I'm in "either way"

We did the ride! 
Plan was to take the 7:14 from Jamaica out to Montauk in order to have a tailwind for the ride. I barely made it on time riding through some gnarly rain, but Max's train coming in from Penn did not due to some signage issues. There we had our first hour of delay - but also a chance to get some coffee. We met two other riders at the station that were going to do the same ride, also opting to ride back along the northern part of Long Island.
We made it to Montauk by 11:15, and were ready to ride back to the city. It was about 70F, dry, with light clouds. Perfect for riding. The weather projections were not looking great, but we chose to just ignore that. The two other riders decided to make the trek to the lighthouse first, Max told me he'd been there before and that it wasn't much special. Seeing the super pro gear and aggressive positions on the bikes, we fully expected them to overtake us before we'd reach the city. 
First 50K were pure bliss. We had a 4Bft tailwind and blasted through East Hampton, Bridgehampton (there's no bridge there??) and Southampton averaging 36 km/h. We hadn't even once put a foot on the ground when, in a village called Flanders, we encountered a duck. Not just a duck, but a GIANT duck shaped building by the side of the road. Turns out, it's built in 1931, it was a duck farm shop, it's a monument, the eyes are made of Ford Model T taillights, they used the carcass of a cooked chicken to make sure the thing was 'anatomically accurate', and and..  Sorry for this tangent, when I got home and had dinner I went into a rabbit hole of buildings shaped like animals. There's also a KFC somewhere that looks like a chicken and has a moving beak. I kid you not.
I guess the Big Duck made us hungry, so at 140K to go, we stopped in Riverhead for lunch: rice and a crab burger. Great fuel.
It can't be a coincidence that it also started raining in Flanders. Silly me thought that by the time we'd be done eating, it would've stopped. Of course not. Despite the many times we said something like, 'oh look, the rain seems to be getting more moderate', we just had a continuous heavy drizzle type weather. 
A large part of the route that followed was along a trail that, as Andrew said, had a lot of stop signs. Still, it meant a respite from the many busy roads we were riding along for the rest of the route, so it was worth the stop-and-go at that point.
At the halfway point, everything I had on me was soaked. I wanted to text our whereabouts to Dave, but couldn't use my phone anymore because there was no way to dry off the screen - or my fingers. That made me miss having an old school Nokia for a moment, although I don't think they'd be waterproof enough. I managed to send a voice memo to Dave telling him that the weather was terrible and that he should just stay home, but to no avail. Somewhat later, Max had a flat. We fixed it under some tree coverage and continued on. As long as we were riding, it wasn't cold at all. Standing still however.. 
By the time we were near Huntington, I saw a cyclist flying riding towards us in a super bright orange jacket. For one moment, I wondered what other idiot would go for a ride in this type of weather. Of course, it was Dave. We greeted by calling each other maniacs, insane and crazy, then rode on, with Dave hammering in front. Seeing how drenched we already were, the crazy amounts of spray from his rear wheel didn't really matter much, and it was just glorious to have a fresh pair of legs to follow for that last part. We went over some climbs that I'm sure would've been fun if it wasn't for the 180K we already did, then entered the city along what was pretty much a highway. Said goodbye to Dave at Cunningham, and noodled through Queens from there.
When i started cleaning my bike the next day, I noticed that a huge amount of rain water had found its way into my tires. Oh, and the two pro-looking guys? They turned around at Riverhead: it was too cold and too rainy for them. For us? Well, I guess Dave, Max and I are well-prepared for any type of Flanders-style spring races that comes up between now and next summer.
Strava: https://www.strava.com/activities/12527534982/overview

Fair play lads !
it’s not often you read about a ride you bail on and then think you probably made the right call 😂

LennartZandbergen said:

 We hadn't even once put a foot on the ground when, in a village called Flanders, we encountered a duck. Not just a duck, but a GIANT duck shaped building by the side of the road. Turns out, it's built in 1931, it was a duck farm shop, it's a monument, the eyes are made of Ford Model T taillights, they used the carcass of a cooked chicken to make sure the thing was 'anatomically accurate', and and..  Sorry for this tangent, when I got home and had dinner I went into a rabbit hole of buildings shaped like animals. There's also a KFC somewhere that looks like a chicken and has a moving beak. I kid you not.

Sounds like an epic ride (even if that term is overused. My 24 year old son has driven his friends to see the Flanders duck. He loves the fact that there is an oversized duck in the middle of nowhere for no particular reason. 

That's so funny that you came across the big duck. I grew up in Nassau county and one summer my mom randomly decided the family was going to make a day trip out of going to see it. Very fond memories of the silliness of it. It was an on going joke in my family any time we were bored we'd go see THE BIG DUCK!

 Sounds like a great ride, I was a bit worried for your safety, Long Island never struck me as safe for cycling.