Organizing a benefit prize ride? Where to start?

Have any of you volunteered or organized a prize or poker ride? How feasible is it? Any tips you can share on what works and what doesn’t? Length (time and miles)? How many volunteers? Liability releases? Etc?

Kicking around the idea as a little fundraiser for a friend of mine with a horse rescue.

Your help is very much appreciated!!!

My local saddle club just wrapped up our 3d annual Poker Ride. I was the impetus for getting it off the ground, and helped get it all organized.

Insurance is the big “must” even with liability releases. Try as you might, you can’t keep everyone from being stupid. Our club has “horse club” insurance that also covers our specified public events.

Most rides I have been on range from 2 hours to 4 hours in length, with most clocking in around 3 hours. We run ours with about 8 people, but don’t do any concessions/food.

Feel free to pm me, and I can let you know more about what has worked for us and share forms, although they are specific to my state and its liability laws.