In the first half of the nineteenth century, the present Shaw area was bounded by roadways marking the eastern and western limits of the Prairie des Noyers. These later became Grand and Kingshighway Boulevards. East-west access was by means of the Old Manchester and Arsenal Street Roads. The latter followed a course westward from the St. Louis Arsenal to a junction with Manchester Road at what is now Maplewood. Old Manchester, whose route is now traversed by South Vandeventer and Southwest Avenues, was designated as a state road in 1839 and became known as the Road to Jefferson City. The present Manchester Avenue was then called the Fox Creek Road, and received its new name after completion of the adjacent Pacific Railroad. Both Manchester Roads were extensions of Market Street in St. Louis.

Grand Boulevard was originally platted and named by Hiram W. Leffingwell in 1850. He envisioned a broad parklike thoroughfare extending from Carondelet to Bremen, along a high ridge line. Such an idea was too advanced for the County Court, which limited the street to its existing width of eighty feet. Kingshighway is so-called from the custom of naming the public roads giving access to the ends of the common fields, as the Rue Royale or King's Road. It remained relatively unimportant until 1903 when the City's Kingshighway Boulevard Commission planned it as part of the fifteen mile Kingshighway Parkway system.

A good index of a neighborhood's history can be found in the names of its streets. In the Shaw Tower Grove area, the dominant influence of Henry Shaw is evident in the horticultural derivation of such names as Botanical, Flora, Magnolia, Hortus, and, of course, in Shaw and Tower Grove Avenues. Political connotations are apparent in streets named for Grover Cleveland, his wife Frances Folsom and his opponent James G. Blaine. These names were bestowed by subdivision developers who were trying to attract attention from visitors to the 1888 Democratic national convention here.

Engineers are commemorated by streets named for Henry W. Flad, assistant to Eads on the bridge construction, and for Richard Klemm, who laid out many early subdivisions.

Land owners are represented by Mrs. Mary McRee and the Gurney and Heger families, as well as by Shawl Lawrence Avenue honors Mary Lawrence Tyler, former owner of the Tyler Place tract. Henry S. Geyer and Samuel Reber were St. Louis lawyers, while Russell Boulevard memorializes the owners of the Oak Hill area clay mines. Personages of an earlier day honored by street names are Henri de Tonty, lieutenant of explorer Robert LaSalle, and the Marquis de Lafayette. Waterways are recalled by Shenandoah Avenue, named after the river in Virginia, and Spring Avenue, a southerly extension of a North St. Louis street named for the source of the Rocky Branch Creek. In the 1860's, Shaw named that part of present Spring Avenue from McRee to Shaw, as Morisse Street in honor of his brother-in-law. During the 1880's, this same street section was called Mercy Street. That part of 39th Street north of Park Avenue was once named Tiffany Street and 39th was once called Vandeventer.