This is something that I may be working on as well myself next year. I would say see if you can work something out with your local cycling club. Work with their resources (ie insurance etc) and see if there is anyone who could help mentor you in the best ways to set up a local ride.
I'm lucky enough to have at least one ride leader that has offered to help me possibly setting up rides for people who ride more my speed and riding level [of course that's getting better all the time, but I don't want to forget where I started] He's offered to help me set up/find routes possibly on my side of town, print maps and cue sheets etc. I'm seriously considering it. The good thing about working with the local club is the fact they have more resources than an individual would. ron has offered to help me with a ride or two as well.
If you don't have that access, my recommendation would be to check out some routes [possibly some that you have ridden often]. Check for traffic hazards, road conditions, is it a route that would be easy for all levels of riders [rate of grade, etc] One fun thing is to possibly set up a ride with a destination to ride to [and or back] One of my favorite rides is the Carbos and Caffiene Saturday Breakfast ride. I can't keep up with all of the roadies, but periodically I have someone I can keep up with or will stay back with me. I know the route now and if necessary I can cut short so I can still meet with the rest of the group for breakfast at a pre determined meeting spot. The ride leader calls ahead to let them know approximately what time to expect and how many to expect. Then after breakfast, the real "meat" of the ride distance happens. Have alternate routes available in case you need to change as conditions or circumstances do. Do try to keep a main specified "RIDE" consistant if you can though. That's what will often keep bringing people back. If they ride once and find they're able to keep up and enjoy it, they'll return. If they never really know where they're going to ride or how they'll do, they might not.
It's going to be a big undertaking, so it's something I'm going to way over before jumping in. At least being able to work with the group, I'll have a place to publicize my ride a bit easier as well.
Good luck,
I hope I've been SOME help.
Mary



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