Tucked into just 0.27 square miles of St. Louis County, Twin Oaks is a small but vibrant community often described as one of the region’s best-kept secrets. Home to approximately 600 residents, the city is strategically situated at the crossroads of Big Bend Road and Highway 141, bordered by Manchester to the northeast, Valley Park to the south, and unincorporated St. Louis County to the west.

The city’s name comes from two stately oak trees that once stood near the intersection of Crescent Road and Crescent Avenue at the southwest edge of town—simple landmarks that became lasting symbols of the community.

Twin Oaks’ story began in the early 20th century when the area was largely farmland. In 1925, James Stoker owned a sizable vegetable farm, along with several neighbors who shared a common concern: rising taxes. When nearby Valley Park sought to annex the area, Stoker and fellow landowners took action. In 1938, they incorporated the Village of Twin Oaks, preserving local control and independence. In true grassroots fashion, early residents funded street improvements by hosting fish fries and completing much of the work themselves.

Residential development began to take shape in the late 1950s with the creation of what is now affectionately known as “Old Town.” Approximately 30 homes were built along Quinette Drive, First Street, Ann Avenue, and Meramec Station Road. Growth continued through the 1960s with additional homes on Boly Lane and Crescent Avenue. The completion of Interstate 44 in 1972 marked a new era of expansion, including the construction of the award-winning Birnamwood Condominium Complex in 1976. Designed to blend seamlessly into the natural landscape, the 78-unit development received architectural recognition for its thoughtful design.

By the early 1980s, single-family homes expanded onto Golden Oak Court, Autumn Leaf Drive, Woodland Oaks Drive, and Boly Lane. In 1984, the Village Board commissioned a comprehensive Long-Range Master Plan to guide responsible growth and ensure financial stability. The plan earned an award from the American Planning Association and helped shape strategic annexations at Big Bend Road and Highway 141. Commercial development in these areas provided revenue that allowed Twin Oaks to offer services comparable to those of much larger cities.

Retail development also played a key role in the city’s evolution. Big Bend Square opened in 1978, becoming the community’s primary commercial hub. One corner of the development even served as a marketing test site for a drive-thru-only McDonald’s. Today, Twin Oaks supports an impressive variety of businesses for a city of its size, including grocery, pharmacy, dining, banking, healthcare, personal services, and professional offices.

The late 1980s brought significant change when the State Highway Department purchased ten homes to widen and realign Highway 141, temporarily reducing the population and physically dividing the community. Despite this challenge, Twin Oaks continued to invest in quality-of-life improvements.

In the early 1990s, the city acquired nine acres off Ann Avenue to create Twin Oaks Park. When it opened in 1994, the park featured a pavilion, gazebo, playground, restrooms, courts for tennis, basketball, and volleyball, a lake, and a walking path. Today, Twin Oaks Park is widely regarded as one of the most beautiful parks in St. Louis County and hosts popular annual events, including concerts, Family Fun Day, an Easter egg hunt, and a signature July 3rd fireworks celebration.

Twin Oaks continued to evolve in the decades that followed. The Presbyterian Church was constructed in the late 1990s, further anchoring the community. In 2016, residents voted to transition from a village to a Fourth-Class City, providing greater municipal authority. Around the same time, the city successfully defended its park permitting regulations in a First Amendment challenge—an outcome with implications for park management nationwide.

A major milestone came in 2018–2019 with the redevelopment of Big Bend Square. The mixed-use project revitalized existing businesses, added new retail space, and introduced The Villages of Twin Oaks, a 219-unit apartment community. Once fully occupied, the development effectively doubled the city’s population. Concurrently, Twin Oaks constructed a new Town Hall featuring expanded offices, a modern boardroom, and a Community Room available for public use.

Today, Twin Oaks remains a highly desirable place to live and work within the St. Louis metropolitan area. Recent additions such as ALDI, Ace Hardware, SavOn Liquor and Wine, Dunkin’, Carreta’s Mexican Restaurant, Bartolino’s, Sauce on the Side, and Rosemary Coffee Co. reflect the city’s continued growth while preserving the close-knit character that has defined Twin Oaks for nearly a century.