Quassy and Toughman you mentioned are great, though TBD how quassy will be next year with WTC - admittedly it is still in a pretty nice area so I have to imagine it would still be fun if you haven't done it already.

Obviously there is the NYC Tri, which I actually think is a ton of fun despite being extremely crowded. (Maybe I just like it since I live 5mins from the start)

If you want to go a little further to lake george, there is a half and oly there over labor day weekend. http://www.adkracemgmt.com/ I did it last year- it was shortened due to rain/cold but I'm sure it would have been one of my favorite courses had it not been for the terrible conditions.

I've also had the Salomon NY Trail series on my calendar, but I have never done it - definitely curious if anyone has any experience with it. Looks pretty cool. http://salomonnytrailseries.com/

There is also a North Face trail run at Bear mountain (I also haven't done it, but looks decent) https://www.thenorthface.com/...rance-challenge.html

If you want something to do this weekend: http://eventpowerli.com/mightyman-montauk/

Yes, SOS and AmZof (3rd week in May) deserve all the accolades. Simply no better multisport events. Anywhere.

Trail run, the epic (by all accounts): http://escarpmenttrail.com/bs/

Regrettably, it's the one close race I've never done (and is waaaay beyond my ability/fitness now).

Finally, you didn't ask about bike races but Battenkill (3 hours form NYC) is awesome.
http://tourofthebattenkill.com/

For the escarpment trail run, are there trail markers to show you which way to go? Their website doesn't show much information about the race

HITS Hudson Valley has all the distances and is 90 min away
Pass it Along Triathlon in Sparta NJ is a small and local race - about 45 min away
Event Power has an entire series on Long Island - the Mighty Hamptons is a great race

Race Awesome has a buch of races on LI, as does eventpowerLI. most should be somewhat accessible by train or car, and heading out to montauk for one of the many races that are held out there is usually a solid bet, if a bit expensive. in NJ, there are lots of cool little local races. Wyckoff Triathlon and the Jerseyman tri are pretty fun, and there are plenty of others. I'm only speaking from experience.

SOS is the coolest race, and Williams lake 70.3 is apparently pretty cool as well. There are also some really good swim races put on in the hudson up north if you're into that.

KIC IT triathlon in Stamford CT has a sprint and olympic. http://www.kicittriathlon.com. not updated but course is there and expect it to be June 23.

westchester tri is this weekend in Rye NY.

toughman tri (i think was already mentioned).

IMAC70.3 is close to 2 hours from NYC.

Thanks. Really great info from everybody. Much appreciated.

recommend connecting with Tailwind Endurance on the Upper West Side. Great community!

THIS.

AmZof is indeed back and better than ever!!!

https://runsignup.com/Race/NY/StoneRidge/AmericanZofingenDuathlon


AmZof has the highest fun & suffering / $ ratio in all of multisport!!!
And they're working on a new brewery sponsor too - which will be awesome.


SOS is a truly unique triathlon, but it sells out in < 5 minutes on Halloween nite at midnight.


There's the new baby brother SOS Cape Cod event, but that also is now SOLD OUT.
http://sos-capecod.com/


(I'll be doing the Cape Cod race, since I had technical issues and was not able to register for the local SOS)


Escarpment Trail Run is really, really great.
Also - REALLY, REALLY HARD.
Time-wise, its longer than a marathon.
After getting my ass kicked by it for a few years, I decided to do a much easier race the following July:
IMLP. ;-)

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float , hammer , and jog