CatWoman,
2 solutions to that problem:
1) Have a regatta. Invite a whole bunch of people to come play in your backyard. (Easier said than done, though.)
2) Travel to a regatta. Get the thing on a trailer and hit the road. There's a CRAM regatta in Benton Harbor, MI (see either of the links above). There's also
CRAW. They have a whole bunch of stuff in Wisconsin.
Wanna see a "real" regatta? Come to CatFight in Muskegon August 19-21. There'll be close to 100 boats there. (Trusty computer says it's only 214 miles.) Leave in the middle of the day on Thursday and you won't have to deal with Chicago traffic.

You can take either of your boats to any of these events.