Brief History of Tarrytown and Sleepy Hollow


First inhabited by the Weckquaesgeek Indians.

1609 – the Hudson River Valley claimed for Holland by Henry Hudson.

1620s – Hudson River Valley settled by the Dutch.

1656 – Wolfert Acker builds a Dutch farmhouse, known as Wolfert’s Roost. (It is later purchased by author Washington Irving.)

1664 – England gained control of the region.

A Dutchman who had Anglicized his name to Frederick Philipse, was awarded 100,000 acres of land by royal charter, becoming New York's greatest "Lord of the Manor." His property extended from Spuyten Duyvil north to the Croton River, and from the Hudson River east to the Bronx River. In what would become Sleepy Hollow he build his Upper Mills.  (His other residence was at Philipse Manor in Yonkers.)

1646 – William Beekman arrived in New York with Peter Stuyvesant. He later married Catharine DeBough. It was their family that would come to own more than half of what later became North Tarrytown (Sleepy Hollow).

1697 – following the destruction of the dam on the Pocantico River amid a flood, a slave of Frederick Philipse told of a dream he had that the dam would never hold until a church was built. The Old Dutch Church built by Philipse still stands on Route 9 in Sleepy Hollow. (It is the oldest extant church in New York.)

1702 – the death of Frederick Philipse. He left the Upper Mills to his son Adolph.

c. 1712 – the house and tavern owned by John and Eliza Van Tassel built. Washington Irving used the house and tavern as a model for the home of one of his characters in The Legend of Sleepy Hollow, Katrina Van Tassel.

the Revolutionary War – Tarrytown was part of the "Neutral Ground," an area of Westchester County lying between the British lines to the south and the American lines to the north. Without the protection of either army, the people were subjected to fierce raids by both sides. British warships cruised up and down the Hudson, often peppered by shots from the shore, while American sloops carrying troops and supplies dodged the men-of-war. Such was the state of affairs when a momentous incident took place in the little village

prior to 1780 – construction of the house of James See; his granddaughter Alice Ackerman, was the wife of the first Tarrytown lighthouse keeper.

1780 (September 23) – Major John Andre was captured by three local militiamen. In his boot were the stolen plans of West Point Andre was carrying to the British for traitor Benedict Arnold. Many historians consider this capture to be a major turning point of the Revolution. (The Historical Society Museum at 1 Grove Street, Tarrytown, Open Tues, Wed, Thurs, Sat 2-4pm, has a wealth of materials related to the capture of Major Andre.)

1780 (October 2) – Major Andre was hanged.

Post-Revolutionary War – the Philipse land was confiscated because of the family’s British sympathies during the Revolutionary War. Sleepy Hollow was then called Beekmantown after the new owners of Philipsburg, the Beekmans. Farming and milling continued for many years on the Manor land.

Tarrytown flourished as an active river port in the post-war period.

1826 – Tarrytown was an idyllic pastoral area.

1835 – author Washington Irving buys the 1656 home of Wolfert Acker, renames it Sunnyside, and spends two years remodeling.

1838 – William Paulding builds a large Gothic Revival residence (now known as Lyndhurst) overlooking the Hudson River.

1839 – ferry service begins on the Hudson River at five cents a ride.

1847 – Pokahoe, the home of James Watson Webb, built. (It later became home of the pathfinder, John C. Fremont.)

1849 – the Hudson River Railroad opened, slowing river traffic. Manufacturing enterprises sprang up.

1853 – a monument to the captors of the British spy John Andre dedicated. It is located at the park along Route 9. William and Mary Taylor donated the land. The actual capture site was about 200 yards east of the monument near the boundary of what later became the two villages.

1859 – the funeral of Washington Irving held at the Christ Episcopal Church where Irving was a church warden and vestryman.

1863 - the draft riot in New York City; rioters head to Tarrytown to burn the storage place for Westchester draft records; Reverend Abel T. Stewart of the Old Dutch Church, Captain Oscar Jones and several local citizens persuaded the rioters to give up their plans.

1864 – Ambrose Kingsland bought Pokahoe, the old home of James Watson Webb.

1865 – Jessie and John C. Fremont buy Pokahoe and live there until 1875. (The home is now on the National Register of Historic Places.)

