Please advise on how to organize an Alleycat style bike event fundraiser for my nonprofit workplace, and how to make it AMAZINGLY FUN.

I would advise, actually against it, as alley cats are really dangerous and if someone gets hurt, it's sort of a bummer. If you're doing it for an actual fundraiser, for an actually org, it's sort of goes against the anarchy that one can really be. Not to say you shouldn't do an event like this - I would really encourage a small, tight course, maybe even a loop with many checkpoints, with each checkpoint having some sort of other thing you have to do - for example, for 06/06/06, there was a race where you had to eat a deviled egg before the grand départ, a checkpoint would make you find a themed word in a word search, one made you play, like a 'round of twister, another had you get off your bike and do a small course on a tricycle. I would also suggest that you allow all the checkpoints to be done in whatever order you'd like, so no one checkpoint has too many people at it. http://www.youtube.com/watch?v=GMWSHuvT8V8 at the beginning is a lot of fun (this was a time trial type race). One alleycat I participated had a multiple choice quiz about the history of the city at each checkpoint. The only other part is to get a bunch of people that will work the checkpoint and have the start/finish be some place that's fun to hang out in, for a few hours. Maybe with beer. For the fundraising aspect, of course of a small, "donation" to be a part of the race and get local shops to throw in shwag for a raffle, or whatever. As well as the main event, consider a few games of foot down, or bike soccer, or bike polo or just sprints.

I would also advise against an alleycat race focusing on speed (speaking as a commuting cyclist, racer, and race-marshal/ride-marshal) as I consider alleycats to be dangerous and a selfish way of using a public space. However, I like your idea of people using different routes. Maybe you could get people to use gps tools (smart-phones, gps) and plot traces on a map in real time. People could get points on the most unused route between two points. Participants could get sponsorship from people in advance on a 'per mile' basis, and then based on the amount of distance they ride they would raise that amount of money.

One-off event-based fundraising in general is illadvisable because it requires a load of staff planning and a huge risk of failure due to weather or other unforseeable happenings. There's also a reason why alleycats and their ilk are thrown by loose-knit, informally organized cohorts. The liability is for being sued and, IANAL, but I'm pretty sure anybody can sue you for anything and you've gotta invest time in court and money in lawyers whether you win or lose. You're also limiting your fundraising demographic to a pretty small subset of pretty thrifty people who are into bike culture and further narrowing your target down to competitive people. I love me some bike fun, but I'd probably skip your event. WABA in DC has a bike prom. Free Geek in Portland has street fairs (not explicitly bike themed, but there's an overlap). The Community Cycling Center has theme rides, which sounds closest to your idea, but they're already a bike nonprofit and the rides are weatherproofed by theme ("worst day of the year ride"). A sustainable food nonprofit trying to shoehorn itself into a bike theme sounds not fun. A sustainable food nonprofit with yummy food booths, bike valets and music and an auction or raffle and maybe a bike blender smoothie maker sounds like fun. Bike-in movies are also super fun and low key from a planning prospective (and easy to replicate once you put the pieces together). Bonus points for powering the projector by bike (hint: this is super finicky and loud and you probably want to cheat and precharge a UPS and a laptop anyway, but it's a fun gimmick and it gives the competitive kiddos something to do.) Alternately, alternately, I attended part of a DC bike event in a bar that had stationary bike timetrial races with the Goldsprints software. Pretty boring to me, but the lycra, messenger and one-upmanship kiddos seemed to be having a blast.

I'd encourage you to reframe it away from "alleycat" - perhaps something like "urban brevet" or "fun ride" to downshift the competitive element. A ride (yes, perhaps too with prizes for first finishers) more so than a race. Alleycats are not inherently more dangerous than riding around a city, but you might have wider appeal not calling it an alleycat. Something more along the lines of a scavenger hunt? You can get sponsors and supporters most effectively if you know people at shops, local parts/gear suppliers and makers. Cold requests are a lot more hit-or-miss. You want to give participants good reason to participate. And you want to make it easy and fun for them, not hard - don't expect them to do too much work on your behalf. They're your customers. I'm not sure I'd want to pay to just ride around and *learn* about your org (though, as a new MPLS resident interested in bikes and food systems, I am quite curious) - you'll have to provide them with something. A party, food, booze, prizes - think it through. Collaborate with other organizations, artists, musicians - anything to both build buzz, appeal, draw and 'cross-polination' as well as to make each stop hilarious and awesome. Or just get the funnest people you know to treat every checkpoint like their own party, and give them the liberty to do what they will to participants. There should be a raging party at the end with a good reason (rad DJ? awesome band?) - and there you can find more ways to raise money. maybe a raffle? Sell food and beer? also, yes, Cranksgiving should help you think of ways to combine food and bikes. all that said, ditto to Skwirl's comment about one-off event fundraising. this might be difficult to do well if you don't exactly know what to do or how to do it.

Thanks for your thoughtful responses so far! I think the idea of shifting away from calling it and "alleycat" is a wise one--I know it started with bike messengers, but I didn't realize it had such strong connotations of danger and law-breaking (which reveals how naive I am!). This year, I participated in the http://www.babesinbikeland.com/ all female alleycat style bike race, and it wasn't competitive or intimidating in that way at all--it was more about people getting together to enjoy riding around the city. I definitely am going to talk to the organizers of that event for some advice. That information about League of American Bicyclists is great--thanks so much. Definitely a party at the end, and definitely some swag from local merchants to give away. I would like to work with a lot of local shops and producers as far as sponsorship goes, and my own plan is to enlist local bands for the final celebration. I would definitely love more ideas about what would make this sound fun. If you were a potential participant, what would make you want to come?

Check into the term 'Rally' as opposed to alleycat. You should also TOTALLY have a style component. I raced (ONE TIME ONLY oh god I was so slow) in one here, and while my team was very close to DFL, we were in the top 5 for style and that was AWESOME. (bike riding tutus FTW!)