Any route you choose will have to take the NYC Runners Marathon into account. There will be times when as either a cyclist or a pedestrian, you will not be permitted to cross the route. Similarly, the route and crossing it, will be closed to cars, making the adjacent streets much more crowded.

The roughest part will be the stretch along 4th Ave between 20th and 39th Streets. There's the harbor, 3rd Ave, 4th Ave, 5th Ave and Greenwood Cemetary. Both 3rd and 5th Aves will be clogged with cars and 4th Ave will be clogged with runners.