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The area that is now Silver Spring has been inhabited by various American Indians for 10,000 years. Prior to European colonization, the area was inhabited by the Piscataway, an Algonquian-speaking people. The Piscataway may have established a few small villages along the banks of Sligo Creek and Rock Creek.

The Blair, Lee, and Jalloh and Barrie families, three politically active families of the time, are irrefutably tied to Silver Spring's history. In 1840, Francis Preston Blair, who later helped organize the modern American Republican Party, along with his daughter, Elizabeth, discovered a spring flowing with chips of mica – believed to be the now-dry spring which is visible at Acorn Park. Blair was looking for a site for his summer home to escape the heat of Washington, D.C., summers. Two years later, Blair completed a 20-room mansion he dubbed Silver Spring on a 250-acre (1 km²) country homestead. In 1854, Blair moved to the mansion permanently. The house stood until 1954.

By 1854, Blair's son, Montgomery Blair, who became Postmaster General under Abraham Lincoln and represented Dred Scott before the United States Supreme Court, built the Falkland house in the area.

By the end of the decade, Elizabeth Blair married Samuel Phillips Lee, third cousin of future Confederate leader Robert E. Lee, and gave birth to a boy, Francis Preston Blair Lee. The child would eventually become the first popularly elected Senator in United States history.

During the American Civil War, Abraham Lincoln visited the Silver Spring mansion multiple times. During some of the visits he relaxed by playing town ball with Francis P. Blair's grandchildren.

In 1864, Confederate Army General Jubal Early occupied Silver Spring prior to the Battle of Fort Stevens. After the engagement, fleeing Confederate soldiers razed Montgomery Blair's Falkland residence.

At the time, there was a community called Sligo located at the intersection of the Washington-Brookeville Turnpike and the Washington-Colesville-Ashton Turnpike (now named Georgia Avenue and Colesville Road). Sligo included a tollhouse, a store, a post office, and a few homes. The communities of Woodside, Forest Glen, and Linden were founded after the Civil War. These small towns largely lost their separate identities when a post office was established in Silver Spring in 1899.

By the end of the 19th century, the region began to develop into a town of size and importance. The Baltimore & Ohio Railroad's Metropolitan Branch opened on April 30, 1873, and ran from Washington, D.C. to Point of Rocks, Maryland, through Silver Spring.

The first suburban development appeared in 1887 when Selina Wilson divided part of her farm on current-day Colesville Road (U.S. Route 29) and Brookeville Road into five- and ten-acre (20,000- and 40,000 m²) plots. In 1892, Francis Preston Blair Lee and his wife, Anne Brooke Lee, gave birth to E. Brooke Lee, who is known as the father of modern Silver Spring for his visionary attitude toward developing the region.

The early 20th century set the pace for downtown Silver Spring's growth. E. Brooke Lee and his brother, Blair Lee I, founded the Lee Development Company, whose Colesville Road office building remains a downtown fixture. Dale Drive, a winding roadway, was built to provide vehicular access to much of the family's substantial real estate holdings. Suburban development continued in 1922 when Woodside Development Corporation created Woodside Park, a neighborhood of 1-acre (4,000 m²) plot home sites built on the former Noyes estate in 1923. In 1924, Washington trolley service on Georgia Avenue (present-day Maryland Route 97) across B&O's Metropolitan Branch was temporarily suspended so that an underpass could be built. The underpass was completed two years later, but trolley service never resumed. It would be rebuilt again in 1948 with additional lanes for automobile traffic, opening the areas to the north for readily accessible suburban development.

