermal comfort. This research aims to identify the most effective solutions given the existing conditions, using various methods such as policy and site planning scans, literature reviews, mapping, modelling, simulations, and COMFA analysis. Ultimately, this study yields a guide to evaluating and designing thermally comfortable temporary interventions in the urban spaces of Toronto.