Explore the best rated trails in Port Chester, NY. Whether you're looking for an easy walking trail or a bike trail like the Norwalk River Valley Trail and Ridgefield Rail Trail. With more than 92 trails covering 600 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
I mountain biked this short but beautiful trail before the 2012 Sandy washout. I took it from Ogdensburg to Beaver Lake Road (walk the tracks the last 300 feet) and then headed down RT 23 and left on 517 to Ogdensburg for a easy loop ride. I hiked the trail 1/13/2023 and I am happy to say that the collapsed section now has a narrow berm on the south side that can be biked (technical) or just walked. There are some trees down along the trail (hop some and carry over some) and some muddy areas by the rock cuts and some passable streams, but the views are worth a try. If you scramble up the rock mound you have great views of Ogdensburg and Sparta, and when you travel under the power lines you have a great view of RT 23 and Franklin. I think the rock cuts are deeper than the ones on the Paullinskill Trail and the elevated rail bed section are amazing. If you want to continue further into the Hamburg Mountain Wildlife Area, you can hop off this trail when it gets close to RT 23, and you will be across the street from their parking area. There is a also great little convenience store at the start of the trail in Ogdensburg as well a a new local bar across the street.
I’ve completed the Wilton trails in Lovers Lane, Entrance near Orem’s Dinner and Mathews Park. All are great. My favorites are the Wilton Trails, you enter and your engulfed in nature. Absolutely beautiful. I also love walking In Mathews park although that is more of a city trail to me not as much nature as these are concrete paved and you pass near traffic and such. So grateful to all the hard work put into to providing these trails thank you!
Beautiful bike trail to enjoy the fall colors. Love it so much. Highly recommend.
This trail is well marked and is a great combination of climbing steep rocky sections and walking flat sections with decent views. For someone out of shape, this hike is a great workout with plenty of resting spots.
This trail is great despite the middle aged men speeding past you at 90 mph on their LeMonds. I’m not sure if they are bike messengers or just “has beens” trying to live out their dreams of being in the Tour De France, but their speed and shrill shouts of “Left, Left, Left!” piercing the crisp fall air can really ruin what is otherwise a beautiful and relaxing family outing.
Nice trail for running, and it wasn’t too crowded. There were a few scenic areas but I was expecting more. Also if hilly around the start. And decent parking.
Although it's an easy, beautiful, and relatively flat trail overall, the Naugatuck-to-western-outskirts-of-Naugatuck part of the Larkin Bridle trail is a little more challenging, isolated, and wild, whereas the west-of-Naugatuck to Southbury part of Larkin Bridle is wider, flatter, and more accessible.
Personally, I am not big on technical/single track bike riding, so I experimented with Larkin Bridle until I found just the right section to become my regular ride. For me, that's definitely the flatter, wider, less technical portion. These coordinates (41.474814, -73.117086) will take you to a very quiet, non-residential road with a turnout that allows for three or four cars to park in front of the wide gate that marks the path. (There's a marshy pond nearby where you might hear ducks quacking.) This is the point on Larkin Bridle where it become an excellent trail not only for comfort-minded fitness bike riders like me, but also a great walking path, especially for my dad, who is older.
From the coordinates above to Southbury it is about 5.5 miles, one way. You'll be on a wide path with a mix of hard pack dirt and gravel. Very easy and flat, unless it's been raining for a few days, in which case some parts can get a bit muddy. Overall, this part of the path is shady and well maintained with beautiful, tall trees, occasional bodies of water, and interesting rock formations. Just gorgeous! On this part of the trail, you can relax and pass people easily. Would be wonderful for a post-Thanksgiving dinner walk or a ramble with the dog. The Naugatuck-to-western-outskirts of Naugatuck portion of Larkin Bridle, by contrast, while still very doable on a bike, is much more weedy, woodsy, and rocky, with brief portions that have very steep ups-and-downs near road crossings. For a more relaxing experience, I recommend the west-of-Naugatuck to Southbury portion, starting at the coordinates above and heading toward Southbury.
Went on OCT 6 on an absolutely beautiful fall day. The trail is easy but there are so many side trails and that you keep riding through Sea Breeze that we put in 18+ miles in two hours. Lots of access to virtually empty beaches on both sides of the peninsula for relaxing and fishing. No swimming though. We plan to come back to not only ride again but to bring the beach and the fishing gear. It is a gem in one of the most highly populated areas of the US.
Rode Plainville CT to CT/MA border. Northern section. I like that you go through many towns on the lower half then out in the country from Simsbury north. Beautiful scenery. Paved the whole way, some sections with roots coming through.
Paved trail, it’s clean, 10+ miles long. Well maintained. Great views and you may see turkeys, deer and ground hogs/ gofer not sure what they were. There are bugs out that will hit you in the face and stick to your body will riding
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