Recent archaeological excavations near Wicker's Creek have recently established that Dobbs Ferry was inhabited at least four thousand years ago, before the first European contact.

The Weckquaesgeek Indians, a branch of the Mohican tribe of the Algonquin nation, later inhabited Dobbs Ferry. Due to Dobbs Ferry's close proximity to the Hudson, fresh fish was available in addition to game and various crops such as planted pumpkins and beans that sustained the inhabitants of this area.

The Philipse family owned this area for several generations. However, during the Revolution, the third lord of the Philipse Family remained loyal to the King and was forced to flee. His land was confiscated by the State and sold mostly to former tenant farmers who had supported the patriot cause. Many historic properties, such as Washington Irving's Sunnyside Historic Site were part of the original Philipseburg Farm.

During the Revolution, this area was the ground for many battles. On September 30, 1778, at Edgars Lane, American militia ambushed and destroyed an eighty-man Hessian patrol. In 1781, the Dobbs Ferry shoreline and Sneden's Landing were fortified to prevent the British fleet from disabling American and French supply lines. American fire from the Dobbs Ferry Redoubt sank the warship HMS Savage that had been attacking American supply sloops off Tarrytown. Also, original manuscripts of General George Washington state that Washington met at Dobbs Ferry with French allies the Comte de Rochambeau and the Comte de Grasse at this location to plan the Battle of Yorktown that ended the war with Great Britain. Historians have long debated whether this meeting took place at present day Dobbs Ferry or at the ferry location directly opposite on the Hudson River. However, a monument stands in Dobbs Ferry at Livingston Manor, the site of the claimed 1781 meeting.

During the 1830s New York City was in dire need of a fresh water supply to combat the steady rise of disease and to fight numerous fires that often engulfed large tracts of businesses and homes. Construction of an unprecedented magnitude began in 1837 under the expertise of John Bloomfield Jervis. The proposed plan called for a 41-mile aqueduct and dam to be built in order to run water from the Croton River to New York City. The Croton Aqueduct was completed in 1842 and passed through the center of what is now the Dobbs Ferry central business district. Press: Old Croton Aqueduct State Historic Park for more information.

The growth of this area was further stimulated by the advent of the steamboat and later in the 1880s by the building of the railroad. The advent of the railroad had a large impact on the growth of Dobbs Ferry. The railroad stimulated growth and industry in most towns running along the banks of the Hudson River.

By the end of the 19th century, the region had attracted wealthy New Yorkers who established large estates. The newspaper tycoon Henry Villard settled within Dobbs Ferry. The homes of the Vanderbilts, the Goulds, Rockefellers, and others were built nearby.

In the last half of the nineteenth century, Westchester's proximity to New York City, its transportation systems, and its available labor force attracted many manufacturing concerns, particularly along the Hudson River. Peekskill and Croton continued to be centers for the iron industry and Dobbs Ferry along with its neighboring towns continued to prosper and grow.