"Quirky" has always been one of my favorite genres of TV series and movies, and such things often tend to be set in quirky towns. Mostly the quirkiness of the towns has to do with the quirkiness of the characters who live there, but the towns themselves can sometimes have some inherent quirkiness. So, here is a list of some of the quirky towns with which I'm familiar (mostly in TV series), and maybe a few quirky locations besides towns. (No doubt there are places I'm forgetting that I'd include here if I remembered them, as well as some places I'm not entirely sure qualify as "quirky" or not.)

Films

Beaverfield, (unknown state); from Werewolves Within

Mumford, Oregon; from Mumford

Spectre, (Alabama, maybe?); from Big Fish

(unknown town, unknown state); from Edward Scissorhands

Radio

Lake Wobegon, Minnesota; from A Prairie Home Companion

Television

30 Rockefeller Plaza, New York City, New York; from 30 Rock (Just one TV studio where everyone is kinda quirky.)

99th Precinct, Brooklyn, New York; from Brooklyn Nine-Nine (Just one floor of one police precinct, but I do consider it quirky.)

Chatswin, New York (presumably); from Suburgatory

Cicely, Alaska; from Northern Exposure (One of my all-time favorite quirky towns.)

Coeur d'Coeurs, (unknown state); from Pushing Daisies

Deepwater, Florida; from Maximum Bob

East Peck, South Carolina; from Trial & Error

Eureka, (unknown state); from Eureka

Evening Shade, Arkansas; from Evening Shade

Greendale Community College; from Community (Not a town, but the college definitely fits the trope.)

Hidden Hills, (unknown town, New Jersey); from The Neighbors (Just one gated community, where most of the residents are quirky for a very specific reason: they're aliens.)

LazyTown, (Iceland, maybe?); from LazyTown (this one I'm a bit iffy on)

Milford, Vermont; from Three Moons Over Milford

The Pit, Toronto, Ontario; from Liberty Street (Just one apartment building, actually called the Epitome.)

Ponyville, Equestria; from My Little Pony: Friendship Is Magic

Rome, Wisconsin; from Picket Fences

South Park, Colorado; from South Park

Springfield, (unknown state); from The Simpsons

Stars Hollow, Connecticut; from Gilmore Girls (One of my all-time favorite quirky towns.)

Twin Peaks, Washington; from "Twin Peaks" (I've never seen this show, but always wanted to)

(unknown town), Vermont; from Newhart

WNYX, New York City, New York; from NewsRadio (Just one radio station, but I consider its employees kinda quirky.)