Looking for the best trails around Holbrook?

Explore the best rated trails in Holbrook, 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 59 trails covering 403 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.

Recent Trail Reviews

North Shore Rail Trail

ok ride

November, 2022 by senseibarb

Yes the path is new, surrounded by greenery and tuck back from the main road. My biggest complaint is the amount of crossroads at the beginning in smith town. Too much interruptions AND You really need to be careful even when you hit the rider alert button for crosswalks The ride itself is nice, but no facilities on path.

North County Trailway

beautiful & well kept trail!

October, 2022 by 9kw466jjyr

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.

Bronx River Greenway

Nice trail

October, 2022 by dd5rz2q65y

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.

Accordion

Larkin State Park Trail

Two very different trails in one...

October, 2022 by shannon66

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.

Farmington Canal Heritage Trail

Very nice

October, 2022 by dcsnyder

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.

North Shore Rail Trail

Great Ride

September, 2022 by youallredeno

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

North Shore Rail Trail

nice trail

September, 2022 by david semler

Very nice fully paved trail. Saw some gophers and deer along the way. Maybe an eagle too but not sure. Might have been a hawk or a vulture. Parked at senior center as recommended in the trail information section.

Bethpage Bikeway

Bumpy Ride

September, 2022 by senseibarb

I’ve downgraded my previous review to four stars. I rode the trail yesterday morning, and while it is still a great workout the trail needs to be repaved in several areas. The patchwork that was done is not even with the results making for a bumpy ride in several places. The massapequa side and Bethpage side is flat and smooth. It’s the middle area of the trail that gets a bit rough. Not good for the bike or the butt. Hopefully this can get corrected as the scenery and length make for a stunning ride !

Maybrook Trailway

Nice Smooth ride

September, 2022 by borchardtdebra

I parked at Pumphouse Rd which is right before the Tonetta Lake parking area. I rode north past Tonetta and up towards Patterson. Not too many people maybe because there was a warm summer rain that felt pretty nice. The swamp was huge and there were lots of historical signs. I’d definitely go back as this was my first time to try it out.

Setauket-Port Jefferson Station Greenway Trail

Great bike path

August, 2022 by atgavin1

3.4 miles out. Wide path for bikers and walkers. Hilly throughout trip. Lots of shade and quiet.

Maybrook Trailway

Pretty, shady, flat. Connected to Duchess Rail Trail and went all the way to Walkway over the Hudson.

August, 2022 by krce4

Pretty, shady, flat. Connected to Duchess Rail Trail and went all the way to Walkway over the Hudson.

Maybrook Trailway

Very very nice! Goes into CT

August, 2022 by tm070958

I rode south then east from rt. 8 in Poughquag. There is a small missing section above the Croton River east branch in Brewster . You can walk your bike along RR, via open fence for this 50 yards or so or cycle downhill on Peaceable Hill rd and up the hill on East Main to get back on. The TrailLink map (as of 8/3/22) shows the trail ending here. But it continues a few miles east into Connecticut. About a half mile over the line to an overpass at Mill Plain Rd in Ridgefield CT. Smooth all the way with terrific scenery. Many lakes.

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Accordion

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