@Expendable there's a lot of great stuff in there, and our sportsball mascot is definitely the Grim, although I think the school's main sport is baseball.
So a baseball field or two is a must.
I've already spawned a second character idea, a gargoyle named Stanley. Bums cigarettes, sits in on classes in the back.
Some more town ideas, mostly in the streets in front of the school's gates.
A fancy restaurant with bar as close as possible to the main gate.
A local drug store. (should be two or three of them)
A diner (may be two at opposite ends).
A movie theater/playhouse - midnight showings of Rocky Horror Picture Show on Fridays and Saturdays. Bring Your Own Toast.
A Hot dog/ Sausage on a Bun Hut
A jewelry store
A small store selling stuffies and beanie babies.
A bicycle shop
A discount store selling cheap clothes, school supplies, home goods, has a small luncheon counter in the bottom level and paid toilets (don't forget to bring your dime)
A couple of churches
Ethnic restaurants (Chinese, Indian, Mexican)
Pizza parlors
Ice cream place
Comic/game store (already mentioned I'm sure)
Used book store
Magazine/newspaper shop (sells coffee, soda, candy bars, packaged honey rolls, snack cakes and hand pies)
Local candy store
Movie Palace - video rental with large private booths upstairs with large, boxy rear-projection tvs and a vcr, you can rent one of the booths for groups up to eight people, movie concessions stand. Notorious make-out place.
Tobacconist shop
Crazy Dave's Tattoo parlor - famous for the demon tattoo, but you must bring your own demon.
Bars
Army/Navy Surplus (sells messenger bags and backpacks)
Thrift shops/goodwill.
A small mall, possibly outside of town, with various common stores and restaurants. (Malls are parasites that feed off of cities and towns)
Trinket stores (candles, occult goods)
Stationery stores (one sells fancy journals, pens, framed sayings, etc. while one's further out with office supplies, typewriters, cubical settings)
Fancy kitchen store.
Lumber yards and hardware stores (do you know how hard it is to scrape together a coffin at 3 AM?)