The thermal environment is an important aspect of the urban environment because it affects the quality of life of urban residents and the energy use in buildings. Urban Heat Island (UHI) and Urban Cold Island (UCI) are complementary effects that are the consequence of cities’ structures interference with the local climate. This article presents results from five years of urban climate monitoring (2012–2016) in a small Portuguese city (Bragança) using a dense meteorological network of 23 locations covering a wide array of Local Climate Zones (LCZ), from urban areas to nearby rural areas. Results show the presence of both the UHI effect, from mid-afternoon until sunrise, and the UCI after sunrise, both being more intense under the dense midrise urban context and during the summer. Urban Green Spaces had an impact on both UHI and UCI, with an important role in cooling areas of the city during daytime in the summer. Other LCZs had less impact on local thermal conditions. Despite the small size of this city, both effects (UHI and UCI) had a relevant intensity with an impact on local climate conditions. Both effects tend to decrease in intensity with increasing wind speed and precipitation.