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1.
Skidway Lake is a town in Northern Michigan so nefarious that its' name has become a common slang term used to describe something cheap or dirty. It was once a popular vacation spot, but is now a heavily blighted town (burned-down houses, four junk cars and a toilet in the yard, etc. etc.) and a popular place for police to conduct drug raids. Some people refer to the town as "Little Flint" due to its' crime rate and abundance poor & trashy inhabitants. However, unlike Flint, Skidway Lake isn't racially diverse at all. It's a mostly white enclave of poor people who rent cheap cabins and trailers (of which most are in desperate need of repair) owned by the few local business people (slum lords) or folks from downstate who realized it wasn't such a great place to vacation anymore, so why not rent it out to some poor suckers who don't know any better. Others call it "Skidmark", "Skidrow", or "Skankway". Some residents avoid admitting they live there at all by referring to their mailing address, which uses the Prescott zip code, or Mills Township - which is the official designation used for any manner of legal purposes.
Guy 1: Can I borrow five bucks?
Guy 2: No, but we can go steal my grandma's bottles and return them for cash.
Guy 1: Damn, that's so Skidway.

Girl 1: Who's that guy?
Girl 2: I don't know, but he looks like he's from Skidway. Let's get out of here before he tries to get us pregnant and give us the herpes.

Person 1: What's Skidway?
Person 2: The way your mom dresses when she's out trolling for a new husband.
by TheeJenniBurger October 30, 2009
 
2.
Automobile losing traction While going sideways
We came into a hairpin corner, hooked second gear and threw the car skidways.
by Vinnie Hitchcock July 13, 2006