‘Montmorency’ tart cherry trees (Prunus cerasus L.) are grown commercially in the United States in low-density systems. Commercial tart cherry orchard design has not changed significantly over the past 50 years, but there is some variation from farm to farm in management strategies, including tree spacing, training, and pruning, and the resulting orchard production and turnover. Canopy dimensions and dynamics are important considerations for evaluating and improving orchard management strategies but are not well documented for tart cherry systems. Current orchard design and canopy management strategies were surveyed along a gradient of orchard age across five commercial farming operations in Utah. Trunk cross-sectional area and various canopy dimensions, including spread and volume, were quantified to capture tree size and canopy architecture. The survey indicated a surprising lack of deviation in orchard design in the region over the last several decades with higher variation among blocks within a farm than across farms. As a result, the survey revealed trends in tree growth and canopy structure across the range in orchard ages despite differences in management approaches of the surveyed farms. These trends were useful in illustrating canopy development and space fill. Tree age between 11 and 15 years after planting was determined to represent a transition between establishment and mature growth, where canopies filled available row space and began experiencing senescing canopy structure. Based on the distribution of ages captured in the survey, a significant number of orchards in Utah are at an age range of 11–15 years, perhaps contributing to superior yields per land area reported for the region. The confluence of space-fill and canopy development described in this study highlights a critical period for tart cherry orchard management at the transition of canopy establishment and maturity. These baseline dynamics will provide benchmarks for evaluating strategies for refining and improving orchard management systems for tart cherry in the Intermountain West region.