I think Voodooo doll has some good ideas, but I know I'd never ever ever never ever go around the block in cosplay. Cosplay goes from house to car to event, and that's it for me. Maybe a drive-through or something, but that's it until I get to the convention. Being alone in costume is far more nerve wracking than being among fellow cosplayers.
Smaller conventions and photoshoots are the best way to go.
facebook page // nh/mass cosplay events
Next event: In-CON-Ceivable
COSPLAYS IN PROGRESS
Umbreon (Pokemon gijinka) - Constructing
Gaius (Fire Emblem: Awakening) - Buying stuff
Vaati (LoZ Minish Cap) - Planning
Soren (Fire Emblem: Radiant Dawn) - Constructing