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. 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 located slightly north of Lakeside (30 minutes from downtown San Diego), and is home to a restful as well as stylish hotel, a respected golf course and top of the mark buffet. The legal gambling age at the property is 18. The spokesman is singer Kenny Rogers.
Lakeside has been a choice site for filming, such as the TV series "Renegade".
Lakeside has two large reservoirs, El Capitan and San Vicente.
