Prep work: Make two fliers, one asking students to help and volunteer and one to put in mailboxes in neighborhoods (important info to put on flyer: date, where food is going, what is being collected, student group(s) involved, and a way to donate if they are not home-like leaving a bag of food with their donation outside). Make sure to map out where you put the fliers, I just print out mapquest maps and highlight the areas we reach. Keep these! You will give them to your trick-or-canners the night of Halloween so they know what houses were reached and where to go. Posting fliers: took 1 ½ hours to reach three streets and used 75 fliers. Tell your volunteers to bring a suitcase, remember how much it helps!
Day of event: Have everyone sign in, get people into groups. Each group gets a set of directions and a sign with the flier on it, or some other identifying feature so that people know who you are. Make sure one person in each group has your number and you have theirs in case there is a problem sometime in the night. I like giving each person a glow stick, makes them feel like we care about their safety (which we do, of course). It gets dark about 7:00pm, and you should be done by 9:30pm. Each group can probably get through six streets or more in that time.