At the time the El Cajon Valley Land Company began to promote Lakeside as a town site in 1886, there were few inhabitants in the area.  It was 1859 when the Ames family moved into the Los Coches area.  There was the Pedrorena Rancho near what is now the center of town.  In 1869, the Ferry Ranch house was constructed in Lakeside Farms and the Ben Hill house was built on what is now Willow Road and Wildcat Canyon Road.  Other ranchers moved into the area -- the Kuhner's in 1881, the Philbrooks  in the early 1880's.  Although construction of the Flume was in progress in 1883, it wasn't completed until 1889 and the only means for watering gardens and small orchards was windmills.

Small businesses began to spring up -- Beamer's Stable and Blacksmith's Shop, a boarding house that later became the general store, a butcher shop, a school was started, and to take care of the spiritual needs of the new town, in 1895 a church was built on Maine Street.  San Diego's population grew from 7,500 in 1886 to 25,000 by November 1, 1887.  With the building of the Inn in 1887 and the construction of the railroad, Lakeside became a resort town.  Twenty-six miles of this railroad line became the most traveled in San Diego County.  Governor Waterman became its sole owner in 1890.  Before the railroad, there was a daily stage between Lakeside and San Diego which took four hours for the trip.
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1882

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1910

In the July 9, 1937, issue of the Lakeside Farmer, Dick Henderson made these observations: "My first recollection of the Lakeside Hotel is finding shelter there from a heavy shower, which caught my mother and a lady friend and I up in El Monte and got us well soaked before we reached shelter.  Mother was taking up a 'pre-emption claim' on Boulder Creek, above the diverting dam, and she and I spent a winter there.  Six months residence was required to get title.  That was 50 years ago.  Lakeside was the center of activity of this region.  It is much different from Lakeside in 1898, with its paved highway and autos standing on both sides; but as Otto Marcks remarked a few days ago, there was lots of business in the old days."

Outlying areas formed their own personality.  Foster was a small town, completer with post office and depot.  There was Dexter Valley, El Monte, Riverview, Winter Gardens, Lakeside Farms, Eucalyptus Hills, and Lakeview.  There were no boundaries to guide you, but you knew when you were there.