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In 1842, the Lugo family bought the Rancho San Bernardino Mexican land grant and this became the first fixed settler civilization in the area. The area northwest of current Redlands, astride the Santa Ana River, would become known as Lugonia. In 1851, the area received its first Anglo inhabitants in the form of several hundred Mormon pioneers, who purchased the entire Rancho San Bernardino, founded nearby San Bernardino, and established a prosperous farming community watered by the many lakes and streams of the San Bernardino Mountains. The Mormon community left wholesale in 1857, recalled to Utah by Brigham Young during the tensions with the federal government that ultimately led to the brief Utah War. Benjamin Barton purchased 1,000 acres (4 km2) from the Latter-day Saints and planted extensive vineyards and built a winery.

"The first settler on the site of the present Redlands is recorded to have erected a hut at the corner of what is now Cajon St. and Cypress Ave.; he was a sheep herder, and the year, 1865," reported Ira L. Swett in "Tractions of the Orange Empire." Lugonia attracted settlers; in 1869, Barry Roberts, followed a year later by the Craw and Glover families. "The first school teacher in Lugonia, George W. Beattie, arrived in 1874—shortly followed by the town's first negro settler, Israel Beal."

In the 1880s, the arrival of the Southern Pacific and Atchison, Topeka and Santa Fe Railroads, connecting Southern California to San Francisco and Salt Lake triggered a land boom, with speculators such as John W. North flooding the area now known as the Inland Empire. North and others saw the area, with its hot, dry climate and ready access to water as an ideal center for citrus production. The city of Redlands was soon established by Frank E. Brown, a civil engineer, and E. G. Judson, a New York stock broker, to provide a center (along with North's nearby settlement at Riverside) for the burgeoning citrus industry. They named their city “Redlands” after the color of the adobe soil. So large had the area grown by 1888 that it was decided to incorporate. "A red-letter day in the Annals of Redlands," pronounced Scipio Craig, editor of The Citrograph newspaper, of the November 26 incorporation. The original community of Lugonia was absorbed at this time.

The Redlands Street Railway Company was incorporated on March 22, 1888, acquiring on June 5 a franchise from the San Bernardino County Supervisors dating to December 1887, conveying the right to construct, operate and maintain for a term of 50 years a line of street railways in Redlands, Terracina and vicinity. The initial operations began in June 1889 with a single-track line operating two-mule-team cars, the first street railway company of several to provide service to the community. Electrification and new rails replaced mules in 1899. Most Redlands street railways would pass to the San Bernardino Valley Traction Company in a consolidation on June 3, 1903, and thence to the Pacific Electric in the "Great Merger" of Huntington properties under new ownership by the Southern Pacific Transportation Company on February 8, 1911. Henry E. Huntington, nephew of late Southern Pacific president Collis P. Huntington, had gained control of the four-mile-long streetcar line of the Redlands Central Railway Company in 1908.

The Pacific Electric Railway completed an interurban connection between Los Angeles and San Bernardino in 1914, providing a convenient, speedy connection to the fast-growing city of Los Angeles and its new port at San Pedro, bringing greater prosperity to the town and a new role as a vacation destination for wealthy Angelenos. Redlands was the eastern terminus of the "Big Red Car" system. At its peak, PE operated five local routes in Redlands, with trolleys running to Smiley Heights, and on Orange, Olive, and Citrus Avenues. Pacific Electric interurban service to Redlands was abandoned on July 20, 1936, although PE and Southern Pacific (parent company of PE) provided freight service as far as the Sunkist packing plant on San Bernardino Avenue into at least the 1970s. The abandoned Pacific Electric La Quinta trestle over the Santa Ana River stands today, immediately south of San Bernardino International Airport.

At the turn of the 1900s, Redlands was the "Palm Springs" of the next century, with roses being planted along many city thoroughfares. Some of these plantings would survive as wild thickets into the 1970s, especially adjacent to orange groves where property management was lax. Washingtonia palms (Washintonia robusta) were planted along many main avenues. In fact, Redlands was the first city to have center medians with trees or gardens in between roads. So beautifully kept was the area, with the dramatic mountain backdrops, that for several years the Santa Fe Railroad operated excursion trains along the loop that passed through the orange groves of Redlands and Mentone, across the Santa Ana River, and back into San Bernardino via East Highlands, Highlands and Patton, and advertised as the "Kite Route" due to its multi-sided alignment. The trestle over "the Wash" north of Mentone was carried away during a flood in 1938 and never replaced, the line being truncated there. The Southern Pacific branch line from the San Timoteo Canyon to Crafton was abandoned after the packing house business died. A thru-truss bridge over the Zanja (locally pronounced "Zank-ee") exists today, abandoned in place. Burlington Northern Santa Fe, result of the AT&SF-Burlington Northern merger, applied to abandon its San Bernardino-connected branch line east of downtown Redlands in 2007. A move was made by transit activists to have this branch revitalized as part of the Southern California transit districts, but it came to nothing.

The city has been visited by three Presidents, President McKinley was the first in 1901, followed by President Teddy Roosevelt in 1903 and President William H. Taft. Local landmarks include the A.K. Smiley Public Library, a Moorish-style library built in 1898, and the Redlands Bowl, built in 1930 and home of the oldest continuously free outdoor concert series in the United States. Located behind the Smiley Library is the Lincoln Shrine, the only memorial honoring the "Great Emancipator", the sixteenth president, west of the Mississippi River. Other famous homes include “America’s Favorite Victorian,” the Morey Mansion, on Terracina Boulevard, and the Kimberly Crest House and Gardens, a home museum featured on the PBS series “America’s Castles.” Named after the family that purchased the house, the owners of Kimberly-Clark (makers of paper goods and Kleenex), it is a beautiful mansion set high on a hill overlooking the whole valley. Redlands is still regarded as the "Jewel of the Inland Empire."

According to the United States Census Bureau, the city has a total area of 92.5 km² (35.7 mi²). 91.9 km² (35.5 mi²) of it is land and 0.7 km² (0.3 mi²) of it (0.76%) is water.

As of the census of 2000, there were 63,591 people, 23,593 households, and 16,019 families residing in the city. The population density was 692.2/km² (1,793.1/mi²). There were 24,790 housing units at an average density of 269.8/km² (699.0/mi²). The racial makeup of the city was 73.69% White, 4.31% African American, 0.94% Native American, 5.12% Asian, 0.23% Pacific Islander, 11.33% from other races, and 4.39% from two or more races. Hispanic or Latino of any race were 24.1% of the population. The approximate population is 72,008 (as of March 2008).

There were 23,593 households out of which 33.5% had children under the age of 18 living with them, 50.6% were married couples living together, 13.0% had a female householder with no husband present, and 32.1% were non-families. 26.0% of all households were made up of individuals and 9.2% had someone living alone who was 65 years of age or older. The average household size was 2.61 and the average family size was 3.18.