Explore the best rated trails in Portland, CT. Whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Niantic Bay Boardwalk. With more than 56 trails covering 425 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.
Starts off a little rough! Then it is one of the best trails around!!!
This trail was a lot of fun! Very easy to pedal on it!!!
Road this trail as an out and back in conjunction with the Farmington Canal Heritage Trail and the Columbia Greenway RT from Avon, CT, to Westfield, MA, an approximately 50 mile round trip.
The trail is in excellent condition. The transitions to the Farmington Canal Trail at the CT/MA border (with no road crossing) and to the Columbia Greenway RT on the north are seamless.
The mileage markers are great!
Half Mile Falls Park at the north end of the Columbia Trail is definitely worth a stop!
Road part this trail as an out and back in conjunction with the Southwick RT and the Columbia Greenway RT from Avon, CT, to Westfield, MA, an approximately 50 mile round trip.
This trail should be a 5 but it is closed at Main Street in Westfield with no information on when it will reopen or detours.
I got onto the trail at Southbury. I parked at IBM since there was no parking at the trailhead, and got a nice (?) note from security on my windshield. The first half mile from Southbury is very verdant and marked by nice wild phlox, but the path was so narrow you had to watch your feet instead to try to avoid the poison ivy. It widens out once you get to the rail trail. We saw a heron and a deer. A woman on horseback said the heron is famous for trying to scare the horses, they call it the "Pterodactyl". The trail seems to disappear once you get to some of the cross roads and is hard to find again.
I just rode this trail, again. I pleasantly surprise that the trail has been extended about 3/4 mile and now goes up to motor vehicle office in Winsted.
Really liked this well maintained trail. Great views with picnic tables along the route. Wish is was longer.
Was not expecting trail to be as nice as it was. Rode from southern trailhead to Millerton about 12 miles one way. Great views of farms / hills / streams/ wetlands all along a nicely paved trail. Planning to go back and complete the remaining 13 miles north of Millerton. And by the way thank you to Millerton for the excellent bathroom facilities!
This was my first time at this trail. I took the reviews to heart
and chose to park at the Horgan Elementary School lot (near
some Tennis Courts and the Red Caboose!).
Despite out-of-state plates, I had no challenges parking. No stickers or anything were required and
the parking area felt safe.
I chose to Rollerblade on the trail WEST to the End in Coventry.
The first 2 to 2.5 miles are not-so-pretty. It is very urban...some "small" tent out-croppings
along the right-hand bank of the river -- and very industrial....
I kinda wondered why I was there (though felt safe).
The pavement had some bubbly spots and the wooden bridges are a bit course on Rollerblades (keep your momentum up and you can get right across them...or stop fully and take in the views...)
But after you get past the "urban" areas...the trail West toward Coventry REALLY begins to shine. It does have a gradual upward slope most of the way, but seriously quite doable. The quality of the pavement gets better and better and there was only very minor debris on the path. A VERY good path to Rollerblade!
I chose to Rollerblade on the RIGHT side going in both directions, so as to not have to square off with any fast moving bikes. Everyone on the path was VERY warm and courteous!
The major part of the path through Coventry is truly gorgeous...and well worth the ride!
I confirmed with MANY bikers that the stretch EASTWARD to Cranston is NOT suitable for Rollerbladers...Many of the bikers said that it even stinks for bikes actually!
So, the segment from the Horgan Elementary School to Coventry (sort of going "RIGHT" on the trail if tennis courts are behind you) is the place to go!
Couple more things:
There do appear to be some VERY nice parking areas a bit further into Coventry and one MIGHT be able to skip the first 2-2.5 miles of the trail and park just a tad bit closer toward Coventry....That 2-2.5 miles is kinda "crummy", so you're really not missing anything. I don't know the names of those parking areas -- but did not see any signs saying "Residents Only" or anything.
Also, the GENERAL STORE at the very far end of the trail in Coventry is no longer open...so don't plan on getting water or anything there. There ARE a few gas stations one can see along the trail and the very cute ice-cream shop that many have mentioned, as well!
Lastly -- the trail does end very suddenly, when you reach the end in Coventry and there is a Map/Sign that seems to imply that the trail continues into Connecticut....That apparently is NOT true "yet"...but is being planned.
When you look on the backside of the Granite Mile Markers (heading West), they will IMPLY that that you have like 4 or 5 miles MORE to go, but you will hit the END of the trail at around Mile Marker 4.7 -- so it appears that they FUTURE proofed the Mile Markers and included the distance that WOULD be there if the trail did continue into Connecticut.
Several bikers said that one COULD continue into Connecticut via the very busy looking road. I chose not to, being on Rollerblades.
If you are close to Coventry -- start at the Coventry end and blade/bike/walk/run all the way toward the other end -- and simply stop and turn around when it starts to get "uglier"...the final very, very large wooden bridge may be a place to stop and turn around.
Anyway -- it was a GREAT experience...but that first 2 - 2.5 miles from the Horgan School West toward Coventry is a tragic sort of area...the trail itself is okay, but as you head West, you will see what the 5-Stars are all about!!
Enjoy!
Has many crossroads with limited sight distance that affects safety for both the user and vehicular traffic. Town needs to clear overgrowth.
Nice cool day to ride from the Chaplin area up to Putnam. Beautiful country with few other folks. 16 miles each way. Trail was in good shape with just a few wet areas. Some nice newer bridges and tunnel for bigger road crossings. A few areas with larger gravel. Easy to go from trial into Putnam for food. Also a nice bike shop in Putnam.
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