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1. New York City
There's just something about New York in the fall that makes you feel like Blair Waldorf, you know? New York in the summer can be stifling; New York in the winter can be too crowded. But fall? The Christmas decor is just going up, Central Park looks like a leaf-peeper's dream and there are so many events you can hit: the New York Marathon, festivals upon festivals and -- duh -- the Macy's Thanksgiving Day Parade! Flocking to a city in the fall isn't the obvious choice, but trust in the autumnal presence of Manhattan.