I don't believe there's anything earlier than the ones you mentioned. This is likely water temp limited.
Neither is difficult (although Milton's bike is hillier) and you could just take it easy for the day and learn the ropes as opposed to winning the thing and just consider it a training day.

I did a sprint triathlon (went all out too) a week before muskoka 70.3 and was fine because I took it easy for the few days before the 70.3. You should be fine. And no, Milton is usually the first race of the season. Sometimes multisport has a triathlon race a week before milton, but you have to check. Sometimes Milton is coooollldddd....that is the reality of Ontario - a very short tri season :(((

Ottawa has a late May one.
http://somersault.ca/eventearlybird.htm

Though not triathlons, there are a few duathlons that could make for a solid rust buster.

If the Windsor area is not too far outside your comfort zone, the Iron Hawk Duathlon in Harrow on May 9 is an excellent event hosted by Lionel Sanders' old high school. If not, there is a small duathlon in Tillsonburg that is usually held in September but is contemplating a switch to Victoria Day that may be an option if the change is made.

That being said, as an above poster mentioned, Woodstock is not an overly difficult course and is an awesome location. With the later date, the water may even be warmer than past years! I doubt you will have much trouble bouncing back for the half the next week, especially if you just use it as a rust-buster.

Water temperatures are the limiter for early Ontario races. Woodstock has historically been two weeks earlier, but moved back in the year for a better chance of a warmer swim. Other than those races, you are looking at either Quebec, the Buffalo area or the Detroit area for your races.

Hope that helps a bit!

I agree with others here. A sprint tri 7 days before your half isn't a bad idea. You may even benefit. You could take the run a bit less than all-out.

Note that Woodstock is 750m/20km/5km while Milton is 750m/30km/7km.

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Quebec May triathlon have taken a hit... the earliest two of the seasons (Oka and Sorel) are now duathlons only - Oka water temperature was too low this year (and triathlon got cancelled) and in 2013, weather was awful, they let the triathlon happen and got lots of flak for it...

Earliest triathlon in Quebec is Joliette on May 31st 2015 (about 45min north of Montreal).

Thanks for all the replies. I actually live in Milton and did the race this year but may look at Woodstock for 2015.

I already have a full running season planned which will get rid of some of the early cobwebs.

If any early races appear, let me know.