I’ve done this. Races are lots of fun, and contracts were what I used. It started in highsec, and had a shortcut option to go through low, and finished in highsec. All the racers decided to use the lowsec route.
We had security (to prevent ganks) at the start and finish; but that was my choice. One of the participants brought fireworks, to celebrate afterward. It was a great idea. Fireworks just seemed to finish the event off in style.
I offered prizes, for the top three finishers.
I didn’t charge entry fees, as it was an event put together by me, for my corp (at the time).
I did choose to send out a series of promotional “emails” to hype the event, and tried to make the emails humorous and engaging.
I had the entrants contract the pickup items back to me at the finish station, just so there was an official record as to who actually finished first. This was fortuitous in my race because the winner and second place were separated by literally seconds.
The whole event ran about an hour; but, the party afterwards extended that somewhat.
We did use comms, and had our version of “color commentary” as the race unfolded.
I also did an after-event writeup, at the urging of my CEO.
I don’t know if you intend to have the start and finish be at the same station. I didn’t do that. So, to facilitate “hosting the event” I had a jump clone at the finish station, so I could be there to hand out the prizes.
Organizing something like this for the first time is a lot of work. I’ve helped organize other events, and I suggest you have at least one or two others to help organize and promote your race. Done right, I think you could actually make money at something like this, if you were willing to put in the effort.
The most nerve wracking thing for me was not knowing exactly how many people would actually participate. Pilots will want to participate; but, “real life” comes first and that will heavily impact the participation, or lack thereof.
Be flexible in hosting, and try to instill that in the participants, too. My first event, had a series of unexpected/unanticipated side actions; the most notable of which was an Amarr faction war miltiaman trying to shakedown our event securityman for ransom isk…as the racers were…racing; and, it culminated in scaring the the residents of the finish system into leaving the system. One of the final race participants overheard them (the “residents”) in “local” in an adjoining system trying to figure out just exactly what all these “weird” pilots were suddenly doing in “their” system.
It had never occurred to me to advertise the race in either the starting system or the finish system. The starting system was a busy, well populated system, so having a bunch a guys from a single corp show up presented no problems whatsoever. The finish system was isolated, with a very low resident population; and apparently the vacated residents felt we (as in my corp) might be on a “ganking spree” and up and left when we started showing up in numbers in “their system”. It was a prudent move; but the “overheard” convo in “local” provided lots of hilarity for the racers and partiers and, of course, I as hostess tried to capitalize on this and milk it for all the humor I could. That’s what I mean by flexible. Seize your opportunities and make hay while the sun shines.
I think all the little incidents, like the miltiaman asking for ransom, added to the race. It gave it color, life, and gave everyone, who was there, funny stories to tell afterwards.