Takoma-Silver Spring High School, built in 1924, was the first high school for Silver Spring. The community's rapid growth led to the need for a larger school. In 1935, when a new high school was built at Wayne Avenue and Sligo Creek Parkway, it was renamed Montgomery Blair High School. (The school remained at that location for over six decades, until 1998, when it was moved to a new, larger facility at the corner of Colesville Road (U.S. Route 29) and University Boulevard (Maryland Route 193). The former high school building became a combined middle school and elementary school, housing Silver Spring International Middle School and Sligo Creek Elementary School.) The Silver Spring Shopping Center (built by developer Albert Small) and the Silver Theatre (designed by noted theater architect John Eberson) were completed in 1938, at the request of developer William Alexander Julian. The Silver Spring Shopping Center was unique because it was one of the nation's first retail spaces that featured a street-front parking lot. Conventional wisdom held that merchandise should be in windows closest to the street so that people could see it; the shopping center broke those rules (the shopping center was purchased by real estate developer Sam Eig in 1944 who was instrumental in attracting large retailers to the city).

Prior to the 1950's, Silver Spring was known as a sundown town due to influential land owners. The North Washington Real Estate Company designed 63 acres to be white-only, written in its deeds to prevent the sale of land to anyone else. No legislative action was taken to prevent this until 1967 (where such an ordinance was illegal until Shelley v. Kramer, 1948).

By the 1950s, Silver Spring was the second busiest retail market between Baltimore and Richmond, with the Hecht Company, J.C. Penney, Sears, Roebuck and Company, and a number of other retailers. In 1954, after standing for over a century, the Blair mansion "Silver Spring" was razed and replaced with the Blair Station Post office. In 1960, Wheaton Plaza (later known as Westfield Wheaton), a shopping center several miles north of downtown Silver Spring opened, and captured much of the town's business. The downtown area soon started a long period of decline.

On December 19, 1961, a two-mile (3.2 km) segment of the Capital Beltway (I-495) was opened to traffic between Georgia Avenue (MD 97) and University Boulevard East (MD 193). On Monday, August 17, 1964, the final segment of the 64-mile (103 km) Beltway was opened to traffic, and a ribbon-cutting ceremony was held near the New Hampshire Avenue interchange, with a speech by then-Gov. J. Millard Tawes, who called it a "road of opportunity" for Maryland and the nation.

Washington Metro rail service into Washington, D.C. helped breathe life into the region starting in 1978 with the opening of the Silver Spring station. The Metro Red Line was built following the alignment of the B&O Metropolitan Branch, with the Metro tracks centered between the B&O's eastbound and westbound mains. The Red Line heads south to downtown DC from Silver Spring, running at grade before descending into Union Station. By the mid-1990s, the Red Line continued north from the downtown Silver Spring core, entering a tunnel just past the Silver Spring station and running underground to three more stations, Forest Glen, Wheaton and Glenmont.

Nevertheless, the downtown decline continued in the 1980s, as the Hecht Company closed in 1987 and opened a new store at Wheaton Plaza; furthermore, Hecht's added a covenant forbidding another department store from renting its old spot. City Place, a multi-level mall, was established in the old Hecht Company building in 1992, but it had trouble attracting quality anchor stores and gained a reputation as a budget mall, anchored by Burlington Coat Factory and Marshalls, as well as now-closed anchors AMC Theatres, Gold's Gym, Steve and Barry's, and Nordstrom Rack. JC Penney closed its downtown store—downtown's last remaining department store—in 1989, opening several years later at Wheaton Plaza. In the late 1980s and early 1990s, developers considered a shopping mall and office project called Silver Triangle, with possible anchor stores Nordstrom, Macy's, and JC Penney, but no final agreement was reached. Shortly thereafter, in the mid-1990s, developers considered building a mega-mall and entertainment complex called the American Dream (similar to the Mall of America) in downtown Silver Spring, but the revitalization plan fell through before any construction began because the developers were unable to secure funding. However, one bright spot for downtown was that the National Oceanographic and Atmospheric Administration (NOAA) consolidated its headquarters in a series of 4 new high-rise office buildings near the Silver Spring Metro station in the late 1980s and early 1990s.

Another notable occurrence in Silver Spring during the 1990s was a 1996 train collision on the Silver Spring section of the Metropolitan line. On February 16 of that year, during the Friday-evening rush hour, a MARC commuter train bound for Washington Union Station collided with the Amtrak Capitol Limited train and erupted in flames on a snow-swept stretch of track in Silver Spring, leaving 11 people dead.

