Nice finds! The two tokens have been attributed to Deward, MI. Neither Cunningham's MI Token Book or TokenCatalog.com have anything to say about the history of the piece, unfortunately. A little Googling shows that it had something to do with the construction of the Detroit & Charlevoix Railroad.
John in the Great 208
Deward!! Deward, Crawford County; named by his heirs for D(avid) Ward whose estate was a vast pine tract; he died in 1900 and they liquidated the estate by exhausting the wood; the town started with their mill in 1901 and ended with it in 1912.
Don.....