1870 – the village was incorporated. Jacob Odell was the first mayor. His house on Grove Street later became the headquarters of the Historical Society.

1874 – Sleepy Hollow (then known as North Tarrytown) was incorporated as an entity separate from Tarrytown.

1879 – the statue of John Paulding (one of Andre’s capture) was added to the top of the monument on Route 9.

1880-1960s – railroad tycoon and financier Jay Gould buys Lyndhurst.

1883 – building of the Tarrytown Lighthouse (located off Kingsland Point). Jacob Ackerman was lighthouse keeper from 1883 to 1904.

1886 – William Rockefeller buys the Aspinwal estate and builds Rockwood Hall.

1888 – the famous blizzard of 1888 left 21 inches of snow on the ground.

1893 – a monument to area Revolutionary War Soldiers erected on Battle Hill.

1893 – John D. Rockefeller Sr., president of Standard Oil, came to Tarrytown/Sleepy Hollow. His grandsons via John D. Rockefeller Jr. Were David, Nelson, Winthrop, Laurance and John D. Rockefeller III.

1896 – the John and Eliza Van Tassel property became the site for the first Washington Irving High School and their old house was demolished.

1897 – the first run of the White Plains/Tarrytown Trolley.

1899 – construction of the automobile factory (designed by Stanford White) on the Kingsland property.

turn of the century – palatial mansions dotted the hills overlooking the Hudson.

1900 – Carrollcliffe, the Castle at Tarrytown, built for General Howard Carroll, son of a Civil War General.  It was designed by noted New York Architect Henry Killburn and place on top of a ridge overlooking the area (and easily seen from US 287). The Castle was built in a style reminiscent of Norman fortification in Wales, Scotland and Ireland.  Later it was known as the Axe Castle when it was owned by E.W. Axe & Co.  Now it is a luxury inn and restaurant.  .

1902 – John D. Rockefeller Sr.’s country retreat, the Parsons-Wentworthhouse in Pocantico Hills, burns down and plans were made to build the Kykuit mansion.

1906 – a photo taken this year shows Ambrose Kingsland’s gazebo on Kidd’s Rock (named for Captain Kidd who supposedly traded with Frederick Philipse.)

1913 – construction of Kykuit completed.

1914 – Orchard Street was a growing hub of business in Tarrytown.

1916 – Singer/entertainer Elsie Janis (Elsie Bierbower originally) bought the Philipse Manor Upper Mills. During the war she was known as the "Sweetheart of the AEF" (the American Expeditionary Force) because of her entertainment of the troops abroad. After WWI she and her mother restored the Manor house.

Sleepy Hollow was home to the famous "Stanley Steamer" automobile factory.

General Motors built a huge assembly plant in Sleepy Hollow. At the peak of its operations the plant employed over 4,000 workers.

1923 – death of William Rockefeller. His property eventually becomes a public park.

1928 – John D. Rockefeller Jr. backed the building of the five-story Van Tassel apartment building to overcome the shortage of apartments for the families of Chevrolet workers.

1929 – the last run of the White Plains/Tarrytown Trolley.

WWII – the Axe Castle in Tarrytown was used by Civil Defense plane spotters.

WWII – the General Motors plant in North Tarrytown was converted to the manufacture of airplane parts.

following WW II – clusters of single-family homes replaced large estates.

1950s – building of the Tappan Zee Bridge, ending ferry service. Construction of the New York State Thruway and Tappan Zee Bridge accelerated the growth of Tarrytown/Sleepy Hollow.

1960s – Anna Gould, Jay Gould’s daughter, left Lyndhurst to the National Trust for Historic Preservation.

1960s – F. W. Woolworth Company store razed.

1965 – the Tarrytown Lighthouse was decommissioned. It is now on the National Register of Historic Places.

1996 – the village of North Tarrytown officially changed its name from North Tarrytown to Sleepy Hollow.

1996 – the General Motors plant closed. The village plans to limit construction on this prime river front area to residential and light commercial buildings and water-related enterprises such as marinas.


Sleepy Hollow Chamber of Commerce. "History of the Tarrytown/Sleepy Hollow Area.."

Historical Society, Inc, Serving Tarrytown and Sleepy Hollow. 1997. Images of America: Tarrytown and Sleepy Hollow. Charleston, SC: Arcadia Press.