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New Haven, CT (Population: 124,791)

New Haven, Connecticut, located on the northern end of the Long Island Sound, may be the first planned community in the United States. Founded in 1638, the city consisted of a grid of streets creating what is now known as the Nine Squares, which make up modern downtown New Haven. The city's nickname the Elm City comes from the canopy of mature elm trees that resulted from the first public planting of trees in America. Perhaps best known as the home of Yale University, New Haven is also home to the New Haven Green, a 16-acre park and recreation area which was created by the original Puritan settlers.

While the claims of the first hamburger sandwich and the first American pizza are both disputed, New Haven hails itself as being at least one of the first cities in the country to have served these dishes. In the early 20th century, New Haven was the new home of many Italian immigrants; New Haven style pizza is called apizza and is made on a coal or wood-fired brick oven and is known for its paper-thin crust. There are over 120 restaurants within two blocks of New Haven Green, many of which are highly-rated, well known dining establishments. For vegetarians, Claire's Corner Copia claims to be the oldest vegetarian restaurant in the country.

New Haven Green is a popular site for summer concerts and festivals, including New Haven Symphony Orchestra and the New Haven Jazz Festival. Free concerts are offered throughout the year through the Yale School of Music. Yale University is affiliated with many of the museums and theatrical events that take place in the area.