It works the same way in Maps.app: when you tap and hold for a second or two the app drops a pin there.
I’ll attach a piece of code here (I need LongPress to work on annotations and it doesn’t work in this code). Please consider helping.
MKPinAnnotationView* pinView = [[[MKPinAnnotationView alloc] initWithAnnotation:annotation reuseIdentifier:MeAnnotationIdentifier] autorelease];
pinView.canShowCallout = NO;
UILongPressGestureRecognizer *longPressGesture = [[UILongPressGestureRecognizer alloc] initWithTarget:self action:@selector(showCountdown:)];
[pinView addGestureRecognizer:longPressGesture];
[longPressGesture release];
You can use a UILongPressGestureRecognizer. You can specify the time needed for it to fire. Dropping a pin there however is a matter of properly placing and animating an image, but giving you code for that would be doing pretty much all work for you instead of simply helping you with your problem?