The City of Pagedale evolved from rural farmlands located on the outskirts of the City of St. Louis.  In the early 1800s, much of this area consisted primarily of large lots under single ownership.  These lots were used for apple, peach, and pear orchards, as well as a number of upland and riparian areas utilized for duck and game hunting, which is still exhibited in many of the streets’ names such as Mallard Drive and Ruddy Lane.

The primary landowners in the area were Andrew Roberston Jr. (who controlled almost all of the land between Page Avenue and Saint Charles Rock Road), George Kingsland, and the Watson Family.  And while many maps indicate that there was a major street aligning with what is Page Avenue today, there were few public roads in the area and most of these streets were not yet paved, which would make them impassable during spring thaws.  Sidewalks were typically constructed with heavy wood planks along the edge of the road, and large rock slabs were used at crossings. Thus, early infrastructure and pedestrian connectivity was limited to a few key streets through the area.

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