Route: All of Broadway (NY)

Run the whole length of Broadway in Manhattan. Either direction works, with the Manhattan-side of the Broadway Bridge being one point, and the statue of the Bull the other, though probably a little more epic to go north to south. A classic New York route that takes you through Inwood, Washington Heights, Hamilton Heights, Harlem, Columbia, Upper West Side, Columbus Circle, Midtown, Times Square, Herald Square, Garment District, Madison Square, Flatiron, Union Square, NYU, NoHo, Soho, Tribeca and the Financial District.