As part of babysitting, I like to explore the city with kids. I grew up in Manhattan and never quite felt that I knew the city well enough. I want the kids I work with to be street wise New Yorkers by their teens, when they won't have a chaperone anymore.

Here is a google map of places I've been with kids.

Other suggestions:

• Any Sephora will let your kids use the make up samples to paint their faces in ridiculous ways (One boy colored his whole nose turquoise with eyeliner). The employees are always etremely nice and there's make up remover to clean their faces when you're done.
• Street fairs. These only happen in the nice weather time of year. They all pretty much have the same stuff available. If you've been to one you've been to all of them. But they are fun to browse.
• Playground Inspector. Bring a notebook and evaluate new playgrounds around the city.
• MTA Adventure. Write a list of directions such as, "Find nearest subway. Take 8 stops north. Find nearest bus stop. Take first bus that comes 5 stops. Walk 4 blocks west." And see where you end up! New York is so densely packed with interesting places and people, there is always an adventure to be found.