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In 1846, the Hudson River Railroad (later the West Side Line and Hudson Line) was built along the waterfront, connecting New York City to Albany.
Similar development in the Upper West Side was slower to come: by 1865, only West 76th and 86th Streets had been completed and opened.
In 1865, Central Park commissioner William R. Martin put forth the first proposal for a riverside park along the Hudson River.
The first segment of Riverside Park was acquired in 1872 by condemning lots for a cost of $7.25 million, or over $80,000 per acre ($200,000/ha) for each of the 119 acres (48 ha) in the original park.
Olmsted wrote in 1873 that Riverside Park "presented great advantages as a park because the river bank had been for a century occupied as the lawns and ornamental gardens in front of the country seats along its banks.
A temporary tomb for the late United States president Ulysses S. Grant was built at Claremont Hill in 1885, since Grant had said he wanted to be buried in New York City.
These residents formed an organization called the West End Avenue Association, which in 1888 published a booklet titled West End Avenue: Riverside Park in the City of New York extolling the park's benefits.
Additionally, paths between 72nd and 79th Streets were laid out in 1891.
In November 1893, a compromise was reached that would allow for the shore to be used for parkland while still allowing access to docks, and two months later, the park commissioners adopted plans to build docks at 79th and 96th Streets.
However, in an 1893 article, The New York Times mentioned that "but a small portion of the land thus acquired has been improved so as to be capable of public use." At the time, Riverside Park did not include the shorefront.
By 1895, paths had been laid out between 96th and 120th Streets.
Another structure built in the park was Columbia University's Gould Boathouse, constructed at 115th Street in 1896.
However, in 1898, construction commenced on an ornate viaduct carrying Riverside Drive across the valley to 135th Street.
By 1902, plans were made to extend the park's border north to 155th Street.
Another proposal, for a new boathouse for the Motor Boat Club, was vetoed by mayor George B. McClellan Jr. in 1906.
In 1906, there was an effort to expand Riverside Park by adding the piece of land bounded by Riverside Drive, Claremont Avenue, and 116th and 122nd Streets.
As early as 1909, there were plans to expand the West Side Line to six tracks within Riverside Park, though this was heavily opposed.
One prominent group to form during this time was the Women's League for the Protection of Riverside Park, formed in 1916 to advocate recreational uses within the park.
Another initiative that aided the redevelopment of Riverside Park was the closure of one of the garbage dumps in 1923.
In June 1929, the city voted to approve a plan that would build the parkway above the tracks, but not on the waterfront.
Work between 72nd and 79th Streets was underway when parks commissioner Robert Moses was appointed in 1934.
Having achieved its goal of rebuilding Riverside Park, the Women's League disbanded in 1937.
In addition, plans for a new boat basin at 149th Street were announced in 1939.
The West Side Improvement project was completed by 1941.
A monument to the Warsaw Ghetto Uprising, first proposed in 1947, was never realized due a lack of funding and opposition from city officials.
By 1962, a new children's playground was proposed between 102nd and 106th Streets, to be dedicated to the philanthropist Adele Rosenwald Levy.
In 1970 a writer for The New York Times observed that the northern part of the park, in western Harlem, was in worse condition than the original park near the Upper West Side and Morningside Heights.
In 1971, officials proposed converting the West Side Elevated Highway and Henry Hudson Parkway into Westway, a six-lane interstate highway connecting the George Washington Bridge and the Brooklyn–Battery Tunnel, which would have resulted in the condemnation of portions of Riverside Park.
The Friends of Riverside Park organization was formed in March 1979, initially working to plant new trees and stop deterioration of existing trees.
By 1979, NYC Parks was restoring retaining walls and making plans to rehabilitate several playgrounds.
The city indicated in 1983 that it planned to refurbish parts of the park, especially the section between 97th and 110th Streets, at a cost of $910,000.
The Westway plan was abandoned altogether by 1984.
In 1987, fourteen area cooperatives combined to create the Riverside Park Fund to raise money for maintenance.
Facing great opposition and hobbled by his weak financial position, Trump agreed in 1990 to adopt a new plan for the site put forward by six civic groups.
Starting in 1992, NYC Parks restored the retaining wall within Riverside Park between 98th and 120th Streets.
The 28-acre (11 ha) Riverbank State Park was built atop the plant, opening in 1993.
By 1994, the Riverside Park Fund was conducting various projects including landscaping, the installation of new playgrounds, and the restoration of existing facilities.
In November 1998, the first phase of the new Riverside Park South started, having been designed by Thomas Balsley & Associates.
A dog run was proposed for the Morningside Heights section of the park in 1998, but was canceled after opposition.
Phase 1, a 7-acre (3 ha) section from 72nd to 68th Streets, was opened just over two years later in January 2001.
Phase 3, opened in August 2006, stretches from 65th Street to 62nd Street on the waterfront.
Phase 4 opened in 2007 along the waterfront from 62nd to 57th Streets.
In 2015, after a quarter-century of planning, construction started on a new pedestrian bridge connecting Hamilton Heights to Riverside Park at 151st Street, replacing a tunnel and a long staircase.
However, NYC Parks has approved interim and final designs for those two sections; construction of the interim park started in August 2016.
After some delays, the bridge opened in 2017.
Also in 2017, NYC Parks released a master plan for Riverside Park.
The first section opened in 2019.
In 2019, The New York Times observed that following every rainstorm, water tended to pool on the roof of the Freedom Tunnel and other locations due to the three-tiered topography of the park, and that the tunnel's retaining wall was leaking.
The cost as submitted to the New York City Board of Estimate was $11 million (equivalent to $205 million in 2020), of which $6 million would go toward the railroad tunnel alone (equivalent to $112 million in 2020).
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