The western portion of the Pacific Northwest is known for being dry in the summer and cool and humid in the other months. Tall fescue is valued for its drought and heat tolerance, making it a desirable choice in regions where water is scarce and often restricted by legislation during periods of drought in the summer. However, cool and humid climates make it challenging to manage tall fescue in the winter because unacceptable quality is often observed due to low-temperature diseases and thinning in turf. A field trial was initiated in Autumn 2020 in Corvallis, OR, USA to assess the effects of mowing height as well as fertility timing and rate on tall fescue performance. Two mowing heights of 5.1 and 7.6 cm, four seasonal fertility timings, and three levels of annual N rates of 98, 196, and 294 kg·ha−1·yr−1 were evaluated using a 2 × 4 × 3 factorial experiment in a strip-plot design. Quantitative data of percent green cover and normalized difference vegetation index (NDVI) suggest that autumn fertilization is needed in cool, humid areas where tall fescue is actively growing in the winter months. The annual fertilization rate of 294 kg·ha−1·yr−1 N produced higher green turf cover and NDVI, compared with 98 or 196 kg·ha−1·yr−1 N. Furthermore, divergent effects of mowing heights were observed during winter compared with other months, suggesting that tall fescue could be mowed lower at 5.1 cm during cool, humid winter months and higher at 7.6 cm in other seasons for better overall turfgrass growth and less winter disease and thinning. Our research provides practical cultural practices for managing tall fescue turf in the Pacific Northwest or similar climates.