Rode this trail from Rockwell Lane to the Trestle and back Sept. 3 --- the trail was muddy with extensive puddles that were too deep and wide to ride through. As a result we had to do a lot of careful walking the bikes around the puddles in order not to fall in the mud. Riding was made even more treacherous by the heavy and numerous branches that covered the trail and frequently got caught in the spokes stopping the bike and pulling it down! This was a miserable experience. I understand that the branches were left by maintenance crews cutting brush on the sides of the trail, but one would have thought they would clear the cuttings from the trail bed for the cyclists! The part of the trail after the cement works to the trestle was much clearer and less muddy. I think its a shame that the crews did not clear trail of branches. I have never seen a rail trail in such bad condition!

Started at Rockwell lane in Kingston. It was a mud pit. Rode 2 miles and turned around too many sticks, twigs and mud on this section of trail. Doesn’t appear as it’s maintained. Next time I’ll start closer to Rosendale.

Hurleyville has done a great job with their sections. Off the paved sections, much of the cinder trail is OK for cinder, but some could be termed "Narly mountain bike course."
I've done many long rails-to-trails and have enthusiasm for the future for the O&W. If they focus on the benefits of bike tourism by better signage (away from Hurleyville), services, one continuing trail, and regular grading and surfacing (cinder, or better, crushed limestone) this will become a great asset.

First & most important: start in Naugatuck !! Zero parking in Southbury. Don’t be put off off super steep hill - it’s only about 80 yards - just wheel your bike up to the top & you’ll be on nice flat rail bed. First time ride this trail. Had a raw unfinished feel to it. Some steep up & downs at road crossings which were little off putting outbound but on return was expecting them & didn’t even have to dismount for 3 out of 4 of them. One section like riding a dry river bed - take it slow or walk - only 200 yards or so. Sone areas muddy and would be messy after rain. Despite unfinished feel was well maintained and even huge fallen trees had been cleared. Very peaceful ride. I have hybrid bike regular tyres not fat ones.

Enjoyed this ride with our 10 yr. old daughter and she was thrilled to bike on this trail.. competed the entire trail of 7.6 miles.

easy, beautiful, peaceful, friendly, shaded Great for walking and biking

On the top of the hill there is a small shack on your right. If you are approached by anybody asking you for a pass or to purchase a daily pass for $20 it’s a scam!!

Nice trail bed (not for rode tires), I wouldn't ride anything thinner than 38mm on a drop bar. Short punchy climbs on either ends other wise fairly flat river side riding. Has a nice flow and is not heavily used. Access to the River via camping areas or launch areas are throughout the length of the trail. A short section of single track between Namanock Island & Raymondskill road is not recommended for bikes (both locations have trail access via parking areas). Route 209 has a decent shoulder between these 2 points so you can ride the road. A fun way to check out the river or pound out some miles without worrying about cars.

The trail is absolutely beautiful and feels like I can etc with nature with a quick getaway. I used my under armour tracking app to guide my run. Sadly the trail itself is not 3.2 miles. It runs approximately somewhere in the 2.8 region. That’s joule be corrected. Aside from that, I think I’ll be running this trail very often.