Timberman is an awesome race and venue. Did it last year. Going back this year. I think for your purposes it's better than Maine. Maine bike course looks extremely flat on paper. Timberman had some rolling hills to it. I don't know what the Poconos course is like. I did it when it was an IM race in 2012 and am not sure if they changed it or not.

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Timberman is a terrific race. Well supported, well run, nice course. Don't know about the Poconos, but I've done Timberman twice, and both times I've been racked next to people who have done the race multiple times because they enjoy it so much.

Out of the three you mention, I've only done Maine.
I'll just say that, if you happen to have a young family traveling with you, the Maine race is a great choice. You are right on a really nice beach, and there is a fair at the end of the beach.....kids loved it.

Had a feeling that Maine would be a good family venue. Kids are 3yrs and 16mo so racecation there is a possibility. Timberman and Poconos looked more interesting from a racing standpoint but tougher logistically if the family comes along.

I'd vote for Maine, having done Olympic distance at both Maine and Pocono. With a family, the beach setup in Maine is MUCH nicer. The roads are better too; the finish stretch on the Pocono course last year had some awful pavement in it - even though it was closed to traffic for that portion. The Pocono swim was fine once in the water, but the start area is a little creepy and the banks of the lake are unmaintained - tougher on spectators/spouses/kids. The Maine saltwater swim is COLD but the salt adds a nice lift to the wetsuit.

Probably better training race for Lou. Would you say it's family/spectator friendly or better to drop in solo for a couple days ?

There isn't an ocean beach and a park at Timberman so Maine probably wins there, but the area is beautiful. There is probably more to do in the winter with Gunstock being right there. Though the hiking would probably be great (not that you'll want to) and there are zip lines at the mountain. I love the area because it's quiet and peaceful and the lakes are beautiful and clear. Drive up to Meredith for dinner and relax a bit. No kids for me so I'm not great at looking at it from that perspective.

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I'm also doing imlv build and had to choose between poconos and timberman. I did timberman last year and thought it was great (my second favorite of 5 halfs so far) and believe it would be very good prep course for imlv. Only reason I'm doing poconos this year instead is because it's 3.5 hrs closer to home.

any clue how many slots still available at timberman?

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2024: Bevoman, Galveston, Alcatraz, Marble Falls, Santa Cruz

Not sure. Decided to go a different direction and signed up for Muncie in July and going to head out to Colorado end of August for some good riding at altitude.

Haven't done Poconos, but here is how I would compare ME vs NH:

Event: Timberman is bigger as an Ironman branded race. The transition / post race area is nicer. Post race food was better. One free beer at Timberman / none in OOB. Advantage Timberman

Location: both are honky tonk areas. it really comes down to whether you prefer Ocean vs lake/mountain. Portland, ME is a great little city for visitors. OOB is pretty trashy, but again, so is Laconia. Advantage OOB

Swim course: neither is very warm. I prefer running into the ocean and doing the swim there--it feels a little more hard core, which is sort of the point. Slim advantage: OOB

Bike course: Timberman is an out and back, OOB is a loop. Timberman has a couple more challenging sections, but neither is a killer. Maine might be a little more scenic. Slim advantage OOB

Run course: Timberman is on a crowded double point and back course. this was my least favoriite part of the race. It felt like the priority for organizers was to find a nondescript 3.3 mile course to minimize road closures, police details, etc. OOB has a single point and back, a good portion of which is on a scenic rail trail. Advantage OOB

Bottom line: OOB has a better course, IMO, but TImberman is more of a happening.

As for taking young kids, mine love the Palace Playland and OOB. if there, get the Pier Fries -- horrible training food, but a necessary indulgence.

FWIW, I am doing both races again this year.