Early Yucaipa Valley - South Bench
The Yucaipa Valley was naturally divided into three benches, or mesa-like areas, each divided from the other by washes emanating from the foothills. The North and Central benches later 
became known as Yucaipa and the South Bench later became known as Calimesa. The Indians of the area were the Serranos and the Cahuillas. The Serranos settlement was near the Sepulveda Adobe in Yucaipa and the Cahuillas settlement was in Cherry Valley. The Stagecoach Trail went from Redlands, following San Timoteo and Woodhouse Road to Singleton Canyon and dropping into Cherry Valley. The stage stop in Calimesa was located at the end of Singleton Road and referred to by the horseback riders as Stagecoach Road. In 1910 the trail was cut off and the area stockmen had it designated as a dedicated stock trail to protect their right of passage to drive their stock.
Prior to the arrival of the early pioneers, the entire area had been cattle grazing land. Several thousand acres of land were given to a state surveyor as partial payment for his services when the state treasury was low on funds. He received land parcels in vast amounts from the border to Sacramento as his paycheck for his surveying services to the State. He apparently made no attempt to develop the land. Following his death, the land was released to homesteaders.
How Calimesa got its name and the establishment of the Calimesa Post Office
It was in 1929 that Calimesa was given its name and its first post office established. When there were between 40 and 50 families living in the South Bench area they felt the need for their own post office. In order to convince the government that they needed one, they had to first have a name unlike any other name in the post office files of the Government. The Calimesa Community Club was officially established in 1929 as a direct result of the residents’ desire for a post office. Earl Davenport, Marion Bise and Ernie Lord were members of the Community Club and each served as President at one time or another.
About 125 people attended a public
meeting to decide on a name. Harry Sheppard, who later became a congressman, was chairman of the meeting. It was held in the Hi-Way Trucking Company garage located on what is now Calimesa Blvd. At this meeting, all of the families submitted their suggestions for a name. There were 107 names submitted, 5 were considered by a committee as “most suitable” those 5 were Yumesa, Calimesa, Westbourne, Mesa Verde and Beryl. Only one vote was taken, and Calimesa was selected with 22 votes. Dr. Homer Church, a dentist and his wife Margaret, submitted the winning selection “Cali” taken from California and “Mesa” from the Spanish word meaning “hot table” or Flat tabled Land”. The name “Calimesa” was accepted under federal rules and the first post office was established. Bill Bailey was the first post master and operated the office in his grocery store on Calimesa Blvd and Avenue K.
Calimesa Improvement Association and Calimesa Chamber of Commerce
Businessmen in the 1940’s organized the Calimesa Improvement Association which was formed for the purpose of development and improvement of Calimesa and the Community. In 1962 the Calimesa Improvement Association became the Calimesa Chamber of Commerce. The Chamber was a mix of promoting Calimesa, providing community service and being a sounding board of residents’ problems.
In 1963 the Chamber provided the land for the Fire Department that currently sits at 906 Park Avenue. In 1966 they formed th
e County Service Area 46 to provide street lighting. Then in 1968 to 1970 the Chamber was instrumental in forming County Service area 74, which used funds from Riverside County residents’ parcel fees to build and maintain the 11-acre park on Avenue I. A joint powers agreement with the Yucaipa Valley Park and recreation district in San Bernardino County provided the means for the by-county cooperation to complete the park. This park is now in the City of Yucaipa. The group also planned and built the Senior and multipurpose Community Center now known as the Norton Younglove Multipurpose Senior Center. In 1989 the Chamber of Commerce felt it was time to incorporate the community. The Chamber formed a citizen committee, which volunteered their time and resources. The incorporation was the result of citizen effort accomplished without the use or expense of outside consultants. Calimesa became an incorporated City December 1,1990.