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Port Jefferson to Orient Point

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Port Jefferson to Orient Point

Old 03-08-21, 07:32 PM
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Port Jefferson to Orient Point

I did two rides on Long Island last year, Orient Point and Greenport area and Port Jefferson to Fire Island and back. A few of us are looking at a century ride starting in Port Jefferson to Orient Point and return, almost all of it on Route 25. Any suggestions or tips? We planning to make a lunch and coffee stop along the route.
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Old 03-09-21, 04:07 PM
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I biked out that way a few summers ago - covered the eastern part of your planned route with comments here. Biking around Shelter Island?

I think you'll possibly enjoy it more if you can stay parallel to 25 where possible instead of on it.
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Old 03-09-21, 07:46 PM
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Here's a ride I did in 2015 from Port Jeff to Greenport. I'm going to reprint it exactly as I posted it here or somewhere else back then.

This route is longer than it has to be, only because I would rather ride quiet scenic roads than main arteries like Rt. 25 or Rt. 25A. That said, this was a perfect plan for my first ride between Port Jefferson and Greenport. However, next time, I will probably modify it to include more places to stop for lunch, water, or rest. Perhaps I will hit 25A a little sooner and cut out a big chunk of Sound Avenue.

If you choose to take this route, be sure to carry a good amount of water, and maybe even your lunch or some snacks. I rode it on a Sunday, and not a lot of places were open to eat. For water, I needed to keep stopping at farm stands and slithering my way through tourists to pay $2 for a small bottle that was dry before I left the parking lot.I will also mention that Greenport has at least one public restroom, where you can wash up and change clothes once you get there. I am very glad to have brought a change, because the train leaving out of Greenport (there is only one on Sundays) was packed and I would have felt very uncomfortable riding with all those people if I were still covered in mud and road grime from the ride. (Oh, did I mention that I got poured on for the first hour of the ride?)

Here’s how I planned my trip:

Take the LIRR to the Port Jefferson Station. This leaves you in a not-so-great part of Port Jeff, so don’t expect the quaint, scenic village that is just down the hill.

Riding away from the front of the station house, turn right to head north on Main Street. Just before the road starts to head downhill, turn right onto North Country Road. Take N. Country ~3.5 miles and bear left onto Lower Rocky Point Road. You will be riding through a quiet neighborhood with some nice houses and you may not see a car or a person for quite some time.

After ~2m, bear right onto Rocky Point Landing. Continue ~2 miles and turn left onto N. Country. At ~ 1 m (Choice Neurology & Chiropractic), N. Country becomes One-Way for about a block. Unless you want to be a scofflaw, bear right onto 25A for a few hundred feet (?) then make a quick left to get back on N. Country.

Proceed ~2 miles to a duck pond on the right, a smokehouse restaurant on the left, and the boundary marker for the Town of Riverhead. You are now heading into Wading River. Bear right at the duck pond to stay on N. Country. At ~1.5 m (near end), turn right at Debbie Lane and turn left onto 25A, just long enough to make your very first left onto Sound Avenue. (Note: This is not the “Sound Road” that you passed back at the fork in Wading River, so don’t go looking for short-cuts!)

Sound Avenue (aka Middle Road & Rt.48) will take you past 25 miles of wineries, farm stands, and open fields, plus the "famous" Briermere Farms, a popular place to stop for pie. At around 23 miles, there are some water views, but not for long. I turned right at Moore’s Road to get to Rt 25, then left to get into the village of Greenport, but this is only because I always wanted to explore a bike path that goes through the woods there. A more impressive way to enter Greenport is by continuing on Sound Avenue another ½ mile or so and then turning right onto Rt. 25, which will take you right into the heart of the village. 2021 NOTE: To continue to Orient Point, stay on Sound Avenue all the way to the end. If you have time, take the two-mile turnoff to Orient Point Beach, a great, relaxing spot with restrooms, vending machines, etc.

If you’ve never been to Greenport, you will be pleasantly surprised by the scene taking place out there in the summertime. The rest of the year, there’s hardly a soul on the streets, and they roll up the sidewalks at 5pm. There are several places you can pull your bike right up to a table on the sidewalk and have a decent lunch or dinner, and the boardwalk adjacent to the marina is a perfect place to grab a bench, gaze out at the harbor, and enjoy a great breeze. A short ferry ride from here takes you to Shelter Island, and another ferry on the opposite side of Shelter Island takes you to North Haven, which you can ride to Sag Harbor and The Hamptons, if you have energy left in you.

Overall, though the last 10 miles or so got a little tedious, this was an excellent ride that I will probably add to my annual summer roster. I recommend giving it a try.
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