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Trail of Tears 

A happy trail leading to a disappointingly small penis.
“I thought I was in for a good time, but all Chad had to offer was another Trail of Tears.”

trail mix dick 

When a dick only has 1 good feature (like the m&m in trail mix)
Girl 1: How was last night?
Girl 2: My man had a trail mix dick, solid girth but no length
trail mix dick by Grizzly_Man January 4, 2016

trail tootsie 

A Trail Tootsie is a Hot Chick That can be found on wilderness trails. She is usually all dolled up with her hair and makeup done. They are always dressed to Impress, With big sunglasses, low cut tops, and Yoga pants. This is all done to take numerous selfies and attract other people.
Hey man! Look at that Trail Tootsie taking a selfie next to that tree. She looks hot in those Yoga pants.
trail tootsie by Air_Wolf February 7, 2018

Trail Thot 

Thots who are clearly not prepared to be hiking.
Clarissa took a yeti as a water bottle on a hike. She also wore flip flops and lost one in the mud, Clarissa is a trail thot.
Trail Thot by KenyanButtStuff June 16, 2018

Trail Mix 

M and M's with obstacles
Hay do you want some M and M's with obstacles??? or trail mix
Trail Mix by Jaxon's PP November 8, 2019

trail burglar 

A non-participant who enters a race course, despite a race in progress.
Bob is such a trail burglar. He decided to session the new jump line right in the middle of the beginner's race.