Sleepy Hollow, New York in the context of "The Great White Way"

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⭐ Core Definition: Sleepy Hollow, New York

Sleepy Hollow is a village in the town of Mount Pleasant in Westchester County, New York, United States, in the New York metropolitan area.

The village is located on the east bank of the Hudson River, approximately 28 miles (45 km) north of Midtown Manhattan in New York City, and is served by the Philipse Manor stop on the Metro-North Hudson Line. To the south of Sleepy Hollow is the village of Tarrytown, and to the north and east are unincorporated parts of Mount Pleasant. The population of the village at the 2020 census was 9,986.

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Sleepy Hollow, New York in the context of Broadway (Manhattan)

Broadway (/ˈbrɔːdw/) is a street and major thoroughfare in the U.S. state of New York. The street runs from Battery Place at Bowling Green in the south of Manhattan for 13 mi (20.9 km) through the borough, over the Broadway Bridge, and 2 mi (3.2 km) through the Bronx, exiting north from New York City to run an additional 18 mi (29.0 km) through the Westchester County municipalities of Yonkers, Hastings-on-Hudson, Dobbs Ferry, Irvington, Tarrytown, and Sleepy Hollow, after which the road continues, but is no longer called "Broadway". The latter portion of Broadway north of the George Washington Bridge/I-95 underpass comprises a portion of U.S. Route 9.

It is the oldest north–south main thoroughfare in New York City, with much of the current street said to have begun as the Wickquasgeck trail before the arrival of Europeans. This then formed the basis for one of the primary thoroughfares of the Dutch New Amsterdam colony, which continued under British rule, although most of it did not bear its current name until the late 19th century. Some portions of Broadway in Manhattan are interrupted for continuous vehicle traffic, including Times Square, Herald Square, and Union Square, and instead used as pedestrian-only plazas. South of Columbus Circle, the road is one-way going southbound.

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Sleepy Hollow, New York in the context of Tarrytown, New York

Tarrytown is a village in the town of Greenburgh in Westchester County, New York, United States, in the New York metropolitan area. It is located on the eastern bank of the Hudson River, approximately 25 miles (40 km) north of Midtown Manhattan in New York City, and is served by a stop on the Metro-North Hudson Line. To the north of Tarrytown is the village of Sleepy Hollow (formerly "North Tarrytown"), to the south the village of Irvington and to the east unincorporated parts of Greenburgh. The Tappan Zee Bridge crosses the Hudson at Tarrytown, carrying the New York State Thruway (Interstates 87 and 287) to South Nyack, Rockland County and points in Upstate New York. The population was 11,860 at the 2020 census.

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