[2] A disconnected section of Riverside Drive begins at the Henry Hudson Parkway's Dyckman Street exit in Inwood, ending at Broadway.

[14] Despite the structure's utilitarian role as a highway, it was also a strong symbol of civic pride, inspired by America's late 19th-century City Beautiful movement.

[26] The 191 acres (0.77 km2) of land in what is now Riverside Park between 72nd and 125th streets were originally inhabited by the Lenape people, but by the 18th century were used for farms by the descendants of European colonists.

[46] One publication described Riverside Drive as "one of the most beautiful and picturesque in the world",[51][52] and The New York Times wrote that the avenue's mansions "glittered like a wedding cake" by the 1890s.

[55] In January 1897, state lawmakers proposed extending Riverside Drive northward to the Boulevard Lafayette, with a viaduct above Manhattan Valley from 122nd to 134th Street.

[16] The viaduct's engineers requested in June 1898 that the approaches be made of granite rather than sandstone, which would add $80,000 to the cost;[68] the city's comptroller opposed the change.

[21][74] The chief engineer of the city's highways departments reported in April 1901 that the Manhattan Valley Viaduct was completed except for filling and electrical work.

[94] To pay for the construction of the extension, the Riverside Drive and Parkway Commission proposed charging local residents $1.5 million, though the high cost was controversial.

[96] John C. Rodgers, who helped build the section from 145th to 158th streets, later sued the city for delaying the road's completion by four years; the suit was not resolved until 1930.

[102] John F. Ahearn, Manhattan's borough president, began requesting bids for the construction of Riverside Drive from 158th Street to Spuyten Duyvil, Bronx in March 1909.

[111] Olmsted and Arnold W. Brunner recommended in 1913 that Riverside Drive be extended north to the Bronx, with a new viaduct connecting 155th Street and the Boulevard Lafayette.

[121] The New York City Board of Estimate voted down a resolution in 1921 to build a parallel roadway to Riverside Drive between 155th and 175th streets, within Hamilton Heights, at a cost of $7 million.

[122] The next year, borough president Julius Miller submitted plans to build a road, known as Riverside Drive West, between 155th and 177th streets for $2.791 million; this would serve as a bypass of the existing roadway.

[124] The city's proposal to widen Riverside Drive required the acquisition of land, including a portion of the Columbia University Irving Medical Center's site along the Hudson River.

For instance, city controller Charles L. Craig wanted the Board of Estimate to build a parallel roadway above the West Side Line,[142] and one local organization requested that the avenue's sparsely-used bridle path be converted into a children's play area.

[162] The city government also submitted plans in mid-1936 for a $7 million upgrade to the existing section of Riverside Drive between St. Clair Place (at the southern end of the Manhattan Valley Viaduct) and Dyckman Street.

[165] The section of Riverside Drive between the George Washington Bridge and Dyckman Street was incorporated into the northbound roadway of Henry Hudson Parkway.

[170] Conversely, the developer Charles V. Paterno predicted that the avenue would again become an upscale residential corridor because of its location and the construction of the Henry Hudson Parkway and George Washington Bridge.

[176] The city government began reconstructing the viaduct from 153rd to 155th streets in March 1959; the project involved increasing the roadway's width from 45 to 59 feet (14 to 18 m), replacing the steel frame, and constructing new sidewalks.

[191] City workers began excavating shafts for the tunnel in 1970, which required the construction of temporary footpaths, but local residents protested the project because it was too noisy.

[194] When a section of the Henry Hudson Parkway was entirely closed for repairs in January 1974,[195] drivers were detoured onto Riverside Drive, and a no-parking restriction was enacted between 72nd and 79th streets.

[196][197] In response, the adjacent section of Henry Hudson Parkway was partly reopened as a reversible lane in September 1974,[198] but this failed to decrease congestion on Riverside Drive.

[199] In addition, double-decker buses began running on the M5 route along Riverside Drive in 1976, requiring the relocation of several traffic lights and wires, as well as the removal of tree limbs.

[224] Paul Willen, who had led one of the civic groups that opposed the original plan, had suggested extending Riverside Drive "to make such an abandoned lump of a place feel like New York again".

[239] In 2005, the retaining wall of Castle Village collapsed onto the northern section of Riverside Drive and the northbound lanes of the Henry Hudson Parkway.

[253] At the end of the 19th century, the eastern side of Riverside Drive consisted of a series of luxuriously finished rowhouses interspersed with free-standing mansions set in large lawns.

[260] Riverside Drive includes several notable row houses as well, which were generally occupied by the middle class,[261] though comparatively few townhouses remain standing.

[262] There are several rowhouses with stepped gables at 74–78 Riverside Drive, a relative rarity on the avenue, where most row houses were designed in the Beaux-Arts style.

[27] The southern portion of Riverside Drive is lined with many Art Deco, Beaux-Arts, and Renaissance Revival apartment buildings, mostly housing cooperatives;[2] in particular, the section south of 96th Street is primarily occupied by luxury co-ops.

[49] A reporter for the same newspaper said in 2018 that Riverside Drive "links a half-dozen historic neighborhoods and a parade of attractive architecture while offering open space across nearly its entire western flank".