Urban heat island conditions increase heat exposure and constrain safe outdoor activities. Urban forests can mitigate thermal loads; however, stand morphology can produce divergent microclimates. We aimed to quantify how stand type (open vs. closed), season (spring, summer, fall), and activity intensity (MET 1.0–6.0) jointly modulate thermal comfort and to identify season-specific optimal MET levels in an urban forest in Daejeon, Republic of Korea. We combined site-specific 3D canopy modeling with hourly Predicted Mean Vote (PMV) simulations driven by AMOS tower data (2023–2024). Comfort was defined as |PMV| ≤ 0.5. Analyses included seasonal means, Cliff’s delta, and generalized estimating equation logistic models to estimate the SITE × SEASON × MET interactions and predict comfort probabilities. Across most seasons and MET levels, C1 was more comfortable than C2. However, at MET 1.0 in summer, the pattern was reversed, which may reflect the canopy shading and associated decreases in mean radiant temperature (MRT) of C2. Comfort peaked at MET 2.0–3.0 and declined sharply at ≥4.5 MET. The three-way SITE × SEASON × MET interaction was significant (p < 0.001). The season-specific optimal MET values under our boundary conditions were 3.0 (spring), 2.0–2.5 (summer), and 3.0 (fall). These simulation-based PMV-centered findings represent model-informed tendencies. Nevertheless, they support actionable guidance: prioritize high-closure stands for low-intensity summer use, leverage open stands for low-to-moderate activities in spring and fall, and avoid high-intensity programs during warm periods. These results inform the programming and design of urban-forest healing and recreation by matching stand type and activity intensity to season to maximize comfortable hours.