Founding through Civil war (1790-1865)

1 Dolley Madison, first-lady spy

First lady Dolley Madison established an observation post on the White House roof in 1814 to watch for the approaching British army. While fleeing to avoid capture, she saved the Gilbert Stuart portrait of George Washington before the White House was set ablaze.

White House, 1600 Pennsylvania Ave. NW

2 Winder Building Signal Corps cupola

Winder Building | PHOTO: Library of Congress

One of the highest points in Washington at the time of the Civil War, the cupola of the Winder Building was chosen by the Union Signal Corps for point-to-point visual communications with nearby camps and forts.

600 17th St. NW

3 Lowe balloon launch site

Launching of Lowe's balloon. | PHOTO: Library of Congress

Professor Thaddeus S. C. Lowe conducted the first aerial combat reconnaissance in our nation’s history from a tethered balloon west of Washington. On June 24, 1861, he observed and reported Confederate Cavalry activity.

Fort Taylor Park, North Roosevelt Street and Ridge Place, Falls Church, Virginia

4 Mansion House Hotel

Sarah Emma Edmonds. | PHOTO: University of Michigan

Sarah Emma Edmonds claimed to have donned multiple disguises and personas as a Union spy, including a young man, Irish peddler, Southern gentleman and African American laundress. Later, she worked as a nurse at the Mansion Hotel, which had been converted to a Union hospital.The hotel, once located in front of the Carlyle House, has since been demolished.

121 N. Fairfax St., Alexandria, Virginia

5 Kirkwood House Hotel

Sketch of the Kirkwood House.

The Kirkwood House Hotel was at times home to Benjamin Franklin Stringfellow, a spy of many disguises, who has been called the “Confederate James Bond.” George Atzerodt, a conspirator in Abraham Lincoln’s assassination, also stayed at the hotel; he was assigned to kill Vice President Andrew Johnson, who lived at Kirkwood House, but he lost his nerve, drank heavily and fled.

12th Street and Pennsylvania Avenue NW

6 Gardner's Gallery

Gardner Gallery | PHOTO: INSCOM

Alexander Gardner’s photographs provide an invaluable historical record of the Civil War, but at the time they were also used to identify spies and for cartography. His photographs of Ford’s Theatre following Lincoln’s assassination are among the first crime scene photographs.

511 7th St. NW

7 Old Capitol Prison

Old Capitol Prison | PHOTO: National Archives

Sprawling across the site of what is now the Supreme Court building, the Old Capitol Prison held two of the most infamous and flamboyant Confederate spies, Belle Boyd, who was arrested many times and released, increasing her fame, and Rose O’Neal Greenhow, whose information aided the Confederacy in its victory at the First Battle of Bull Run.

1st and East Capitol St. NE

8 Surratt boarding house

Mary Surratt's boarding house. | PHOTO: Library of Congress

Southern sympathizer Mary Surratt ran a boarding house that served as a safe house and base of operations for conspirators in Lincoln’s assassination.

604 H St. NW

Post-Civil War to World War II (1866-1945)

1 Van Deman offices

Maj. Gen. Ralph Van Deman | PHOTO: INSCOM

Maj. Gen. Ralph Van Deman deserves the title “father of modern military intelligence”. As America entered World War I, he built the country’s first professional military intelligence organization in the Old Executive Office Building.

639 17th St. NW

2 A. Mitchell Palmer residence

Attorney General A. Mitchell Palmer's residence after the explosion. | PHOTO: Library of Congress

In an act of World War I era terrorism, an anarchist blew himself up while bombing the home of Attorney General A. Mitchell Palmer in June 1919, causing extensive damage.

2132 R Street NW

3 Bellevue Hotel

Drawing of The Bellevue Hotel. | PHOTO: 'A Death in Washington', Gary Kern and the New York Journal-American

In 1941, Soviet intelligence defector Walter Krivitsky was found dead in his room at the Bellevue Hotel, now known as the Hotel George, from a single gunshot to the head. Although ruled a suicide, suspicions still linger that Soviet intelligence directed the killing.

15 E St. NW

4 East Building, Office of Strategic Services headquarters

East Building, Office of Strategic Services headquarters. | PHOTO: Central Intelligence Agency

The East Building on Medicine Hill was headquarters to the OSS and later the first home of the Central Intelligence Agency. Today the building is listed on the National Register of Historic Places for its clandestine history.

23rd and E streets NW

5 Vint Hill

Several original buildings remain at the former Vint Hill top secret cryptographic school and signals-intercept site, although in recent years the area has been redeveloped into a residential and business community.

4263 Aiken Drive, Warrenton, Virginia

6 Vichy French Embassy

Former Vichy French Embassy.

At the Vichy French Embassy, World War II spy Amy Elizabeth Thorpe, wearing only a necklace and high heels to throw off a guard, aided a safe-cracking operation to steal diplomatic codes.

2129 Wyoming Ave, NW

7 Arlington Hall

Arlington Hall during World War II. | PHOTO: INSCOM

Arlington Hall Junior College for Women became the location of America’s World War II code-breaking programs. The majority of the 10,000 workers were young women with an aptitude for math.

4000 Arlington Blvd., Arlington, Virginia

8 Mayflower Hotel

Mayflower Hotel.

Over the decades, the prestigious and popular Mayflower Hotel has offered quiet venues for clandestine meetings involving Nazi saboteurs, Soviet agents and American spies such as CIA agent Aldrich Ames, who spied for Russia, and government scientist Stewart Nozette, who attempted to sell classified information to the Mossad.

