Great Hurricane of 1938
The Great Hurricane of 1938 is legendary for the destruction it wreaked on eastern Long Island, creating islands and inlets and changing the entire landscape. City-data.com

Hurricanes are a part of life in the southeastern U.S., but the mid-Atlantic states and New England have far less experience with the storms. It's especially rare for a hurricane to strike New York City directly; more often, they skirt the city and hit the eastern reaches of Long Island and Cape Cod. Since 1851, only five hurricanes have struck within 75 miles of New York City -- Gloria in 1985, Belle in 1976 and unnamed storms in 1938, 1894 and 1893, according to data from the Weather Channel -- although the edges of a handful of others have caused measurable damage here. However, if Hurricane Irene sticks to its projected path, New York's luck could run out.

It's difficult to objectively quantify the destructiveness of hurricanes, since many factors contribute, but here are six of the worst to affect the New York area.

1. New England Hurricane, 1938

When it made landfall on Long Island on Sept. 21, 1938, this became the first major hurricane since 1869 to hit any part of New England directly. More than 70 years later, it remains the deadliest in regional history, with 60 people killed in New York, all on Long Island. (The hurricane claimed up to 800 lives in total, destroyed nearly 60,000 homes and caused $306 million in damage as it moved north from the Bahamas to southern Quebec.) By the time it hit New York, the hurricane had weakened to Category 3 from its peak Category 5 status, but the devastation was such that even a decade later, some buildings and trees were still visibly damaged.

Long Island bore the brunt of the storm, to the point that the very landscape changed. Part of Westhampton Beach in Suffolk County was wiped out altogether, accounting for 29 of the 60 casualties, and a theater there was inundated by water, sweeping about 20 more people out into the Atlantic Ocean. Montauk became an island for a time thanks to the storm surge, and the island where the Cedar Point Lighthouse stands became connected to the mainland at Cedar Point County Park. The entire Shinnecock Inlet on the southern shore of Long Island was also a product of the surge.

New York City itself didn't receive a direct hit, but the damage was still considerable. The storm surge from the East River flooded three blocks of Manhattan, and witnesses claimed the Empire State Building even swayed. Sustained winds ranged from 75 miles per hour to more than 100 miles per hour, and there was a nearly citywide power outage.

2. Hurricanes Carol and Edna, 1954

These two storms hit the region within less than two weeks of each other, causing serious cumulative damage. The Category 3 Hurricane Carol came first, on Aug. 30, blasting eastern Long Island with winds up to 120 miles per hour. The storm surge was severe, and it flooded the main highway in Montauk, forcing the evacuation of several hundred families and making travel between eastern and western Long Island essentially impossible. Fortunately for the rest of the New York area, the storm was very small in size in spite of its intensity, and it barely affected areas west of Fire Island as it passed by. The estimated death toll was 68.

Hurricane Edna was only Category 1 when it passed over New York on its way to Cape Cod on Sept. 11, 1954, but it still managed to kill 20 people, according to data from the American Meteorological Society. Again, eastern Long Island suffered the worst damage, as Edna dumped 9 inches of rain and flooded Montauk Point, forcing the evacuation of several hundred families there. The combined damage from the two storms was about $500 million, mostly from Hurricane Carol.

3. Norfolk and Long Island Hurricane, 1821

The Norfolk and Long Island Hurricane was remarkable for its location: it's one of only two hurricanes in recorded history that made landfall in New York City itself, and the only one in at least the past 500 years (historians believe the other storm hit New York sometime between the 13th and 15th centuries). It hit Jamaica Bay in Queens on Sept. 3, 1821. The storm surge was spectacular, reaching 13 feet at its peak and flooding Manhattan all the way from Battery Park to Canal Street. There wasn't much rain, but winds were extremely high, although the Saffir-Simpson Hurricane Scale didn't exist at that time to categorize them. Long Island was also affected, although not as severely as Manhattan; several ships were blown away and at least 17 people drowned.

4. Great September Gale, 1815

This hurricane happened so long ago that it wasn't even called a hurricane at the time. However, it had geological effects similar to those of the New England Hurricane of 1938 in that it permanently changed the physical landscape of Long Island. The inlet that separates Long Beach from the Rockaways in southeastern Brooklyn was the product of the storm surge, and north of Long Island, the surge reached 11 feet. In places, mostly in more northern parts of New England, winds topped 130 miles per hour. At least 38 people died throughout the affected areas, and the damage reached more than $12 million, adjusted for inflation.

5. Hurricane Gloria, 1985

Gloria was the most recent hurricane to make landfall here, hitting western Long Island in late September 1985 with winds up to 115 miles per hour. At the time, the director of the National Hurricane Center called it the storm of the century, although it didn't cause as much devastation as it could have. Altogether it caused eight deaths and nearly $1 billion in damage in 1985 dollars, with one death and $300 million in damage in New York. Several piers on Long Island were swept away, and nearly 700,000 people in New York lost power for up to a week and a half. There wasn't significant flooding; the brunt of the damage came from Gloria's high winds.

6. Hurricane Agnes, 1972

Agnes was only a Category 1 hurricane when it struck just west of New York City, but it brought more destruction than many far stronger hurricanes: more even than the Category 4 Hurricane Betsy, which hit the Bahamas, Florida and Louisiana in 1965. It killed close to 130 people total, including 24 in New York, and caused $3 billion in damage ($702 million in New York). The worst devastation, however, was in Pennsylvania.