Through the help here I was able to find this page with some very interesting history regarding the paddle: 1947 Canoe Trip.
Especially interesting is the passage explaining the red tip on the paddle:
"That evening, after supper, a solemn ceremony was conducted by the Commodore and old timers. Based on the lore of the French fur traders of old, pine springs had been gathered in Naples. These were no shown to us "first-timers" as a marker of the furthest point in our journey. The red tips of the paddles were explained as representing the blood of wild creatures and fierce marauders who had attacked those traders, known to history as courageous and colorful "Voyageurs". They had, after all paddled deep into the North American continent and eventually followed down the mighty rivers to New Orleans."
If anyone comes across further information, or could help to narrow down a date for the paddle, I'd love to hear what you know.
Thanks!