The origin of Pepper Pike’s name remains uncertain, with some maintaining that it was named after an early settler and others insisting it derived from the pepper trees once found here. In either event, today’s city has its origins in historic Orange Township, of which it was once part. The area was settled beginning in about 1820, when it was traversed by stagecoach lines running between Cleveland and both Chagrin Falls and Pittsburgh. In 1824, the Ohio legislature chartered State Route 422, which later became Chagrin Boulevard, and spurred the first round of modest development.
Still, until well into the 20th century, it was primarily a farming community, with cheese-making a primary industry. Although still rural at the turn of the 20th century, the city’s growth was stimulated by the building of the Chagrin Falls-Cleveland interurban railway in 1897, which made the community easily accessible to downtown Cleveland with its hourly service, until the trains were discontinued in 1924, a victim of the automobile (although a Rapid Transit line along the same right of way later stretched almost to Pepper Pike). The city’s location would be considerably enhanced with the arrival of nearby Interstate-271 in the 1960s.
In many respects, the city’s real founders were the famous Van Sweringen brothers, Oris Paxton and Mantis James, who developed Shaker Heights and built Cleveland’s Terminal Tower, before later going bankrupt during the Great Depression. Historians have written that developing the areas east of Shaker Heights, including the area now called Pepper Pike, all the way to the Chagrin Valley were the brothers’ “third dream,” after building Shaker and their railroad empire. They began buying farmland in the area as early in 1910, and by the 1920s were acquiring larger parcels and drafting development plans, which included paving roads. Land prices began rising, along with the population, and by 1924 Orange Township was split into five villages, including Pepper Pike, which had been until then been known as Orange Hill.
While financial setbacks in the 1930s prevented the brothers from finishing the job (they died within a year of each other in 1935 and 1936), they nevertheless laid much of the groundwork for the area’s later success.