Biking on Shelter Island

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Anonymous's picture

I am visiting Shelter Island on Labor Day weekend and looking for some guidance:

I want to take my road bike b/because I've heard it's fun to bike around the island--but if I do that, I can't take the train from Manhattan since bikes aren't allowed on the LIRR Friday and Monday of that weekend. The bus from Manhattan allows bikes, but the bus doesn't seem like as good of an option due to probable Labor Day traffic.

Perhaps someone out there has biked on Shelter Island and could tell me whether its worthwhile to (fight the traffic and) bring a bike?


Anonymous's picture
Russ Berman (not verified)
It's a lovely but not exciting place to bike

Like most of the farther parts of Long Island, Shelter Island is generally pretty flat (you can find a couple of steepish short climbs around the Heights area near the golf course). It's also much more relaxed and traffic free than the Hamptons. Trouble is getting oriented and working out a continuous route beyond the very pretty run over the causeway to Ram Island and back through Deering Harbor then over to the South Ferry (to Sag Harbor)--which I've never managed to extend beyond 15-20 miles out and back. (I've tried it three times in the last couple of years, without a map, and always wound up retracing my route somewhere.) If you're looking for a longer ride, I'd hop the ferry and continue on 114 to get onto the Montauk Highway east of Amagansett (see posts of the last week or so on how to get to the highway without going all the way into East Hampton on 114)and continue on as far as you like toward Montauk/Montauk Point and back.

Anonymous's picture
bill (not verified)

It's very pretty to ride there. If getting your bike out there is a problem, perhaps you could rent a bike? There's a bike store in Sag Harbor on the South Fork and one in Greenport (North fork) and both are less than 1/2 mile from the ferries that go to Shelter Island.

I wouldn't say Shelter Island is totally flat but it's not that hilly. A hybrid or even a singlespeed would be fine. It's not a real leg stretcher of a ride. Probably more fun to ride, stop, swim, eat, drink...

Anonymous's picture
Ron (not verified)
Biking on Shelter Island

There is a group from Bike Hampton in Sag Harbor that rides Shelter Island on Sundays in the summer. They leave the shop around 7 Phone: 631.725.7329, E-mail: [email protected]
Rotations in South Hampton has a map
happy trails the only sane alternative is on two wheels out there!

Anonymous's picture
April (not verified)
Maybe, maybe not

"Really depends on what you have in mind as far as ""riding"" goes. Shelter Island isn't that big, as pointed out by others. I used to live out near that end of LI and had riden Shelter Island many times. I think I pretty much covered every feet of cyclable routes! ;o) Lovely as it is, it's at most a half day riding to cover most of the island. That's all. I would hardly consider that ""worthwile"" for missing the train.

On the other hand, you can take the ferry to Sag Harbor to extend your route. There're some nice, quiet back roads in that part, too. You can also ride all the way to Montauk and back. I've never biked that segment on a holiday weekend so I can't say whether the traffic will be a problem or not. When I rode it mid-week, it's gorgeous!

So, if you plan to make this a biking vacation, by all means take your bike with you. If, on the other hand, you're just doing a little bit of riding during your otherwise non-cycling holiday, I'd leave the bike behind for another time."

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