My Favorite:

Annapolis City Dock

It's located at the Historic Annapolis Foundation, on the second floor. The view changes every 10 seconds, so when I go to Annapolis, I set my machine at home to capture the pictures. I stand where I know I'll be seen by the webcam, make note of the time, and when I get home, VOILA! I have a free portrait of myself on City Dock!

Wincing Devil
UberNerd