1127 Connecticut Ave. NW

Cold war espionage (1946-1991)

1 British Embassy diplomats and Soviet spies

Harold “Kim” Philby's home on 4100 Nebraska Ave. NW.

Harold “Kim” Philby, the senior MI6 British liaison officer to the FBI and the CIA, was secretly a Soviet spy and leader of Britain’s Cambridge Spy Ring. Another member of the ring, diplomat Guy Burgess, was a frequent guest in Philby's home. Both men worked at the British Embassy.

3100 Massachusetts Ave. NW (embassy), 4100 Nebraska Ave. NW (Philby house)

2 Air America

Air America, a CIA proprietary company, operated one of the world’s largest airlines during the 1950s and 1960s, with 20,000 employees and 200 aircraft. Its pilots flew hazardous missions, landing at remote jungle airfields and dropping supplies under enemy fire.

918 16th St. NW

3 Pullman House

The mansion was acquired by Russia in 1913 and served as the Russian and Soviet Embassy until becoming the Russian ambassador's residence in 1994. Soviet and Russian espionage operations were planned and run from here.

1125 16th St. NW

4 Steuart Motor Company

Steuart Motor Company. | PHOTO: Jacqueline Dupree, JDLand.com

One of the most unlikely clandestine sites in Washington, the Steuart Motor Company building also housed the CIA’s National Photographic Interpretation Center. Not so subtly, perhaps, guards armed with machine guns surrounded the building when unprocessed top-secret film from U-2 photos of Cuban missile sites was delivered.

5th and K streets NW

5 Exchange Saloon

During the 1970s, the Exchange Saloon was a capital hot spot for swingers. The husband-and-wife spy team of Karl and Hana Koecher of the Czech intelligence service Statni Bezpecnost spent time at the saloon looking for potential agents.

1719 G St. NW

6 Hanssen signal site

Mugshot of Robert Hanssen.

Robert Hanssen, an FBI agent turned Russian spy, used the Foxstone Park entrance sign as a signal site to communicate with his Soviet handlers. When a horizontal piece of adhesive white tape appeared on the sign, they knew that their spy had loaded the dead drop, code-named ELLIS, at the first footbridge inside the park.

1910 Creek Crossing Rd. NE, Vienna, Virginia

7 Aldrich Ames site

Aldrich Ames being arrested. | PHOTO: Central Intelligence Agency

Ames, a career CIA officer, spied for nearly 10 years while living in an upper-middle-class house that had been purchased with money received from the KGB. When driving to his CIA office in 1994, he was boxed in after stopping at an intersection a few blocks from his home. Pulled from behind the wheel, he was thrown over the hood of his beloved maroon Jaguar, handcuffed and arrested.

North Quebec Street and Nelly Custis Drive, Arlington, Virginia

8 Jonathan Pollard meeting site

Meeting site in Dumbarton Oaks.

In a scene worthy of a John le Carré novel, Jonathan Pollard, a former U.S. intelligence analyst and spy for Israel, conducted a clandestine meeting with his Israeli handler on a bench in the gardens of the Dumbarton Oaks Research Library and Collection. In the idyllic setting, the two negotiated the pay Pollard would receive for classified documents.

1703 32nd St. NW

Today's spies (1992-2016)

1 CIA memorial

Memorial outside CIA's campus. | PHOTO: Central Intelligence Agency

A simple public memorial outside the CIA’s campus pays tribute to the two CIA officers murdered by Pakistani terrorist Mir Aimal Kansi on Jan. 25, 1993.

CIA headquarters, McLean, Virginia

2 Cuban Embassy

Cuban Embassy on 16th St. | PHOTO: Slowking4/Wikimedia

After the United States and Cuba broke diplomatic relations, Cuba maintained limited official status in its former embassy as an “interest section” operated through the Swiss government. Cuban intelligence officers met with reporters and others in the second-floor Hemingway Lounge and Bar.

2630 16th St. NW

3 Ana Montes residence

Mugshot of Ana Montes.

Nicknamed the “Queen of Cuba” for her research as an analyst at the Defense Intelligence Agency, Montes showed uncommon discipline in her 17-year career as a Cuban spy. But an error in tradecraft -- failure to wipe incriminating evidence from her computer -- exposed covert communications with Cuban intelligence and led to her arrest in 2001.

3039 Macomb St. NW

4 Stanislav Gusev operation

Surveillance image of Stanislav Gusev by the State Department building. | PHOTO: Federal Bureau of Investigation

Exactly how Russian intelligence implanted a microphone and transmitter in a chair rail in the State Department remains a mystery. The operation was exposed in 1999 after FBI agents observed Gusev, a Russian technical officer, repeatedly repositioning his vehicle in different parking places nearby to remotely control the bug.

2201 C St. NW

5 Tysons-Pimmit Library

Tysons-Pimmit Library.

By using computers at public libraries, Brian Patrick Regan sought anonymity while planning espionage activities. Showing care for security, he devised a sophisticated private cipher that baffled investigators seeking evidence against him. But he was eventually tripped up in 2001 by his spelling errors.

7584 Leesburg Pike, Falls Church, Virginia

6 Final resting place

Arlington National Cemetery.

Many American intelligence officers are buried at Arlington National Cemetery, among them: OSS chief William “Wild Bill” Donovan; code-breakers William and Elizebeth Friedman; CIA director Richard Helms; and U-2 pilot Francis Gary Powers.

Arlington Veteran Cemetery, Memorial Drive, Arlington, Virginia

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