The Maryland State Highway Administration started studies of improvements to the Capital Beltway in 1993, and have continued, off and on, examining a number of alternatives (including HOV lanes and high-occupancy toll lanes) since then.

At the beginning of the 21st century, downtown Silver Spring began to see the results of redevelopment. Several city blocks near City Place Mall were completely reconstructed to accommodate a new outdoor shopping plaza called "Downtown Silver Spring." New shops included national retail chains such as Whole Foods Market, a 20-screen Regal Theatres, Men's Wearhouse, Ann Taylor Loft, DSW Shoe Warehouse, Office Depot, and the now-closed Pier 1 Imports, as well as many restaurants, including Panera Bread, Red Lobster, Cold Stone Creamery, Fuddruckers, Potbelly Sandwich Works, Nando's Peri-Peri, and Chick-fil-A. A Borders book store was a popular spot until it closed when the chain went out of business; it was replaced by H&M. In addition to these chains, Downtown Silver Spring is home to a wide variety of family-owned restaurants representing its vast ethnic diversity. As downtown Silver Spring revived, its 160-year history was celebrated in a PBS documentary entitled Silver Spring: Story of an American Suburb, released in 2002. In 2003, Discovery Communications completed the construction of its headquarters and relocated to downtown Silver Spring from nearby Bethesda. However, Discovery, Inc. announced in 2017 that they would be relocating to New York City. The reason for this move, according to Discovery, was to operate close to their "ad partners on Madison Avenue," "investors and analysts on Wall Street," and their "creative and production community," said their CEO, David Zaslav, in an email to employees. 2003 also brought the reopening of the Silver Theatre, as AFI Silver, under the auspices of the American Film Institute. Development continues with the opening of new office buildings, condos, stores, and restaurants. In 2015–16, the long-struggling City Place Mall underwent a complete renovation, had its name changed to Ellsworth Place, and brought in new tenants, including TJ Maxx, Ross Dress for Less (a re-opening original tenant), Michaels, Forever 21, and Dave & Buster's. The restoration of the old B&O Passenger Station was undertaken between 2000 and 2002, as recorded in the documentary film Next Stop: Silver Spring. In 2005, Downtown Silver Spring was awarded the silver medal of the Rudy Bruner Award for Urban Excellence

Beginning in 2004, the downtown redevelopment was marketed locally with the "silver sprung" advertising campaign, which declared on buses and in print ads that Silver Spring had "sprung" and was ready for business. In June 2007, The New York Times noted that downtown was "enjoying a renaissance, a result of public involvement and private investment that is turning it into an arts and entertainment center".

In 2007, the downtown Silver Spring area gained attention when an amateur photographer was prohibited from taking photographs in what appeared to be a public street. The land, leased to the Peterson Cos., a developer, for $1, was technically private property. The citizens argued that the Downtown Silver Spring development, partially built with public money, was still public property. After a protest on July 4, 2007, Peterson relented and allowed photography on their property under limited conditions. Peterson also claimed that it could revoke these rights at any time. The company further stated that other activities permitted in public spaces, such as organizing protests or distributing campaign literature, were still prohibited. In response, Montgomery County Attorney Leon Rodriguez said that the street in question, Ellsworth Drive, "constitutes a public forum" and that the First Amendment's protection of free speech applies there. In an eight-page letter, Rodriguez wrote, "Although the courts have not definitively resolved the issue of whether the taking, as opposed to the display, of photographs is a protected expressive act, we think it is likely that a court would consider the taking of the photograph to be part of the continuum of action that leads to the display of the photograph and thus also protected by the First Amendment." The incident was part of a trend in the United States regarding the blurring of public and private spaces in developments built with both public and private funds.

In 2008, construction of the long-planned Intercounty Connector (ICC), which crosses the upper reaches of Silver Spring, got under way. The highway's first section opened on February 21, 2011; the entire route was completed by 2012.

