Early colonial figures on the island include Wyandanch, Smith, Captain William Kidd, Lionel Gardner, and John Underhill. The western portion of Long Island was settled by the Dutch, while the eastern region was settled by English Puritans from Massachusetts. Long Island was the scene of several witch hunts, including one involving Lionel Gardner in East Hampton.

During the American Revolutionary War, the island was captured by the British early on in the Battle of Long Island, and had a notable loyalist influence, especially in Hempstead. Yankees in northern and eastern parts were more inclined to Rebel sentiments. The island remained a British stronghold until the end of the war. Close ties with England (since colonization and even after independence) may account for the similarities between English accents and the New York Accent, most notably the non-rhotic pronunciation.

19th Century Long Island was rural and agricultural, except along the East River and the country estates of rich city people on the North Shore. Fishermen also plied their trade. Late in the century, the Long Island Railroad began the transformation of some western parts of the island into commuter towns.

Prior to May 4, 1897, the whole of Long Island remained outside the boundaries of New York City as the counties of Queens, Kings and Suffolk. Long Island itself formerly possessed two incorporated cities; the City of Brooklyn and the City of Long Island (in Queens County, now a neighborhood in the Borough of Queens. The name Long Island City harks back to its former status). Both, along with Kings and Queens Counties, were consolidated into “The City of Greater New York” on the May 4th date, with an officially celebrated date of January 1, 1898 (Kings and Queens Counties survive as county names). The eastern most 280 square miles (of Queens County, which rejected consolidation into New York City, formed a separate county. “Nassau”, one of several names by which the island was once known, was revived to represent the newly established county. The figurative “separation” of Brooklyn and Queens from Long Island in popular usage must have begun around this time, since the Battle of Long Island and Long Island City (all nowadays in “The City”) all allude to their geographical location on the island.

When road racing was banned, one of the Vanderbilts opened the Long Island Motor Parkway in 1908 from Kissena to Lake Ronkonkoma. This limited access motor highway was one of the first in the world.

Immigrants spilling over from New York City have made comfortable lives on Long Island. The immigration waves of Southern and Eastern Europe have been pivotal in creating the diversity on Long Island that most other American regions lack. These immigrations are reflected in the large Italian American and Jewish-American populations. Typically the immigrants lived in the more urban western parts of the island, and their children and grandchildren farther east. Late 20th Century immigrants often arrived directly in Nassau County and other suburban areas.

Suburbanization came modestly to Long Island in the early 19th Century when reliable steam ferry service allowed prosperous Wall Street workers to get to new Brooklyn Heights homes in time for dinner. After the American Civil War, streetcar suburbs sprawled out onto the outwash plain of central and southern Kings County, bringing annexation with them. Trolleys also brought workers from other parts of western Queens to Long Island City jobs. After the turn of the century, elevated and subway trains allowed masses of workers to commute to Manhattan jobs from Queens and eastern Brooklyn, which offered cheaper and larger housing but were far beyond reasonable walking distance. The Long Island Railroad played only a limited role in this process, and automobiles had little relevance yet.

In the 1920s and 1930s, Long Island began the transformation from backwoods and farms to the paradigm of the American suburb. With Robert Moses, various parkway projects began to span the island, along with various state parks, Jones Beach being the most famous, “the crown jewel in Moses’ State Park System”. Long Island quickly became New York City’s retreat – with millions of people going to and from the city to the new state parks. As the years wore on, development started to follow the parkways, with various communities springing up along the more traveled routes: (the Southern State Parkway, the Northern State Parkway, and, in the 1960s, the Long Island Expressway).

After World War II, Long Island’s population skyrocketed, mostly in Nassau and western Suffolk, as people who worked and lived in New York City moved out to Long Island in the new developments built during the post-war era boom. The most famous post-war development was the town of Levittown, New York. Positioned along the Wantagh Parkway in the area formally known as Newbridge, (the main traffic corridor has the same name as a homage to what once was), the area became the first place to massively reproduce houses on a grand scale- providing great opportunity for GI’s returning home to start a family.

After the success of Levittown, other areas surrounding fell to “suburban sprawl” and Nassau County became more densely populated than its eastern counterpart, Suffolk County. As the years wore on into the 1960’s and 70’s however, sprawl sent development east of the county line- with areas such as Deer Park, New York and Commack, New York seeing rapid development. As you drive out east along routes such as New York Route 27 (Sunrise Highway) along the south shore or New York State Route 25 (Jericho Turnpike) or New York State Route 25a you will see development start to spread out, even turning back to the potato and sod farms that once were east of towns such as Mount Sinai, New York. Long Island always has a shortage of land, and with real estate prices always on the rise, it is expected to see urban sprawl approach even the farms of Riverhead, New York and beyond. The development of the island is mostly low density, with each house sitting on about 1/2 acre of land out in Nassau and 1-2 acres in Suffolk. The island has a dependency on cars, since mass transit systems aren’t as developed as they are in cities like New York, and many suburbs have no railroad station.

Some urban planners would say that Long Island is only half-suburb, and half-Technoburb. A Technoburb is a community that isn’t urban traditionally, but the population lives in a self sustaining community without a big urban center such as New York City being their main source of jobs. Nassau County is full of New York City commuters and thus the suburban part of the island; Suffolk County contains mostly professionals who work within a 20-mile radius of their homes, in places such as State University of New York at Stony Brook or Computer Associates.

It can be argued, however, that the same is true for dwellers in Nassau County, as it too has opportunities for professionals stemming from its large population as well as universities including Hofstra University, Adelphi University, C.W. Post Campus of Long Island University, and SUNY Old Westbury. A drive to New York City from Eastern Suffolk County could take up to 3 hours with traffic on a normal weekday, thus making it impractical to commute each day, although those living in the western and central communities of the county can quickly arrive in Manhattan via the Long Island Rail Road. In recent years, due to home prices, this dynamic has shifted with more and more Eastern Long Island residents commuting to NYC.

Long Island was hit hard by the September 11, 2001 attacks on the World Trade Center. Many people who live there commute to Manhattan for work every day. In the days after the attacks, it was common to see cars parked for days in the parking lots of Long Island Rail Road stations that belonged to victims of the attacks. On a per capita basis, the village of Garden City lost the largest number of people in the attacks. Also, many of the firefighters called in to assist in evacuation efforts or quelling the underground fires that occurred after the Twin Towers fell were from Long Island.