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Southold

Located in the northern tip of Suffolk County, the town of Southold has a population of 21,968 citizens. It was colonized in 1640 and is generally considered to be the first English settlement on Long Island.

Cutchogue

A hamlet in Suffolk County, NY, Cutchogue has a population of 3,349 residents. The hamlet covers a total area of 10.2 square miles, with only 0.4 square miles being water, and the rest of 9.7 being all land.

Mattituck

Mattituck is a hamlet in Suffolk County, New York, with a population of nearly 4,300 residents according to the 2010 census. It derives its name from the Algonquian name for Great Creek, and covers a total area of 9.3 square miles.

New Suffolk

A hamlet located in the town of Southold, New Suffolk has a population of only 349 residents according to the 2010 census. The hamlet covers an area of just 0.6 square miles, with only 0.04 square miles being water, and the rest land.

Greenport

Roslyn is a village located in Nassau County, on the North Shore of Long Island with a population of approximately 2,770 according to the 2010 census.

Orient

First settled in 1682, and with a population of only 2,197 residents, the village of Greenport sits at the north fork of Long Island. Thanks to it's strong fishing and whaling industry, Greenport was considered a major trading port in the area.

East Marion

East Marion is a hamlet in the town of Southold in Suffolk County, New York with a population of 926 according to the 2010 census. It covers an area of only 2.4 square miles, with only 0.2 square miles being water.

Laurel

Laurel hamlet is located is located in Suffolk County, and has a population of about 1400 residents, covering a total area of 3.1 square miles. Most of the hamlet is located within the town of Southold, with a small portion of it located in the town of Riverhead.

Jamesport

Jamesport, known for its quaint downtown area littered with antique shops and fine dining restaurants, is a hamlet in the town of Riverhead, in Suffolk County. It has a population of almost 2000 residents, and covers a total area of 4.5 square miles.

Peconic

Having a very small population of only 683 residents, Peconic takes its name from the native word for "nut tree". It covers a total area of 3.5 square miles, with only 0.1 square miles being water.