Cleveland Street and North Cleveland Street are north-south streets that are longitudinally aligned with one another but do not connect to one another.

North Cleveland Street

North Cleveland Street runs between Kentucky Avenue and Beamer Street in northern Woodland. It is situated east of North West Street and west of North Walnut Street. From north to south, it intersects William Avenue/Emerald Street, Stoll Avenue (which heads west only from North Cleveland Street), Woodland Avenue, Frost Drive (west only), and Plane Avenue (east only). Its south end faces Christiansen Park.

Cleveland Street

Cleveland Street runs between Elliot Street and Casa Linda Drive in central Woodland. It is situated east of Grand Avenue and McKinley Avenue and west of Walnut Street and Elm Street. From north to south, it intersects Plaza Alley (which heads west only from Cleveland Street), North Street (which jogs slightly southeast at Cleveland Street), Fire Alley (west only), Court Street, Dead Cat Alley (east only), Main Street, Lincoln Avenue, Oak Avenue, Park Avenue (west only), West City Park Alley (west only), Cross Street, Clanton Way (east only), Clanton Avenue (west only), Pendegast Street, Bartlett Avenue, Marshall Avenue, Hays Street, Hermosa Place (northeast only), and Maedell Way. Along the way, it runs past Nugget Markets and City Park.

Cleveland Street has been planted with street trees by the city. The street trees include the invasive weed species Purple-leaf Plum/Cherry Plum (Prunus cerasifera) but also Valley Oak (Quercus lobata), which is native to Woodland, and Modesto Ash/Arizona Ash (Fraxinus velutina), which is native to other parts of California. Other non-native street trees on Cleveland Street include Chinese Hackberry (Celtis sinensis), Chinese Fringe Tree (Chionanthus retusus), Crape Myrtle (Lagerstroemia indica), and London Plane (Platanus × hispanica).