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The chip is an MD-31 mold which antique gambling chips dates around the 1950s.
I did also read about the Hi Way Casino in Westport CT, and the timing does seem appropriate.
Keep in mind that the term “casino” in the 1800s and early 20th century was not used to describe a place of gambling, but any social gathering hall, with billiards, library, sports and meeting rooms.
It could be a chip used in a card game there, but wasn’t known as a “casino” as we use the term today.
It doesn't mean anything, really, it was just an artificial designation to try an organize chips by category, as cataloged by Robert Eisenstadt (RIP) for the Museum of Gaming History (MOGH).
You can find the website info by Googling "antique poker chips"