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Cañon City sits in a geological bowl surrounded by the Rocky Mountains and the Sangre de Cristo mountain range. Historically, it has been known as the prison capital of the world, with eight-- soon to be nine--state prisons in the area and four federal facilities located 11 miles away in Florence. The first prison in Cañon City was built in 1868, before Colorado became a state, and was opened in 1871. Originally known as the Colorado Territorial Penitentiary, it is currently called the Colorado Territorial Correctional Facility and holds approximately 800 male inmates. Cañon City has grown up around the prisons, and the area's colorful history is defined by daring prison breaks, infamous inmates, such as the Colorado cannibal Alferd Packard, and by the stories of the inmates and employees who have been part of the prison system.

A popular backdrop for numerous movies, Sing Sing, or "the Big House," has been a site of both controversy and reform. The history of Sing Sing dates back to 1825, when warden Elam Lynds brought one hundred inmates to begin construction of the prison "up the river" on the banks of the Hudson. The marble quarry that supplied the building material for the prison was located in an area that was once home to the Sint Sink, a Native American tribe whose name means "stone upon stone." Prison life was dominated by hard labor during the early years. Convicts in striped suits and shackles built the prison with their own hands. With the arrival of warden Lewis Lawes in 1920, Sing Sing became the most progressive prison of its kind. During this time, the New York Yankees traveled up to Sing Sing to play the prison's home baseball team; the prison grounds were landscaped with shrubbery and flower gardens; and the compound grew to include a chapel, mess hall, barbershop, library, and gymnasium. The electric chair was first introduced at Sing Sing in 1891. Julius and Ethel Rosenberg, the first civilians to be found guilty of espionage, were put to death there in 1953. Sing Sing Prison contains rare photographs from the prison archives, the Ossining Historical Society, and a private collection.

On July 1, 1895, under the direction of warden James French, the first federal prison was born. That same year, St. Louis architects Eames and Young went to work drawing up plans for an institution that would house the most notorious offenders in the nation's history. At sunrise on March 1, 1897, 300 inmates and 30 guards marched three miles to the construction site located on the southwest corner of the military reservation. From sunup to sundown seven days a week in the hot Kansas summer to the harsh prairie winters, inmates labored building their new home. Leavenworth's rich history as a gateway to the Old West is second to none. Name a famous figure such as George Armstrong Custer, John Joseph Pershing, Dwight D. Eisenhower, or Colin Powell. They have all graced the streets of this historic community. Equally pick a name of the most notorious criminals. George "Machine Gun" Kelly, Robert F. Stroud, Frank Nash, Frank "the Enforcer" Nitti, and George "Buggs" Moran--they all stopped by to "spend time in Leavenworth."