Cover crops can lessen soil erosion and compaction, improve water infiltration, enhance nutrient availability, suppress weeds, and assist with pest management. However, cover crops are not commonly used in alleyways of established red raspberry (Rubus idaeus) fields in the Pacific Northwest of the United States. Rather, the space between red raspberry beds is repeatedly cultivated and the soil is kept bare, which has detrimental effects on soil quality. Adoption of alleyway cover crops is limited because red raspberry growers are concerned about resource competition between a cover crop and red raspberry crop. A 2-year study was conducted in an established ‘Meeker’ red raspberry field in northwest Washington to evaluate the effects of eight annually seeded alleyway cover crops (cultivars of wheat, cereal rye, triticale, oat, and ryegrass), one perennial ryegrass alleyway cover crop, mowed weed vegetation, and the industry standard of cultivated bare soil (Till) on the physical, chemical, and biological properties of soil quality in alleyways and raised beds. This included evaluating soil bulk density (Db), compaction, organic matter, pH, cation exchange capacity (CEC), macro- and micronutrients, and bacterial and fungal community structure; red raspberry yield and fruit quality were also evaluated. Although there were statistically significant differences among treatments across sampling dates for CEC, there were no consistent trends. Alleyways planted with the perennial ryegrass mix had the lowest mean Db 6 and 24 months after seeding. Tilled alleyways had the lowest Db 12 and 18 months into the study. Red raspberry grown adjacent to Till did not result in a significantly higher estimated yield or fruit total soluble solids than raspberry grown adjacent to cover crops in either year of the experiment. Differences in microbial community structure were observed among seasons rather than treatments. These results do not demonstrate significant effects of alleyway cover crops on red raspberry productivity when applied to established fields. The potential benefits of alleyway cover cropping on soil quality may outweigh any concerns regarding resource competition. Changes in soil quality are often difficult to quantify and require long-term study.