Lakeside began when the land that it is on was purchased by the El Cajon Valley Land Company. It started as a resort town, based around the once renown automobile race course at Lindo Lake that Barney Oldfield made famous in 1907. It was once home to the historical Lakeside Hotel, a destination for health and relaxation reached by long day's buggy ride or train.
It has long held the title of a "cowboy town" or "rodeo town" due to the rural settings, the large percentage of ranches and the abundant horse ownership in the area. Lakeside has also been acclaimed for its almost "Mayberry" feel to it. It is home to an 8-acre (32,000 m2) permanent rodeo facility known world wide as Lakeside Rodeo grounds. What is unique about the rodeo grounds is that it is manned by a totally volunteer group and has been for over 47 years with the premise being support of the Youth of Lakeside. The proceeds from any facility rentals are donated to local youth through sports, service and education grants. The premier rodeo of the Southern CA season is the PRCA sanctioned Lakeside Rodeo (occurs the last weekend in April annually) and it draws over 20,000 observers to the arena. The Lakeside Optimist annually host the Bulls Only Rodeo (July) at the facility and work on behalf of the local youth. Many social and service groups are very active in this town(VFW, Elks, Optimist, Soroptimist, 4H, FFA, Boys and Girls Club, Boys Scouts and Girls Scouts, Peacebuilders, PLAY, youth soccer, baseball and football teams, BMX) and the Historical Society works hard to keep the Americana feel to the Maine Street. One of the major focuses of the community has been the establishment of a River Park along the meandering river bed, where equestrians and walkers alike can enjoy pristine, safe paths and native animals can reside.
Other noticeable qualities about Lakeside are the residents' pride, deep love and respect for the rural area, and the fortunate lack of growth in any economic sector. As the years have passed, the area has also changed with diversity in ethnic make-up. Instead, many cultures have moved outward from the inner city San Diego without fear, in search of the stability that this rugged little town offers. The U.S. Navy maintains two large housing sites for military dependents in the town.
The Barona Casino is slightly north of Lakeside (30 minutes from downtown San Diego), and is home to a hotel, golf course and buffet. The legal gambling age at the property is 18. The spokesman is singer Kenny Rogers. Other Native American casinos are nearby as well such as the Viejas casino is located a few miles east of Lakeside on I-8.
Lakeside has been a choice site for filming, such as the TV series "Renegade".
Lakeside has two large reservoirs, El Capitan and San Vicente.
According to the United States Census Bureau, Lakeside has a total area of 6.1 mi² (15.7 km²). 5.7 mi² (14.8 km²) of it is land and 0.3 mi² (0.9 km²) of it (5.62%) is water.
As of the census of 2000, there were 19,560 people, 6,849 households, and 5,150 families residing in the CDP. The population density was 1,320.3/km² (3,420.7/mi²). There were 7,047 housing units at an average density of 475.7/km² (1,232.4/mi²). The racial makeup of the CDP was 89.83% White, 0.75% African American, 1.10% Native American, 1.27% Asian, 0.28% Pacific Islander, 3.28% from other races, and 3.49% from two or more races. Hispanic or Latino of any race were 11.52% of the population.
There were 6,849 households out of which 39.4% had children under the age of 18 living with them, 57.9% were married couples living together, 12.4% had a female householder with no husband present, and 24.8% were non-families. 18.7% of all households were made up of individuals and 7.3% had someone living alone who was 65 years of age or older. The average household size was 2.83 and the average family size was 3.22.
In the CDP the population was spread out with 29.0% under the age of 18, 8.4% from 18 to 24, 30.8% from 25 to 44, 21.7% from 45 to 64, and 10.1% who were 65 years of age or older. The median age was 35 years. For every 100 females there were 96.5 males. For every 100 females age 18 and over, there were 94.2 males.
The median income for a household in the CDP was $48,910, and the median income for a family was $55,336. Males had a median income of $41,258 versus $29,375 for females. The per capita income for the CDP was $20,100. About 6.9% of families and 8.5% of the population were below the poverty line, including 10.4% of those under age 18 and 9.5% of those age 65 or over.
In the state legislature Lakeside is located in the 36th Senate District, represented by Republican Dennis Hollingsworth, and in the 77th Assembly District, represented by Republican Joel Anderson. Federally, Lakeside is located in California's 52nd congressional district, which has a Cook PVI of R +9and is represented by Republican Duncan Hunter.