How to Make It to Montauk

My friend and I took http://nymag.com/guides/summer/17424/ a couple of years ago. It was a really nice ride, lots of pleasant scenery, plenty of room on the shoulder for most of it, not complicated at all. I highly recommend it.

that is OP's route but avoiding Nassau and Queens via the train.

Oops, why so it is. In my opinion, it's worth is to take the train and avoid the nasty business of getting out of the NYC metro area. Once in Babylon, you'll have plenty of nice long stretches of uninterrupted riding.

JPD, where are the Pine Barrens? Or rather, at what point would I cut down from 25a to 24? To get from Roslyn to 25, would I take 107 (N. Hempstead Turkpike) to 106 (Jericho Oyster Bay Rd) to bypass the Long Island Expressway?

I'd suggest doing Babylon to Montauk. Glen does that century ride earlier in the summer, so does 5BBC. The route I've taken each time is MUCH more through side streets and cute, low-traffic areas. I'll dig around and see if I still have a cue sheet and if so will mefi mail it to you. I took a look at the 5BBC link you sent and the route I'm suggesting is much tamer and safer. I know the route I've done with Glen/5BBC started in the parking lot of the Babylon LIRR. I'll see what I can find... have fun! (on link review, @ololith's link looks similar if not the same)

Otolith, it sounds like you still need to go though a lot of traffic and suburbia if you leave from Babylon. Did you find that to be the case?

25a not 25. The Pine Barrens are great big empty area out in Western Suffolk. N. Hempstead Turnpike is 25a not 107 There are 2 24's - Hempstead Turnpike (Don't want) and Riverhead Hampton-Bays Rd (maybe want)

Whoops, Google maps failed me. The go through the Pine Barrens, would I turn south towards 27 on County Rd. 105/Cross River Dr.?

In my recollection, we didn't have to deal with a lot of traffic on the ride. When going through the center of towns along the way, traffic was slow and not a problem and when on the faster roads between towns, I felt quite safe with the amount of room we had on the shoulder. I'm a nervous cyclist and getting around in NYC gives me stomach cramps, but I don't remember any times on the Montauk ride that it felt uncomfortable. It was rarely even necessary to take up a lane of traffic, since there was so much space on the side. In terms of suburban density, yes, there are a fair number of towns along the way. But it's not like you're riding through constant suburbs. There's plenty of green space on the route. I actually found it pretty interesting riding through all of the small LI towns.