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A charity that I volunteer for were talking about running a cycle event, format still to be determined, as are a lot of things.
If you have run an event and useful information greatly appreciated.
And if you take part in events, what works? And what doesn't?
Local primary school did a road event that raised (for them) a huge amount of cash, did it via British Cycling, so advertised / entries & I assume liability insurance via their website. They also provided event flags etc.
I on the other hand put a thread up on here, made a cardboard box for donations & created a shonky route for people to follow. Worked well.
If you can narrow down "event" it'd help with replies: road, MTB, gravel, 24hr, race, sportive, sanctioned, public / private grounds, numbers etc.
It may be worth noting that all the cash appears to be in long / big 24hr solo / team running events, more so than cycling.
Biggest ball ache I've found is if you want it timed, and how accurate your system is. Either DIY via a spread sheet or get a timing specialist in.
Oh, and parking.
I've done it before - a mountain bike race in a Forestry Commission forest. They needed a license for us to use the forest, and we could use the forest free provided we didn't formally close any of the trails.
We didn't use a formal timing system, just took down numbers and the time they went through the start/finish area. This was OK in that it kept the cost down to £10 per rider but it was by no means perfect- there were, of the 100 or so riders, about 10 that we got their results wrong for. If you were doing a big long course event, say a 25 mile route where everyone goes off at the same time, you don't need a timing system, just a stopwatch and someone taking down the times the riders get to the finish line.
We used The League International for insurance- they were much, much cheaper than British Cycling and did effectively the same job. It was a few quid per rider.
Our biggest cost was portaloos (if you do go with a Forestry Commission venue, bear in mind that they don't assume events like this will require portaloos so you need a seperate license for them).
I did 5 or 6 Hit The Norths with Jason/Terrahawk, and he has since done more.
Things that you will need to consider:
•	Your budget. Cost it and establish your cut off date when you have to commit or cancel.
•	A course that will work. It has to be wide enough, long enough and safe enough. With good access and a big space for the start & finish area.
•	Advertising.
•	Entry payment method.
•	Insurance.
•	First aid provision.
•	Risk assessments.
•	Land use permissions.
•	Footpath closures.
•	Notifying the police. If mountain rescue get called out (and they will for even the most innocuous of reasons that you wouldn’t consider on a ride with your mates) the police will get notified. If they show up and find 400 of you in a field they get grumpy, even if you have submitted the paperwork but the local station haven’t passed it on to local HQ.
•	Parking, including parking marshalls.
•	Toilets.
•	Timing / Results.
•	Catering.
•	Litter bins and disposal.
•	Prizes.
•	Sponsors.
•	A PA system.
•	Sign-in/race control gazebo.
•	Tape, posts and cones. You will also need a printer, laminator and reliable staple gun (trust me).
•	Time and kit to mark the course and take it all down again afterwards.
•	Help on the day to run the whole show.
•	Loads of high viz vests.
•	Course marshalls.
•	…and the time it will take you do the above. Which is the reason why I don’t do it anymore.
Hugely rewarding, but hard work and stressful.
When I was doing this I would quite often read about proposed new events and you could tell that they had absolutely no chance of pulling it off. A nice poster and that would be about it.
Get a small team of 100 % reliable mates to help on the day. People that you can guarantee will turn up and put a shift in.
Give yourself plenty of time and cost it properly. Go to other events and see what works and what doesn’t.
At the moment it's still a little early but the site we have in mind would be suited to several different disciplines, although not road.
An annual sportive event is already run on part of the site.
Don't need to worry about mountain rescue as there's no mountains and the event would be raising funds for three different search and rescue assets.
Mountain rescue don't just do mountains. They do anywhere where you can't get an ambulance. From memory one of them that I spoke to said that the extract a lot of golfers who have taken ill on the back 9.
You'll still need to inform the police though. Nothing too taxing, just a form so that they have note of it. Our issue was that it didn't make its way to the right person at HQ (not my fault) so when mountain rescue showed up to extract somebody who has slipped in the mud about 100m from their tent a copper also showed up and I had a got a bit of a bollocking. The only upside was that it wasn't raining inside his police car.
Also, if you local authority is anything like mine (Bury) they will do their absolute best to extract as many fees out of you as possible.
We also had some gung-ho medic who wanted to bring in the air ambulance to help remove a bloke with a broken collar bone, who managed to walk the 200m back to race control whilst Mrs Rusty Spanners pushed his bike. This prick referred to the helicopter as “The Helix” and their quad bike as “Quebec One”.
Anywhere for Swimming an option at/near your chosen location?
If so consider running a Sprint Tri? 
Obviously depends on venue and facilities but it might have a slightly broader appeal than 'just' a cycling event?
Make the cycling leg offroad ideally on a grassy surface (should anyone tumble) running leg on grass too would also go easier on occasional runners knees...
All the same considerations will apply...
Thanks for the ideas to bounce around
British Cycling site has loads of info on there about running an event, things to think about. The first thing most prospective organisers go for is "insurance" without any idea of what actual insurance they need so there's a degree of assumption and misunderstanding around that for starters.
It's always the little things that people overlook. Zip ties, safety pins, course marking tape, bin bags, duct tape - the 1001 sundries of random crap that no-one realises goes into a successful event!
Toilets, parking and catering. And then cost all that up, work out how many people you're aiming for and therefore how much you need to charge per person to break even.
In terms of timing I've used Webscorer in the past - runs off an ipad or android tablet / phone etc. Works pretty well and depending on price can do some pretty complicated scenarios.
Timing, the simple answer is have two systems and double up if you can means four people but no results disaster which people can get tetchy about. It's a good activity for the switched on but less mobile.
Medical, depends on what you are doing, BC have tightened up but if it's a sportive type ride then you aren't going to need an ambulance.
Good luck