Explore the best rated trails in Bridgeport, CT, 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 76 trails covering 609 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.
Wassaic to Orphan farm and back will take you through farmlands, marshes a bird sanctuary and a long bridge over the marsh that you must just stop and absorb the place.
A great place to train because you draw strength from the scenery and there is lots of shade and lots of benches along the way.
Have respect for others that are smaller (tricycles or training wheels) and older folk sharing the trail and you will have an outstanding ride / walk / run.
Wassaic to Orphan farm and back will take you through farmlands, marshes a bird sanctuary and a long bridge over the marsh that you must just stop and absorb the place.
A great place to train because you draw strength from the scenery and there is lots of shade and lots of benches along the way.
Have respect for others that are smaller (tricycles or training wheels) and older folk sharing the trail and you will have an outstanding ride / walk / run.
Excellent trail except for the staircase once you get into Brewster from the Danbury area. Why wasn't a ramp put in instead of 2 steep staircases to carry a bike up or down?
The Dutchess County portion of this incredible biking trail is almost unusable right now. Weeds wildly overgrown and sticking out 4-5 feet into the trail on either side. The Dutchess County people responsible for this negligence should be ashamed of themselves.
Can’t say enough well maintained , a must do !
These are really 2 separate trails with a variety of surfaces and a bit of street riding. The Norwalk trail is mostly asphalt going north from the sound while the trail in Wilton has about half going through a wooded area with pea gravel. This is the most enjoyable spot to ride as the other half of the Wilton trail dies out north of town on Route 7 with nothing around. If they were ever able to connect the two routes you would have something.
I entered the trail on Ryder Road in Ossining and ran to the Teatown preserve and back (approximately 6 miles).
The trail is overgrown and not well maintained. There are points that are severely sloped and there are rocks hidden in high grass. Along the trail there is a creak that has stagnant water. The high grass and water leads to a large amount of bugs. I found a tick on my leg after the run.
On the trail there are abrupt up-hills that are not maintained or easy to traverse without coming to a slow walk due to rocks and roots. The scenery is beautiful but the trail needs a lot of love and care.
Manchester towards Hartford is great for a few miles. Then it gets a little dicey and unpleasant. You’re forced onto sidewalks through busy neighborhoods and alongside a highway with only a jersey barrier between you and reckless drivers.
Beautiful needed trail, extending the Dutchess Trail down to Brewster. Pity there seems to be some big ownership/maintenance dispute going on I guess between Dutchess County and NYS? Because right now no one is cutting back the weeds on the Dutchess County side and there’s a big defensively toned sign up saying that Dutchess County is not responsible.
Twice this week I saw a bear x the trail near the USA transfer station.
Also saw two women digging up poppies! That's a no no!
The extended trail that ends by the motor vehicle bldg has beautiful poppies and other ornamentals! Well done you guys!
The map shows a disconnect, but the trail went all the way through. We did the whole trail and although it had a bunch of twigs it was a great ride. Well marked and in very good condition
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