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South Side Trails

 3.0 (1)
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Map Key

16.9 Miles 27.2 Kilometers



914' 279 m


-911' -278 m



Avg Grade (1°)


Max Grade (8°)

174' 53 m


38' 11 m


Shared By Jim Butler



Getting forecast...

A hidden gem, although it needs a lot of love and riders to make it better. Can be very confusing and not well marked.

Jim Butler

Dogs Unknown

Features -none-


Most riders park in a small lot on the north side of 114 and go north. Look directly across the road and you'll see the start of this trail network. I have been riding these trails for years and rarely see anyone and after all the years and all the rides I still get lost at times and see new trails that I haven't explored. I will upload other rides that hopefully cover most of what is on the south side of 114.

Need to Know

This ride is just short of 17 miles of singletrack but there are many ways you can bail early if required. Unlike the north trails, the south trails are not in great shape due to limited riding, sand, and occasional motorcycles that eat up the trails. There are a number of trees down that will require you to get off your bike. In the summer, you should expect ticks. Wear long socks, spray them, and stop every 45 mins to check. Bring a plastic bag for your clothing after the ride in case there are any on your clothing.


Now why would you ride this after reading above about ticks and motorbikes? Well, first the area is vast with trails that go in many directions. I like to explore and love to find new routes and trail connections. I like trails where I am alone and not dealing with other riders, runners, or people with dogs. I realize that posting this may change the solitude but I think it would be good for the trail conditions so please come ride and I promise to say thanks!

OK, let's get started... The first stretch is fun and is about one mile before you hit a single lane road that you need to cross. The entrance to the next section is clearly visible so no worries. Once you cross the road, there is a fun downhill and then a climb. If you notice on the map, the trail splits. I like to ride to the left (right segment when looking at the map) and return on the other trail to the left when looking at the map. Why? Making a left starts with a fun climb and is followed by a series of steps that climb and climb.

After about a mile (not sure exactly), you'll come to a four-way. Make a left and after about 100 yards, you'll hit the powerlines. Make a right and be cautious of the sand.

Go past the first power pole and just before you get to the second power pole, there is a small trail to the left. After about 50 yards, stay left when you see another trail to your right. When you come out by a power generator, go straight and you'll see a trail to the right. This will dump you to a road which you cross and continue, heading east, just to the north of the airport.

Next, you'll come to another fork. Head left on what is called the South Loop Trail on this map (no signage on the ground). Continue around this southern loop, returning to the fork to repeat the initial section you just rode on. This time, bear left to head north on the East Access Trail (again, no signage, just called that on this mapping). Here is one spot to bail out as this trail heads up to 114. This ride does a couple loops using this trail and heading west (left) around the Main Loop Trail.

For the second lap, bear right on a Connector just to the north of the powerlines and Old Woods Road. After a sustained climb, you'll arrive at the four-way intersection again. Head straight across on the East Hampton to Sag Harbor Trail heading west and then turning right toward the north. This will begin to descend and curve slightly to the right (east) before crossing over to the Paumanok Path: East Hampton to Northwest Path section, which you took on your way in. Retrace this section back to the start.


Land Manager: Town of East Hampton, NY

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in New York


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195 Since Feb 24, 2018
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