The Upper West Side was settled by Dutch immigrants in the early and mid-seventeenth century, though not without resistance from the Munsee Indians living on the north end of the island of Manhattan. Warfare with and raids by the Munsees temporarily ended the northward expansion of the Dutch settlers in the 1650s, leaving them with a stretch of land north of the city known as Bloemendal (“Bloomingdale” in English: ‘valley of flowers’).
Originally the Bloomingdale District boundaries applied to the west side of Manhattan from about 23rd Street up to the Hollow Way (modern 125th Street). The main artery of this area was the Bloomingdale Road, which began north of where Broadway and the Bowery Lane join (at modern Union Square) and worked its way northward up to about modern 116th Street in Morningside Heights, where the road further north was known as the Kingsbridge Road. Within the confines of the modern-day Upper West Side, the road passed through areas known as Harsenville (old Bloomingdale Road [Broadway] and 65th St.), Strycker's Bay (Broadway from 86th to 96th Sts.), and Bloomingdale Village (Columbia College & Cathedral of St. John the Divine areas).
As farms and rolling countryside, Bloomingdale was a large producer of tobacco at the beginning of the eighteenth century. In 1703, Bloomingdale Road—later to become the Boulevard, and even later to become Broadway—was built to handle the traffic required by the increasing commerce. By the late eighteenth century, many wealthy merchants had country estates in the relative isolation and wilderness of Bloomingdale, and fine homes and farms dotted the area. In fall of 1776, the war of Independence made its mark on this suburb in the Battle of Harlem Heights, a battle notable only for its strategic unimportance.
In the eighteenth and early nineteenth century, the area hosted some of colonial New York's most ambitious houses, spaced along Bloomingdale Road. The neighborhood became increasingly infilled with smaller, more suburban villas in the first half of the nineteenth century, and in the middle of the century, parts had become decidedly lower class. The Hudson River Railroad line right-of-way, granted in the late 1830s, soon ran along the riverbank, and creation of the Central Park caused many squatters to move their shacks westward into the UWS. Parts of the neighborhood became a ragtag collection of squatters' housing, boarding houses, and rowdy taverns.
Despite its increasingly metropolitan feel, the “West End”, as it was called, remained largely underdeveloped throughout the nineteenth century. It was considered the country—the wilderness. (The Dakota was named so because it was so far away as to be in the Dakotas.) In spite of this, the old name of Bloomingdale Road was being chopped away section by section, and the area further northward including what had been lower Bloomingdale Road was becoming known as Broadway.
By the end of the Civil War, the area of Bloemendal, was assimilated into New York City. In 1868, the city began straightening and grading the section of the Bloomingdale Road from Harsenville north, and it became known as "The Boulevard". It retained that name until the end of the century, when the name Broadway finally supplanted it. This project along with the laying of new sewage systems, and the extension of the elevated railroad up the West Side by way of Ninth Avenue (renamed Columbus Avenue in 1890)—appealed to forward-looking land buyers and developers, who nonetheless remained cautious. Despite the gridding and numbering of the streets in 1811, landholdings and natural obstructions kept innovation largely theoretical until the end of the century. The 1853 creation and construction of Central Park displaced residents of the site, changing the economic face of the West End.
The first gentrification of the UWS came in the late 19th Century. The elevated line up Columbus helped along with Columbia University's relocation to Morningside Heights in the 1890s, using lands once held by the Bloomingdale Asylum. The Upper West Side was built in a boom from 1885 to 1910 as high rises shot up on the West End. Real estate developers invested in such grand projects as the Dakota and the San Remo. The avenues began to acquire their distinct characters: Columbus offered commerce, Amsterdam sported low rent housing and small shops, Riverside Drive (opened in 1880) an alternately elegant and seedy residential park-fronted way, and West End a quiet residential street.
As for “The Boulevard”, it hosted an odd collection of hotels and vacant lots; many of these belonged to developers who continued to await an economic boom that would raise the value of their property and merit construction on a grand scale. The Subway in 1904 improved access and enhanced the appeal of the Upper West Side and apartment buildings proliferated. Eventually, apartment housing pushed out the home-owner oriented row housing which had dominated the rural building trends of the West End for half a century, citifying the West End landscape into the Upper West Side which exists today.
Originally, the neighborhood went only as far south as 65th Street, but with the building of Lincoln Center was stretched to 59th Street. Also, in a modern phase of urban renewal, the rail yards which had formed the Upper West Side's southwest corner were replaced by the Riverside South residential project and a southward extension of Riverside Park. The evolution of Riverside South had a 40-year history, often extremely bitter, beginning in 1962 with the first proposal made by the Penn Railroad itself. The most ambitious proposal, and the one generating the most opposition was Donald Trump's "Television City" concept of 1985, which would have included a 152-story tower. In 1991, civic groups signaled that they were willing to accept a development about 40% smaller in scope than Trump proposed, and things finally started moving. As of 2005 construction is well underway, but still to be resolved is the future of the West Side Highway viaduct over the park area.
The Bloomingdale district was the site for several long-established charitable institutions: their unbroken parcels of land have provided suitably-scaled sites for Columbia University and the Cathedral of Saint John the Divine, as well as for some vanished landmarks, such as the Schwab Mansion on Riverside Drive, the most ambitious free-standing private house ever built in Manhattan.
The name Bloomingdale is still used in reference to a part of the Upper West Side, essentially the location of old Bloomingdale Village, the area from about 96th Street up to 110th Street and from Riverside Park east to Amsterdam Ave. The triangular block bound by Broadway, West End Avenue, 106th Street and 107th Street, although generally known as Straus Park (named for Isidor Straus and his wife Ida), was officially designated Bloomingdale Square in 1907. The neighborhood also includes the Bloomingdale School of Music and Bloomingdale neighborhood branch of the New York Public Library. Adjacent to the Bloomingdale neighborhood is a neighborhood called Manhattan Valley, focused on the downslope of Columbus Avenue and Manhattan Avenue from about 102nd Street up to 110th Street.
Before the 1890’s, when Columbia University relocated from the East Side, Morningside Heights was the location of the Bloomingdale Lunatic Asylum, so the neighborhood was also known as "Asylum Hill."