Urban areas alter local atmospheric conditions by modifying surface albedo and consequently the surface radiation and energy balances, releasing waste heat from anthropogenic uses, and increasing atmospheric aerosols, all of which combine to increase temperatures in cities, especially overnight, compared with surrounding rural areas, resulting in a phenomenon called the `urban heat island` effect. Recent rapid urbanization of the planet has generated calls for remote sensing research related to the impacts of urban areas and urbanization on the natural environment. Spatially extensive, high spatial resolution data products are needed to capture phenological patterns in regions with heterogeneous land cover and external drivers such as cities, which are comprised of a mixture of land cover/land uses and experience microclimatic influences. Here we use the 30 m normalized difference vegetation index (NDVI) product from the Web-Enabled Landsat Data (WELD) project to analyze the impacts of urban areas and their surface heat islands on the seasonal development of the vegetated land surface along an urban-rural gradient for 19 cities located in the Upper Midwest of the United States. We fit NDVI observations from 2003-2012 as a quadratic function of thermal time as accumulated growing degree-days (AGDD) calculated from the Moderate-resolution Imaging Spectroradiometer (MODIS) 1 km land surface temperature product to model decadal land surface phenology metrics at 30 m spatial resolution. In general, duration of growing season (measured in AGDD) in green core areas is equivalent to duration of growing season in urban extent areas, but significantly longer than duration of growing season in areas outside of the urban extent. We found an exponential relationship in the difference of duration of growing season between urban and surrounding rural areas as a function of distance from urban core areas for perennial vegetation, with an average magnitude of 669 AGDD (base 0 °C) and the influence of urban areas extending greater than 11 km from urban core areas. At the regional scale, relative change in duration of growing season does not appear to be significantly related to total area of urban extent, population, or latitude. The distance and magnitude that urban areas exert influence on vegetation in and near cities is relatively uniform.