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2.
giving head along the Oregon Trail to your partner as they ford the river.
You can only ride in my wagon if you give me trail head the whole way to Oregon.
by WB's January 12, 2008
 
1.
The act of receiving or giving oral sex to someone while riding a horse.
"how'd last night go with Kyndra?"

"Dude we went went horseback riding...totally got some trailhead"
by Spice Trader January 30, 2012
 
3.
Giving head to your partner along the Oregon Trail/ any trail you please (ski slopes included).
You can ride in my wagon as long as you give me trail head all the way to Oregon.
by WB's January 12, 2008