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Trail Whore 

A female that is found in the hillbilly parts of the country, usually on the side of an unpaved road or trail that you can pay, bribe etc. for sexual favors.
While in West Virginia on our 4-wheelers we found some trail whores that we were able to rattle in for a good time.

Trail of Tears 

The small strip of hair leading down a girls back to her ass crack. Not a desirable trait in females. Typically found on Italian and Mediterranean women.
Oh shit man, it was all over when I saw her Trail of Tears. She has more hair on her crack than me.
Trail of Tears by daveOMG!!1! December 18, 2005

Trail Rated 

1. Jeep 4x4s are tested on the toughest trails in the world to prove one thing: THEY CAN TAKE WHATEVER YOU DISH OUT. The Trail Rated badge means that your Jeep 4x4 has been designed to perform in five categories of off-road conditions: traction, ground clearance, maneuverability, articulation, and water fording.

2.
a way to describe you that your ass is on the highest level of badness. or to describe a person or thing at the strongest level.
1.
nick: i heard you bought yourself a new auto.
jim: yeah, it's a ford escape hybrid suv with four wheel drive.
nick: too bad it isn't TRAIL RATED like my Jeep.
jim: (starts to cry)

2.
sally: what are you doing?
tina: i'm stealing your dog.
sally: you can't do that.
tina: bitch, i'm TRAIL RATED. i do what i want.
Trail Rated by millertim May 6, 2007

trail grommet

a lesbian aka jon mozer
trail grommet by Anonymous May 30, 2003

Trail to the rail 

commonly used by by skaters. means the distancce between the tarmac and the ledge or rail there grinding on
Guy 1: im gunna do this rail

Guy 2: no you wont, pop from from the trail to the rail too far

trail vision 

Trail vision is a relative explanation for a person in the Boy Scouts of America who has been on a trek,in camp,or simply has been surrounded by guys too long. Simply stated if one is experiencing Trail Vision they see girls only in 6-10 "rating" and nothing less.
"Dude do I have Trail Vision or is she a flat out TEN?!"

"Chill bud you have it for sure"
trail vision by Boe Jangles August 19, 2016