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The Trail was probably named for the Chisholm Trail which ran through Duncan. The Chisholm Trail was used to move cattle from Texas to the rail head in Kansas in the 1800s and many local businesses had “Trail” in their name — Such as the Chisholm Trail Hotel.
The Trail Theater was small and showed mainly cowboy movies. I believe it was closed by 1950 and the building was reused for another business.
See 1942 interior/exterior images by typing in word “trail”,