IS 44 passes through the lower half of Oakland. Sessions of the municipal Court are held on the second Monday of the month at 6:00 pm at Webster Groves Christian Church.

When the Missouri Pacific Railroad came to the area it drew many settlers and it was called "Hartwood". It was primarily the estate of Henry Clay Hart which was subsequently divided into subdivisions including Oakland Terrace and the Oaks; hence the name Oakland for the the railroad stop and then the community. In the 1940's, the Village of Oakland was incorporated as a fourth class city. There are three city parks in Oakland; Adolph Loewnau, Monaco and Oakland Backstoppers. Backstoppers Park is part of Grant's Trail and has a playground, picnic tables and a gazebo with areas for biking, walking and free play. Loewnau Park is a present a large open are where the annual Community picnic is held. Monaco Park is a pocket park with a small soccer field, swing set, slides, climbers and a gazebo.

Hon. Paul Hunker