It looks like IFC Insane Rodeo by Anton Krylov (2010, Free for personal use)

This is a slab serif with median spurs. You may have an exact match in Anton Krylov's Insane Rodeo http://www.dafont.com/ifc-insane-rodeo.font?fpp=100&text=OREGON+TRAIL
Also lots of similar fonts, including several well made ones from Font Mesa:
Cowboy Western:
http://www.myfonts.com/fonts/fontmesa/cowboy-western/
Gold Spur
http://www.myfonts.com/fonts/fontmesa/gold-spur/
Don