I'm going to ride to the Montauk point lighthouse with my friend Max next week Saturday, 9/28, and we're looking for people to join us!

This is the route i've drawn out. I saw the route the Major Taylor team did earlier this summer. They opted to ride over Sunrise Hwy from around Rockville to Babylon, which looks pretty sketchy on streetview. I opted for a seemingly safer road, but I don't know the area so well so maybe someone that knows their way around there ( @PatrickGrehan ?) could offer advice for the route building.  

@LennartZandbergen

THere was also a formal Montauk ride this past Sunday.  

That would be awesome JP! Even better if you can find a way to fit it into your training plan after all ;-)

I couldn’t find a gpx of the full route from last weekend’s montauk ride yet, only a couple that only did the final 70 miles or so.

there are also some routes that go through the northern part of Long Island, but I’ll try that another time.

I've been wanting to do this ride as well, but sadly won't be in town that weekend.  

I think I might have egged Myles to create a quieter route from Manorville to Montauk.  here's his take:
I can't speak for the western end of stuff, because that's all heinous and horrible, and there are maybe sharks.   

But I'd definitely ask Pat (@patrickgrehan), as he lives in that hood and can likely advise on the western portion of this jaunt.  

(which is serious, a lot of those roads are heavily trafficked, no bike lanes, and it seems like it's sort of main roads which you can' ride on, but probably shouldn't.  

This is a direct route, see how straight the line is.  So if you CARE about keeping mileage down, it's fine. 
Come like.... Westhampton ish, you can do a lot better/more interesting/safer/deserted sort of mileage.   It might add.... 20 miles but you could ride the hills by my house, and other areas that are cool and not main roads where you might die. 

Thank Myles for this, very helpful! 

The good thing about the scary western part of it is, we'll be doing it in the early AM, which I guess/hope means less traffic. 

Did some digging on a northern route, looks like there are some extensive portions of dedicated cycling trails on top of old railroad lines on that side of Long Island. This seems like a safer/more fun route, with only 5 extra miles. I'll do more research tomorrow. https://www.strava.com/routes/3271319029277451602

I didn't see this thread yesterday. 

@LennartZandbergen The route you put on the south shore avoiding sunrise highway is an improvement. Sunrise highway is wide and has a shoulder, but it's not a road that I would ever want to ride a bike on. Taking Hendrickson to lakeview, to Seaman, to Smith, to park to Smith will be a smart choice. I am less familiar with the roads as you get further east on the South shore. To be honest, I usually avoid riding not he south shore because 1) very congested with car that dive too fast, 2) lots of strip malls and lack of shoulders that are very cyclist unfriendly, and 3) the culture out here isn't one that expects to see cyclists so they don't know what to do when they see one. Having said that, the roads you picked above are not major roadways and therefore should be relatively safe.

I have spent more time riding on the north shore. The properties are more expensive so they are more spread out and there are fewer strip malls. More oversized vehicles and often a lack of shoulder, but the roads are generally prettier and less travelled than on the south shore. You can take the LIE service road for a good portion of Nassau county (and into Suffolk) safely. There is a shoulder and cyclists often ride here. Note that there are traffic lights (which you have to stop at because it's safer given the congestion and vehicle speeds) and more rolling terrain, so even if you only add 5 miles to the route it will likely take you longer than on the south shore. There is an old real trail that they opened up on the north shore, but to be honest I haven't checked it out so don't have any good advice about it. 

Thanks so much Patrick! Currently inclined to check out the routes north, if it's nice there and the LIE service road isn't so bad it could be a nice change of scenery for a weekend ride, too. 

I might be able to join partway 

I grew up on the east end of Long Island and can try and offer advice, but it’s been a while. I might even try and join!

I would avoid most highways and even service roads. LI drivers are crazy and do not like cyclists. Once you get far enough east on some roads named “highway” they turn into just busy roads with lights and I would feel safe’early in the morning.

North shore routes are chill but it is gonna add a lot of time and miles to cross down to the south shore. Once you get to the Hamptons it gets pretty chill.

Check out the route they used for the recent Race to the End of the World https://strava.app.link/kUHTEZho0Mb

I’m probably going to do this with you guys 
Let’s figure a good meet spot

Mark Taylor said:

Also , its cool to actually ride the boardwalk all the way to the far rockaways and cut up through the 5 towns, Lawrence is the 1st , instead of doing al that nasty queens business '

BTW , the wind direction for this ride makes a huge difference to the amount of fun you'll have , although you are dutch , so you probably like a head wind.

I did this route , didn't go all the way to "the end "

https://ridewithgps.com/trips/51155611

This route looks a bit better, I'd still modify a few sections from roughly West Islip to past Bellport.

I also of the opinion to stay off Sunrise Highway as much as you can. That is a death trap and with Lawn GuyLanders driving like they stole it these days...

On almost the north shore there is a bike/ped path they put in from East Setauket to somewhere out in Shoreham. I have ridden most of that at some point and generally do not like it for a few reasons. You have to stop every time the path crosses a street, and other path users meander with no regard to other users. So I generally stay off unless it's at off hours or something.

After looking at Veloviewer's street view function for a while I'm still pretty inclined to take the north route over the southern one, as the roads just look more cycling-friendly. There are some more hills, but they are very short and also help to make things less boring! We'll see how it goes along that bike path, if the stopping at every street/meandering people annoy us, we can reroute to the more or less parallel Route 25A.

@Mark Taylor @DavidVibert , you could join from my place, I can have coffee ready! For @David Yang: I guess we'll come pretty much past your house? 

Yep I can't go all the way out with you but if you're on the north shore esp 25a that's actually going right by my house.

I was talking with Myles today.  He's going to put together an interesting route from around Manorville to Montauk.  Should do it tonight, probably on MapMyRide.

He strongly suggests downloading the LIRR app on your phones and making sure you know when the trails are leaving and where.  

Interestingly enough, roughly Brooklyn to my place in Smithtown is around 40 - 50 miles. Round trip would be in the range of 100. Amy once rode towards me from Brooklyn and I looked at her planned route and I wanted to suggest some changes... I don't yet know the way to get from Brooklyn to LI, I guess in 16 months I'll figure that out when I move into Brooklyn. The north shore can be hilly as mentioned short but steep hills. I'm still working my way back up to hit the 60 and up mile rides I used to do on the north shore... I do have a decent route from Cold Spring Harbor to my place and then beyond. @PatrickGrehan did that route with me I think in February 2020 right before everything shut down...

Do you have a link for the Cold Spring -> Smithtown route? 

http://tpks.ws/ERSDU2EFMIXIMBD5SUITUNLWMY   Try this... I go counter clockwise.

This ride will be 140 miles for me ,I’m slightly worried if this is with hills 

In terms of altitude it only adds 300 meters over the whole thing. We’ll take it easy for sure. 140 miles is far though 😅

Ha , trying to fool me with KM 

HEre's what Myles sent.  Whether or not the ride takes his advice is up to the participants.

That written, do make sure you have his number (it's below).  If things go sideways, he's relatively near and could come to the rescue.  

I also want to reiterate his point about complete tools driving around the Hamptons.  It could be annoyed locals who resent the moneyed weekenders, and it could be those moneyed weekenders who figured they spent oodles to get away from hassles like dealing with cyclists.  Don't expect to have friends in cars out there.    

Appreciate all the advise , but Lads , we are going to Montauk , not heading off to Alaska  

This still happening , looks like a 10mph headwind 

Oof. Let’s see if weather predictions change 

Just do it backwards!

We could take the 7.13 from Jamaica and ride back

That’s actually not a bad idea haha