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.

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!!

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.

This was my first time on this trail and it is worth the trip. It is well maintained with a few bumps here and there but nothing to worry about. It is “flat”, but there is an incline to it. The trail from the southern end in Wassaic to Millerton is 11.5 miles and the trail rises 250 feet. So that’s about a .5% incline which is nothing over a short ride but you do feel it a bit over 11 miles. Well, at least my 61 year old legs felt it a bit. Maybe 2/3rds of the trail is under a tree canopy which shades you from the sun on a hot day and provides some blockage on windy days. If I counted correctly, there are 10 road crossings, which works to less than one per mile. And most of the roads are rural roads so you don’t have to stop too frequently. Though the driver of the one car I encountered didn’t even let up in the gas, let only brake or stop. The restrooms in Millerton are closed, I assume due to COVID. There are two porta potties along the trail. One minor negative is there aren’t too many benches along the way if you want to stop, rest, and enjoy the scenery. And the scenery is nice, maybe not the nicest I’ve seen from a trail, but it certainly is a very pleasant ride. For a beautiful 85 degree August Saturday, there weren’t too many people on the trail, though there were other riders. And everyone seemed friendly. I’m not positive if I was suppose to park where I did - dirt parking lot next to the trail in Millerton - but my car was neither towed nor ticketed when I got back so I guess it was okay. There’s parking at the southern end plus a few smaller lots along the way. There are no services along the way but Millerton has restaurants and shops by the trail. And I believe there’s a place to rent bikes as well. They are extending the trail another 8 miles or so north from Millerton with an expected completion date of October, 2020. So once complete, you’ll be able to do a 40 mile round trip.

I drove over an hour to bike this trail only to find signs at both ends of the trail stating parking is for New Milford residents only and cars will be towed. Literally nowhere else to park. It was Monday morning and there were only three cars total parked between the two entrances.