The early 1900s saw Oak Park as a culturally-thriving and economically-vibrant destination neighborhood,[2][3] due in part to its strong sense of community and its ties with and proximity to the historic site of the California State Fairgrounds.

However, Oak Park was never able to fully recover due to the effects of the Great Depression compounded by discriminatory practices.

Before World War II, like many cities, Oak Park experienced redlining which segregated neighborhoods by race.

[5] The 1960s interstate freeway expansion program physically divided many historic Sacramento neighborhoods like Oak Park, creating isolated areas of poverty or relative prosperity.

During the 1980s and 1990s, further deterioration of the living standards were exacerbated by frequent occurrences of petty theft, street crime, drug activities, and gang-related violence.

The street was home to the Piggly Wiggly, Park Meat Market, and Arata Bros markets; Steen's Corner Saloon; Azevedo's Women's Apparel; Janek and Scurfield canvass goods; Citizens Bank of Oak Park; the Ben Franklin variety store; and many others.

Meanwhile, a short Route 5 would run east from the Oak Park terminus and end at the Historic site of the California State Fair grounds on Stockton Boulevard.

[10] As of 2008, Oak Park faced a variety of challenges sustaining the beginnings of its comeback, due in part to an increase in foreclosures and an area-wide decline in property values.

A few notable restaurants are Vibe Health Bar, KC Kombucha, Fixins, Faria, and Oak Park Brewing Co.[11]