Looks like you have a small fleet on your hands. But again, the OT serial number doesn’t seem to fit your canoe.
The Old Town canoe with serial number 05592 is shown as 16 feet long, CS (common sense) grade, CR (Charles River) model with spruce gunwales and rail, ash decks, seats, and thwarts, and fitted with a keel. The canoe was built in 1907, being finsihed on March 21, 1907/. The original exterior paint color was dark green. It was shipped to Hartford, CT on August 26, 1907. A scan of this build record can be found by following the link behind the thumbnail image attached below.
This scan and several hundred thousand others were created with substantial grants from the Wooden Canoe Heritage Association (WCHA) and others. A description of the project to preserve these records is available at
http://www.wcha.org/ot_records/ if you want more details. I hope that you will join or renew your membership to the WCHA so that services like this can continue. See
http://www.wcha.org/about-the-wcha/ to learn more about the WCHA and
http://store.wcha.org/WCHA-New-Membership.html to join.
It is also possible that you could have another number or manufacturer if this description doesn't match your canoe. The indicated length is different than the length you provide. As built, 05592 was not fitted out as a sailing canoe, but sailing gear was often not provided at the factory, but by the dealer or other aftermarket supplier.
If that is the case, photographs of the deck, side profile, seats, and other details would be helpful in identifying the canoe. Does the canoe have the typical OT diamond head bolts?
Feel free to reply here if you have any other questions. Feel free to reply here if you have any other questions.
Greg