Thanks for the input guys! These are left overs from a friend of a friends estate. It was run by the family and everything was very very overpriced by some appraiser so there was lots of great stuff left after the sale. The canes were put to the side by one of the family members from the start.
So far looking around on the internet I have learned that it is a Dartmouth tradition to have a cane to walk with at graduation for different clubs and societies and such. They used to have a Native American mascot until the 1970s. The cane would then be passed around to friends/peers to be carved/signed much like a yearbook. In addition to the Indian head cane, I have walking stick with the same owners name, this however appears to be from their fraternity, signed with initials of fraternity brothers. According to my research he most likely took a beating with it then was given it as part of his initiation
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Here is a pic of the carvings, close up of the black canes handle.
