looking for routes around Eastern Long Island

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Anonymous's picture

I'm looking to do some riding around the eastern end of LI. Ideally I'd like to do around 75-100 miles. I was thinking about starting near Greenport and perhaps doing a loop around the Peconic including going out to Montauk Point. I'd start by heading West on 25. But I'm not sure the best way to get from 25 to the South Fork and from there, a safe route to Montauk.

I know the North Fork roads but am not sure about riding on the South fork at all. Anyone have any trip routes that start around Riverhead and go to the lighthouse? Do I just take Montauk HW all the way to the end?

I looked at the two Montauk rides in the library but am not sure at what point I'd join into them. Also, I'm not sure the best way to get from the North to the South fork.

As for heading back to Greenport, I'll take the ferry and go through Shelter Island which I know pretty well.

Thanks for your suggestions.


Anonymous's picture
j (not verified)
LI routes

I once did the Bike-Boat-Bike century which goes from Mattituck to East Hampton and back, but it was awhile ago and I'm not sure of the exact route. Get yourself Hagstroms Eastern Suffolk County map from BN and you should be able to put together a good route. I just did some nice riding from Bridgehampton to Montauk and found it key is to stay on the backroads North and South of Montauk highway as much as possible.

Anonymous's picture
al stern (not verified)
riding on eastern long island

I do a ride similar to what you're looking for. I start out on the North fork in Peconic and take truck 25 (Route 48) west to 105 south. There are asome local streets that continue from 105 that go directly into Montauk highway (Route 27 at a certain point.)(Consult hagstrom, eastern suffolk for street names). From there I head east to Montauk point. On the return, I head west on Montauk highway (again 27 at a certain point) to 114 north to catch the ferry to Shelter island and then I take another ferry to Greenport. From Greenport I head back on main road to Peconic. This trip exceeds 100 miles. Get a hagstrom map of eastern suffolk county and you'll be in business.


Anonymous's picture
bill (not verified)

Thanks! That' basically the exact route I've been thinking about. My folks live in Southold.

On Sunday I drove on 105 to 104 which interesected with route 27 - it didn't seem too bike friendly. 105/104 was like a highway. Is that the way you got to 27? I didn't see any riders on it. If possible I'd like to find a slightly safer route for that part.

As far as 27 goes, did you take that all the way to Montauk? Did you take the Old Montauk Highway at any point? I remember that being a nice hilly road. But if the total trip length is already over 100 miles, I might not be able to afford the strength to mess around out there. Any idea how much more than 100 miles you rode?

I have a bunch of maps from AAA but the problem is some roads that look to be local, such as 104, are actually kind of hairy. And I have no idea what to expect on 27.


Anonymous's picture
al stern (not verified)
east end rides

There aren't many riders out there but I ran into one on may last trip out which was this past July. 105 is the only way you can go South. I've done this trip the past three years and the first time i did it i took 104 but much of the shoulder was rough or not paved very well. I believe there was construction going on at the time. I heard they paved it but I thought it was a little busy. What you should do is when you see the sign for 104 ignore it. Keep going and 105 ends and then there are some local streets you'll go through which are basically continuing in the southerly direction. (Straight from 105) and if you follow carefully you'll hit Montauk highway. You'll pass some farms on the way, you'll also go over some railroad tracks which i believe are LIRR. AAA maps do not show the names of the streets that will take you to Montauk highway. You need to get Hagstrom's map of eastern suffolk. I strongly recommend this map and carry it with you on your journey. Old montauk highway becomes 27 at some point. It gets a little tricky but if you study the map you'll know what I'm talking about. The total distance back to peconic was about 115 or so. At greenport I believe was slightly over 100.

Anonymous's picture
bill (not verified)

FYI, someone from the Suffolk Riders association send me some maps of a couple of great routes out there. One is a 60 to 135 mile route around the Peconic - exactly what I've been looking for.

Anyone interested should email me and I'll send them the PDF's.

here's a link to the suffolk riders assoc: http://www.sbraweb.org

cycling trips