Is September "off season" for ya'll? If so, seriously consider putting an effort into securing Tourist Development Council (or whatever it's called) grants. You are providing a surge of hotel rooms, restaurant patrons and the like....

Many cities/counties set aside funds for just this type of activity (to promote local business to outside visitors). Some are funded by bed tax, some have other means of funding...

Another option would be to pitch to the local chamber of commerce and rotary organizations, who may wish to participate in some way, either through discounts to racers or directly in terms of some logistics or organizational assistance. Heck, some may even want to sponsor something... They can then show their members how the "chamber works" for those member businesses.

It's probably a little late this year, but the cycle for 2014 event should probably start around Christmas (developing the "pitch", meeting with the groups) and serious pimpin online in July at the latest...?

This may or may not have to be a "by-sailors for sailors" event. It could be a community-wide rally combined with cultural or other sporting (kayak, fun-run, etc) events for the non-sailors/shore crew. Maybe reach out to the other local groups to see if they are scheduling anything the same weekend and cross-promote...