During Virginia's colonial period, Rosslyn's shoreline included a landing for Awbrey's ferry, which transported travelers to and from Georgetown.

Known primarily for its gambling halls, pawnshops, saloons, brothels and unsavory inhabitants, the community failed to attract much development other than the Arlington Brewery, which became a Cherry Smash soft drink bottling plant after Prohibition went into effect.

Eventually, spurred by the real estate potential that the arrival of electric trolleys in the 1890s inspired, developers and reformers ousted Rosslyn's more unsavory elements in the early 20th century.

They organized under the name "Good Citizen's League" and nominated Captain Crandal Mackey as the Commonwealth's Attorney to fight corruption.

[3] The area around Rosslyn remained dangerous, especially at night on the Falls Church Turnpike, now U.S. Route 29, Langston Boulevard.

A short way past Rosslyn heading west was Dead Man's Hollow, near today's intersection with Spout Run.

Arlington County widened Rosslyn's major streets to accommodate the increased motor vehicle traffic that this new development would bring.

The Arlington County government has since announced plans to dismantle some or all of the bridges that carry the skywalks over Rosslyn's broad streets.

[7] During the Watergate scandal of the early 1970s, "Deep Throat" (W. Mark Felt) passed information to Washington Post reporter Bob Woodward in the middle of the night in an underground parking garage at 1401 Wilson Boulevard in Rosslyn.

Both the company and the newspaper occupied two high-rise silver-colored towers, built in the early 1980s, which adjoin each other at 1000 and 1100 Wilson Boulevard.

In the same year, the ABC-affiliate in Washington, D.C., WJLA-TV, "ABC 7", moved their main studios into the space in Rosslyn previously occupied by USA Today.

[18] In 2017, the international food and beverage company Nestlé S.A. announced that it would move its U.S. corporate headquarters from California to this building.

In order to make the area more walkable, Rosslyn's elevated walkways and other urban peculiarities are planned to be demolished or modified, along with lanes being removed or reversed.

[21][22] The Annual NoVa International Jewish Film Festival is held each spring in Rosslyn and other Virginia locations.

[27] The annual US FreedomWalk Festival, started in 2000, draws walkers from around the world each Fall for a weekend of walks in Rosslyn and nearby areas.

[31] The Netherlands Carillon in Rosslyn is a set of 50 bells housed in a 12-story tower between Arlington National Cemetery and the Marine Corps War Memorial.

Vamoose Bus provides daily service from 1801 N Lynn Street in Rosslyn to Penn Station/Madison Square Garden in Midtown Manhattan in New York City.

One can also cross the Francis Scott Key Bridge at the end of Lynn Street and pick up the unpaved C&O Canal towpath or the paved Capital Crescent Trail in Washington.