Top 16 Small Cities in New York

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2. Greenport

Not to be confused with another town named Greenport in the same state, Greenport, New York in Suffolk County on Long Island is a small, charming town that’s beautiful and full of terrific food, according to local “foodies” who swear the town has some of the best food anywhere in the country.

The population of the town is rather small at 2,197, according to statistics on the census, but tourists often visit the town to take part of the adventurous “Foodie Scavenger Hunts,” as detailed on North Forker. According to the town’s official website, Greenport was first settled by Europeans in the middle of the 17th century.

Colonists living in New Haven, Connecticut decided to cross Long Island Sound and take up residence in what would become Greenport. The town’s website goes on further to describe the early popularity with the town’s work with oysters as there were several processing plants in the vicinity during the first half of the 20th century.

Today, one of the best-named restaurants in town pays homage to that history with the name of “The Frisky Oyster.” Owing to the town’s closeness to the water, visitors who come to eat at the town’s terrific restaurants get to enjoy nicely warm temperatures in the summer and winters that aren’t too terribly cold.

The Weather Channel suggests highs just reach 80 in the summer and usually sit around the upper 30s during the days in the winter. However, the lows tend to stop at the mid-20s during the nights, so the weather is far from frigid.

The prices for homes in the area do reflect the nice geographic location of Greenport and some homes situated directly on the water tend to have a value of close to $1 million. Towns in the village’s tiny city center are often gorgeously historical and might be anywhere from 150 to 200 years old.

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