Besides not overestimating how things will turn out, just go and ride as you planned to ride. Who cares who else is or isn’t there. My 2 cents. Dance like there’s no one watching.
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Unless they’re Cat 3/4 racers and you’re a recently retired WorldTour pro (in which case racing hard would definitely be kind of jerky!) a 3-6mph speed differential doesn’t sound like they’re turning up to race with an expectation of winning, they’re turning up to take part in a charity event. I wouldn’t worry about it, just ride at the pace you want to ride at and get a good workout, and if you do win by multiple minutes I can’t imagine in a local charity event anybody is going to be anything but happy for you. Can always donate any prizes back to the charity or put them into a raffle or something.
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Charity rides aren’t races. But you should go and crush them anyways. Just don’t brag about it afterwards. Lol
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Just name the event here and let all of your local TR folks come out to race you
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I am confused. Why would it be bad for you to win this race (as opposed to someone else)?
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In my experience, triathletes sign up early for events, and cyclists are far more likely to sign up the week of. If I were you I would just plan to ride it and I’d guess there are going to be some stronger riders who sign up in the next three weeks.
If not, set a time goal and go try to beat it.
I would bet this will take care of itself as I said above. To show up to an actual race and give less than your best is lame IMO. To PLAN to do that is to set yourself up for a less fun time and probably get beaten by someone you could’ve competed with, IMO.
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Yeah I know I’m saying it as a bit of tongue and cheek, but you should support the ride by riding, not skipping and using your entry fee as a donation. They want you out there
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Most races here in SoCal if you look at the entry list three weeks out, it’ll have like two guys in every category except 4 and 5. Then you look when online registration closes and the higher categories are up to normal 30-50+. Lots of people have stuff going on where maybe they aren’t sure if they’re going to do something, and a 66-mile charity race probably isn’t an A event for high level riders. It’ll just be a “oh, this thing is going on this weekend… I’ma go!” Lots of people do this.
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I’ll be interested in hearing back from you after the ride and see if you actually “win”. Now the pressure is on. 
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Do you know EVERY person registered? I’d just show up and race and you’ll figure out quickly if somebody keeps up with you. Or if you definitely don’t want it to be a time trial just hang back and chill with others.
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lol it seems you do have too much free time.
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Your overthinking it just ride, enjoy and see how it develops on the day 
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Assess all the other riders for a little while, if you think you can smoke them, just hang out, take your turns, enjoy the ride, then give it just enough welly to make it seem like a race finish 
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Really?
You are worried about winning a charity event and post this ^
Not sure what is more “Jerky”, my honest opinion (I can’t believe others arent thinking this as well.)
Just for information I wouldn’t read anything in to ‘Strava Stalking’ I know someone at our club that did that and was over confident… they didnt win, it wasnt even close.
Anyway, if you can win it do so and donate the prizes back, that would be more classy IMO.
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Honestly you havent.
Just go ride enjoy it.
If you feel uneasy about taking an easy prize, if you take it, just donate it back.
To be honest, you’re already not doing that. Treating them like your 6 year old daughter by letting them win or whatever also isn’t being respectful of them. Being respectful of them is bringing your best effort, and if they can’t beat it, then so be it. Assuming you’re that much faster that you’re just going to soft pedal around and half-ass it is disrespectful to start with. Show them respect by racing to the best of your ability.
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You’re not disrespecting them to their faces, but going into it assuming you are far and away the fastest best whatever to the point that you are wondering if you should “let” someone else win is not how I would define being respectful of my competition.
Being respectful of competition is assuming you’re going to need a strong effort to compete and have a shot at winning. You owe it to your competitors to give them your best effort.
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What I was saying in more diplomatic words.
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