Twin Oaks, one of St. Louis County’s best kept secrets, is a small fast-growing city of approximately 610 residents. Its 0.27 square miles of streets are nestled between Manchester to its northeast, Valley Park to its south and unincorporated St. Louis County to its west, radiating from the intersection of Big Bend Road and Highway 141.
The name "Twin Oaks" originated from two oak trees located near the intersection of Crescent Road and Crescent Avenue at the southwest end of the city.
In 1925, James Stoker owned a vegetable farm with a great deal of acreage. Stoker and others at the time, who also owned a lot of acreage, did not want any further increases in taxes. Valley Park, however, was interested in annexing the area which would result in increased taxes. In order to avoid this, James Stoker and his neighbors created the "Village of Twin Oaks" in 1938. In order to pay for street improvements, the residents would hold fish fries to collect money and then do the work themselves.
The first neighborhood within the Community, which local residents now respecfully call "Old Town," started in the late 1950’s and consisted of approximately 30 homes developed on Quinette Drive, First Street, Ann Avenue and Meramec Station Road. By the end of the 1960’s, 15 more homes were built on Boly Lane and Crescent Avenue. With the completion of Interstate 44 in 1972, a new phase of development was seen. The Birnamwood Condominium Complex was built in 1976 consisting of 78 units along Birnamwood Trail Drive and Autumn Leaf Drive. The builder, Cinco Development Company, received an architectural award for the unique construction which blended the buildings into the natural environment. By the end of 1983, approximately 43 single-family homes were built on Golden Oak Court and Autumn Leaf Drive. Then from 1983 to 2000, additional homes were added on Woodland Oaks Drive and Boly Lane.
In 1984, the Village Board contracted for a comprehensive Long Range Master Plan which would guide future development and ensure financial viability. Twin Oaks received an award from the American Planning Association for this master plan. The Village commenced the annexation of properties at the northeast and northwest corners of the intersection of Big Bend and old Highway 141. Those properties were commercially developed with the resulting revenues affording the (now) City the ability to offer its residents services matching those of many larger cities.
The first retail development was Big Bend Square, which opened in 1978. The Commerce Bank corner was originally developed as a marketing test site featuring a drive-thru only McDonalds. Commercial businesses are plentiful for such a small community featuring a supermarket, drug store, sit-down and fast-food restaurants and a variety of businesses such as banking, dental care, eye care, construction, hair/nail care, dry cleaning, tax preparation and legal services.
In the late 1980’s, the State Highway Department purchased 10 homes for the widening and relocation of Highway 141, reducing the population and splitting the Village in half.
In the early 1990’s, Twin Oaks acquired 9 acres off Ann Avenue adjacent to Twin Oaks Presbyterian Church to create a “pedestrian park.” In 1994, the Park opened with amenities including a pavilion, gazebo, playground, restrooms, tennis, basketball and volleyball courts, lake and walking path. Twin Oaks Park has gained the reputation of one of the most beautiful parks in St. Louis County and draws visitors from all over the metropolitan region. Twin Oaks sponsors a variety of annual events including concerts, family fun day, Easter egg hunt, and a spectacular July 3rd fireworks display.
Later in the 1990's, Twin Oaks Presbyterian Church was constructed just west of Big Bend Square.
In 2016, Twin Oaks residents voted to change the status of the community from a Village to a Fourth-Class City giving the municipality more power in an ever-changing political atmosphere. Between 2014 and ending in 2017 the City prevailed in a first amendment challenge by a commercial photographer over park permitting regulations. The Court determined that the City's regulation of commercial activities in the City's park, including those involving First Amendment rights, were a reasonable exercise of the City's police powers and were narrowly tailored to address the problems that the City was experiencing. The success of this lawsuit has potential implications for parks nation-wide.
In 2018/2019, the Big Bend Square Redevelopment project, a mixed use/planned development project, was completed. This included a facelift for all the existing businesses within the shopping area as well as new buildings, with additional retail establishments on the bottom level of one of the buildings and the remaining consisting of "The Villages of Twin Oaks," featuring 219 new apartments with all the amenities. As a result, the population of Twin Oaks will possibly double once fully occupied. At nearly the same time, the City began construction on its new Town Hall, which in addition to expanded office/staff space, has a beautiful new Board room for public meetings and a Community Room which is also available for use for both City and community purposes.