Thank you for sharing photos of your chips. I believe that those two chips were made by the Burt Co. (Portland, Maine.)

Both of them probably date to the 1950s, possibly late 1940s or early 1960s.

The Paulson chips are on what we call the Short Cane Version of the classic Top Hat and Cane mold, and were likely made sometime after 1975, perhaps much later. The time difference makes me think the two older chips may be unrelated to the club you found them in.

The chip on the left is on the Hourglass mold. http://www.antiquegamblingchips.com/molddesign_manmade.htm#md80

The chip on the right is on the Roman or Weave mold.
http://www.antiquegamblingchips.com/molddesign_other.htm#md89

As far as I can tell, the origin of those two chips are unknown. They were likely both made for illegal clubs.

The red Weave mold chip was most likely hot stamped by the Penn Specialty Co., in Allentown, Pennsylvania. The fact that you found it in the same state as where they were made makes me think that the club it belonged to may have been in Pennsylvania.