Fifth Street runs north-south in two fragments through central Woodland. Fifth Street north of Main Street roughly aligns longitudinally with Sixth Street south of Main Street. Fifth Street is set much closer to Fourth Street south of Main Street than north of Main Street.

The northern segment of Fifth Street runs from Beamer Street to Court Street. It intersects Grafton Street (which heads west only from 5th Street), Clover Street, Elliot Street (east only), North Street (5th Street jogs slightly to the southeast at North Street), and Hope Alley. Along the way, it passes by Sierra Mini Storage, El Buen Gusto Market, the Community Living Program, and the Animal Care Clinic of Woodland. Its south end faces Freeman Park across Court Street.

The northern segment of 5th Street has been planted with street trees by the city. The street trees include three invasive weed species: Glossy Privet (Ligustrum lucidum), Flowering Pear/Callery Pear (Pyrus calleryana), and Chinese Tallow Tree (Triadica sebifera). However, Modesto Ash/Arizona Ash is also planted here as a street tree and is native to California though not native to Woodland. Other non-native trees on the northern segment of 5th Street include Trident Maple (Acer buergerianum), Red Maple (Acer rubrum), Strawberry Tree (Arbutus unedo), Camphor Laurel (Camphora officinarum), European Hackberry (Celtis australis), Chinese Hackberry (Celtis sinensis), Maidenhair Tree (Ginkgo biloba), Kentucky Coffeetree (Gymnocladus dioicus), Goldenrain Tree (Koelreuteria paniculata), Crape Myrtle (Lagerstroemia indica), Chinaberry (Melia azedarach), Chinese Pistache (Pistacia chinensis), London Plane (Platanus × hispanica), Peach (Prunus persica), Idaho Locust (Robinia × ambigua 'Idahoensis'), and Chinese Elm (Ulmus parvifolia).

The southern segment of Fifth Street runs from Main Street to Gum Avenue. It intersects Lincoln Avenue, Oak Avenue, Cross Street, and Pendegast Street. Along the way, it passes by Nakamura Brothers Furniture, Enterprise Rent-a-Car, the Superior Court of California, County of Yolo Courthouse, Elfrink's Outdoor Power Equipment, the Woodland Police Department, Rancho Chain & Cable, and Nichols Plumbing. Its north end faces Freeman Park across Main Street.

The southern segment of 5th Street has also been planted with street trees by the city. The street trees here include four invasive weed species: Horsetail Tree/Beach Sheoak (Casuarina equisetifolia), Glossy Privet (Ligustrum lucidum), Purple-leaf Plum/Cherry Plum (Prunus cerasifera), and Flowering Pear/Callery Pear (Pyrus calleryana). However, they also include Interior Live Oak (Quercus wislizeni), which is native to Woodland, and Modesto Ash/Arizona Ash, which is native to other parts of California. Other non-native street trees on the southern segment of 5th Street include Norway Maple (Acer platanoides), Red Maple (Acer rubrum), Common Hackberry (Celtis occidentalis), Edible Fig (Ficus carica), Maidenhair Tree (Ginkgo biloba), Goldenrain Tree (Koelreuteria paniculata), Crape Myrtle (Lagerstroemia indica), Tulip Tree (Liriodendron tulipifera), Oleander (Nerium oleander), Chinese Pistache (Pistacia chinensis), London Plane (Platanus × hispanica), Northern Red Oak (Quercus rubra), Idaho Locust (Robinia × ambigua 'Idahoensis'), English Elm (Ulmus minor 'Atinia'), and Saw-leaf Zelkova (Zelkova serrata).