Developing quantified establishment period estimates for newly planted trees will help set realistic goals for plant performance in the urban landscape. Nine years of tree planting records obtained from the city of Boston, MA and the town of Brookline, MA were used to derive samples of trunk caliper for hedge maple (Acer campestre), London planetree (Platanus x acerifolia), and red oak (Quercus rubra). Several site characteristics were measured to identify effects on newly planted tree growth. Breakpoint estimates of the piecewise regression models fell at 4 years and 6 years for London planetree and hedge maple respectively, showing establishment periods for urban trees are longer than the conventional 3 years. Pit area has a significant effect on caliper growth for London planetree and red oak, with larger growing spaces yielding larger trees. Observed soil bulk densities did not have a significant effect on caliper measurement for any of the species tested. Mean soil bulk density was 1.4 g/cm3, 1.45 g/cm3, and 1.49 g/cm3 for hedge maple, London planetree, and red oak respectively. Soil texture was significant for hedge maple only, with percent clay showing significant positive effects and percent sand as marginally significant. Pit type showed a significant effect on caliper measurement of London planetree with grass strips producing the largest caliper trees followed by open pits. Planting locations with tree grates produced the smallest caliper trees. Presence of perforated air vents produced significantly larger caliper trees than sites with an air vent present for red oak.