Normally motorcycle and car clubs do "Poker Runs" and go from tavern to tavern.
A poker walk is similar to a walk-a-thon - except you walk a designated route and stop at checkpoints to pick up poker chips (or playing cards). 5 checkpoints, if you're playing 5 card stud.
At the end of the route, the person with the best poker hand wins a prize (or cash). If you have a bad hand, you can buy additional cards for $1 each.
I've seen groups turn this into "sneaker" day - give prizes for the best decorated sneakers, etc.
Just wondering if the "Poker" theme would fly with the district.
With respect to the gambling aspect, 50/50 raffles are a form of gambling and as long as that is acceptable in your district, the poker function would probably be ok too.
To cover ourselves, just in case, we did get a permit for the raffles.