In July 2010, the Silver Spring Civic Building and Veterans Plaza opened in downtown Silver Spring.

In May 2019, The Peterson Companies, owners of the Downtown Silver Spring development, announced a $10 Million renovation of the area that will include public art and a new outdoor plaza, featuring green space.

Note: For the 2010 Census the boundaries of the Silver Spring CDP were changed reducing the land area by approx. 15%. As a result, the population count for 2010 shows a 6.6% decrease, while the population density increases 11%.

As enumerated in the 2010 census, there were 71,452 residents, 28,603 total households, and 15,684 families residing in the Silver Spring CDP. The population density was 9,021.7 people per square mile (3,485.5/km²). There were 30,522 housing units at an average density of 3,853.8 per square mile (1,488.9/km²). The racial makeup of the community, as defined by the U.S. Census Bureau, for residents who self-identified as being members of "one race," was 45.7% "White," 27.8% "Black or African American," 0.6% "American Indian and Alaska Native," 7.9% "Asian," 0.1% "Native Hawaiian and Other Pacific Islander," and 13.2% "Some Other Race" (SOR). 4.8% of the CDP's residents self-identified as being members of "two or more races." "Hispanic or Latino" residents "of any race" comprised 26.3% of the population. Like much of the Washington metropolitan area, Silver Spring is home to many people of Ethiopian ancestry.

There were 28,603 households, out of which 27.1% had children under the age of 18 living with them, 37.6% were married couples living together, 11.9% had a female householder with no husband present, and 45.2% were non-families. 33.6% of all households were made up of individuals living alone, and 16.5% had someone living alone who was 65 years of age or older. The average household size was 2.49 and the average family size was 3.21.

In the census area, the population was spread out, with 21.4% under the age of 18, 9.4% from 18 to 24, 37.1% from 25 to 44, 23.8% from 45 to 64, and 8.4% who were 65 years of age or older. The median age was 33.8 years. For every 100 females, there were 94.9 males, and for every 100 females age 18 and over, there were 92.2 males.

The median income for a household in the census area was US$71,986, and the median income for a family was US$84,136. Males had a median income of US$46,407 versus US$49,979 for females. The per capita income for the area was US$32,181. 15.0% (±4.9%) of the population and 13.3% (±4.3%) of families were below the poverty line. Twenty-one percent (±9.1%) of those under the age of 18 and 23.6% (±10.6%) of those 65 and older were living below the poverty line.^{[citation needed]}

For the 2000 census, there were 76,540 people, 30,374 households, and 17,616 families residing in the census area (if all areas with the "Silver Spring" address are included, the population swells to around 250,000). The population density was 8,123.6 people per square mile (3,137.2/km²). There were 31,208 housing units at an average density of 3,312.3 per square mile (1,279.1/km²). The racial makeup of the community was 46.61% White, 28.07% Black American, 0.44% Native American, 8.22% Asian, 0.06% Pacific Islander, 11.55% from other races, and 5.04% from two or more races. Hispanic or Latino people of any race consist of 22.22% of the population.

There were 30,374 households, out of which 29.4% had children under the age of 18 living with them, 40.8% were married couples living together, 12.5% had a female householder with no husband present, and 42.0% were non-families. Thirty-two-point six percent (32.6%) of all households were made up of individuals, and 7.8% had someone living alone who was 65 years of age or older. The average household size was 2.50 and the average family size was 3.21.

The ages of the population were varied, with 23.0% under the age of 18, 9.3% from 18 to 24, 37.0% from 25 to 44, 21.2% from 45 to 64, and 9.6% who were 65 years of age or older. The median age was 34 years. For every 100 females, there were 93.4 males. For every 100 females age 18 and over, there were 89.5 males.

The median income for a household in the census area was $51,653, and the median income for a family was $60,631. Males had a median income of $38,124 versus $36,096 for females. The per capita income for the area was $26,357. 9.3% of the population and 6.4% of families were below the poverty line. 11.7% of those under the age of 18 and 9.7% of those 65 and older were living below the poverty line.