John Henry Patterson, industrialist and founder of the National Cash Register Corporation, is considered the "Father of Oakwood.

At the turn of the twentieth century, Oakwood was primarily farmland situated on a hill directly south of the City of Dayton.

"[6] In light of this real estate advantage and its location adjacent to the City of Dayton, Oakwood's largest period of growth began and by 1930, the population numbered over 6,000.

One of the city's early residents was Orville Wright, whose home, Hawthorn Hill, still stands at the corner of Harman and Park Avenues.

John H. Patterson, founder of the National Cash Register Company (NCR) also called Oakwood home.

During World War II, the Runnymede Playhouse in Oakwood hosted Unit IV of the Dayton Project.

According to the United States Census Bureau, the city has a total area of 2.193 square miles (5.68 km2), all land.

Because of the city's age, many of the houses were constructed before World War II and are older in design.

The western end of the city features many large properties and historic houses, such as Hawthorn Hill, home of Orville Wright.

The city itself gives "Beautification Awards" to the judged most beautiful houses in order to maintain this high level of aesthetic awareness.

Wright Memorial Library[8] offers similar aesthetics, and the police and fire department is reminiscent of a French château.

One contiguous junior and senior high school provides education for all Oakwood students grades seven through twelve.

Oakwood High School graduated its first senior class in 1924 and began the practice of the Baccalaureate ceremony at Westminster Presbyterian Church in downtown Dayton.

The end of an Oakwood student's experience is the Senior Awards, Baccalaureate, and Commencement ceremonies.

Oakwood High School's English, mathematics, natural science, and foreign language courses are matched by many performing arts opportunities for its students.

It is not uncommon for Oakwood's top academic graduates to gain acceptance to some of the most selective universities and colleges in the United States and the world.

In 2023, Greater Dayton Regional Transit Authority (GDRTA) deemed their trolley system obsolete, citing maintenance costs and investment in alternative technology.

The trolley lines along Far Hills Avenue through Oakwood and Kettering had not been in use since 2016 despite being along major GDRTA routes service the southern suburbs of Dayton.