The Oakland Area comprises the district to the south or Forest Park from Kingshighway west to the city limits with Interstate Highway 44 as its southern boundary.
Its principal topographic feature is the valley of the River des Peres, which emerges from the park a short distance west of Kingshighway and then crosses the eastern part of the Oakland area to a point south of Manchester Avenue. At that point it assumes a southwesterly direction, generally parallel to the Frisco Railway and finally crosses the railroad and Highway 44 near the western city limits. Land on both sides of the valley naturally slopes toward the old river bed, and north of Manchester Avenue the ground rises both to the north and west, culminating in some of the city's highest elevations, near Oakland and McCausland Avenues. This vicinity is appropriately named Hi-Pointe.
Originally this area was a part of the Gratiot League Square, so called because it was intended to be three miles square, although it was later slightly shortened on its western side. Its northern limit was a line bisecting Forest Park, on the south it reached to the present Bancroft Avenue and in an east-west direction it extended from Kingshighway to Big Bend Road. Charles Gratiot was a French immigrant who settled in Cahokia in 1777 and moved to St. Louis in 1781. In that year he married Victoire Chouteau, a sister of Auguste Chouteau, one of the founders of St. Louis. He applied to the Spanish Lieutenant-Governer Cruzat in 1785 for a large land grant to the west of the Prairie des Noyers Common field. After a survey by Antoine Soulard in 1796, its area was found to be 5,716 acres.
Gratiot's claim to it was approved by the territorial government at New Orleans in 1798, after which he built a log house on the property and cultivated a farm. After the transfer of the Louisiana Territory to the United States, Gratiot's grant was confirmed by the Board of Land Commissioners in 1808 as U. S. Survey 2037. In later years, Gratiot became a judge and was chairman of the board of trustees for the town of St. Louis, as well as organizer of the Bank of Missouri.