The artist incorporated many Sioux symbols on this pony. "Woodland Hunter came to me through research and study of the northern plains tribes," says Kevin Kilhoffer, the artist who is a native of western Oklahoma. "I found records of a Franciscan missionary stationed at a fur trade fort dating back to 1836, and in his notes he described a Teton Sioux warrior who rode into the fort wearing a magnificent war shirt adorned with scalps and wonderful art work decorating his horse."

Using this description as inspiration the artist uses symbols for deeds, wisdom, wealth and bravery. He outfitted his Pony with a shield, weapons, saddle and bags for transporting food. Woodland Hunter is a historically accurate tribute to that plains Indian warrior.

Woodland Hunter pony was introduced  Winter 2006 by Trail of Painted Ponies. It was retired January 2009. The last Woodland Hunter manufactured was #5E/244. That means 50,244 Woodland Hunter ponies were made - making it one of the more popular ponies.