if you're around for the weekend, there's the Escape the Cape open water swim (1m & 3m) on June 9 and Escape the Cape Tri (Sprint/Oly) on June 10th. I got an email from them today so know it's not fully sold out. Cape May just a few miles south and far nicer area to run or ride than Wildwood (IMHO).

Obviously, there's the ocean for swim... not sure if there's anything group organized. For bike I'd suggest calling a local bike shop, or you might want to look up DelmoSports, that's the RD for Ironman 70.3 Atlantic City and the races I mentioned above, Their office is actually in Wildwood and I'm sure you could call or email them for suggestions... assume being local they would have info. I'm not a Strava user but sure you can find some good rides in Cape May area.

Good luck

Thanks for the info. We're leaving Sunday but I might be able to make the open water swim on Saturday.

Too bad you can't do Escape the Cape. I did it last year, a truly spectacular, top notch event.

I've been going to Wildwood for a number of years now, I dont do any "group" activities but lots of S/B/R training while my wife relaxes on the beach! for running, the beach is pretty great early in the morning before crowds roll in, and same for the boardwalk. i'm usually doing stuff in the morning to beat the heat anyways and having places which are normally crowded to yourself is a double bonus. swimming, I didn't bother even looking for pools, went for the ocean. as for riding, i've had success going the ocean drive route, up thru stone harbor, avalon, sea isle city, all the way to ocean city. in terms of the towns, wildwood itself is the worst to get through. the rest are much more quiet, quaint, and pretty. wind can be a factor, coming off the water. you can also head toward cape may. i personally love the ride south out of wildwood, down into cape may then out west on sunset blvd to the lighthouse, then up to the higbee beach area by all the vineyards out there. up around the airport there are some good roads too. Just stay off 47. wayyyy too many 18-wheelers and road debris (yes, I got a flat so i'm bitter at that road). besides places which rent beach cruisers (and know nothing of road bikes), there is a lack of bike shops down there, at least I haven't found any - so bring spare tubes or other things you may look to a shop for in a pinch.

if you enjoy nice delicious beer, make sure you go to cape may brewing co.

Look up the Wild Harbor Tri Club.
Organized activities in southern Cape May County.

Von Savage Pool in Wildwood Crest has a convenient schedule for laps

There are countless roads throughout the area for a good bike ride.
Totally flatland, except for bridges and overpasses, but the headwinds make up for it.

You might also look up the Cape May Running Company for a good number of organized runs.

If you are around Saturday for the swim, I highly recommend and Delmo sports event. This one is real cool because they take you out on the cape may ferry and you jump off to start the race. As far as training, keep it simple. Run on the boardwalk, but get out there early. Its packed with bikes and kids once you hit 9am. For local bike training, when I'm down the shore I do one of two options. Take ocean drive, it pretty much connects all the shore towns, you get to go over all the bridges that connect them. . Again, get out early, and there will be no traffic. The other option is Rt9. Its the back route between all the shore towns. Most of it is wide and has a generous shoulder. Most times I make it a loop, Rt9 in one direction and Ocean Drive in the other.