I did the Diamondman Sprint last year. Swim in Lum's pond was fine. Bike is flat, a couple of the roads are busy but there was a big shoulder and I think 1 lane was closed. Run is through the woods and predominately shaded and pretty flat. I enjoyed the race. It was a Piranha Sports race last year and is now a Kinetic Multisports race.

Waterman's is a swim in a protected marina, flat bike route, flat run route. Plenty of kids doing that sprint course every year.

Awesome that your son is doing a sprint! I ran my first half-marathon (Disney) when I was 13 coached by my dad. One of my best childhood memories.....

Another good beginner sprint event if you get to the New Jersey shore area is Brigantine, NJ......held every August. That was my first event....nice area.....very easy logistics....and very beginner friendly.

Waterman's would be a great first-time race. Protected swim. Flat bike on roads with minimal traffic. Run is also flat on a very simple course. Rock Hall is a nice small town which makes parking/etc easy. The Kinetic events are very well run.

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Another vote for Waterman. Much of the swim is shallow enough to stand. In fact my 11-year-old is doing the swim leg of a relay this year. The only big downside is lodging in that area is challenging to find.

Don't leave out Savageman 20 as a possibility (also by Kinetic). While the longer distances involve lots of climbing the 20 is pretty flat.

This may be too far south for you but Rev3 is putting on a sprint in Stafford, VA on September 16th. It's a pool swim and the bike course is just a bit rolling and the run pretty flat. There's also a kid's tri there that both my kids have done and it's much shorter but a good experience and some of those kids are disturbingly fast. He'd have to still be 14 on 12/31/18 for the kids' race.

Yep- we are doing Watermans this weekend.
He's nervous (so am I) but will do great !!!
Thanks all.