Urban Heat Island (UHI) effects adversely impact weather, air quality, and climate. Previous studies have attributed UHI effects to localized, surface processes. Based on an observational and modeling study of an extreme UHI (heat wave) episode in the Baltimore metropolitan region, we find that upstream urbanization exacerbates UHI effects and that meteorological consequences of extra-urban development can cascade well downwind. Under southwesterly wind, Baltimore, MD, experienced higher peak surface temperatures and higher pollution concentrations than did the larger urban area of Washington, DC. Ultra-high resolution numerical simulations with National Land Cover Data (NLCD) of 2001 show a nonlocal, dynamical contribution to UHI effects; when the upstream urban area is replaced by natural vegetation (in the model) the UHI effects could be reduced by more than 25%. These findings suggest that judicious land-use and urban planning, especially in rapidly developing countries, could help alleviate UHI consequences including heat stress and smog.