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Explore the best rated trails in Woodbury, CT. Whether you're looking for an easy walking trail or a bike trail like the Hudson River Brickyard Trail and Walkway Over The Hudson. With more than 73 trails covering 548 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.
Road part of 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 (25 on the Farmington Canal Trail).
The trail is in very good condition. The transition to the Southwick Trail at the CT/MA border (with no road crossing) is seamless.
Road crossings decrease as you head north and are well marked with push-button warning signals to alert traffic.
Half Mile Falls Park at the north end of the Columbia Trail in Westfield is definitely worth a stop!
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.
Fantastic ride, very smooth well-maintained. Enjoyed the views and shade with my wife. Recommend for novice bike riders.
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!
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.
4/21. We parked at the Beardley Zoo parking lot and biked only 1 mile until we couldn't go any further. There was flooding and construction was taking place for a new water pipe. So we had to go to our car and start somewhere else. We parked on Trumbull Ave. at the Dept of Parks and Recreation as the parking lot for the trail on Trumbull was closed. We biked about 5 miles to Whitney Ave. and there was another sign that the trail was temporarily closed. The 5 miles we biked were lovely along the river. I'm not sure who you would contact to find out the status of the trail. We were hoping to do 26 miles round trip and got in 13.
I'm slowly checking trails that make up the Empire State Trail off my list so I will compare the Putnam Trailway to its adjacent trails.
Both the North County Trailway and Maybrook Trailway offer a better riding experience in my opinion. They are both slightly longer, are a little less hilly (which could be a positive or a negative) and are in better shape. All three trails provide similar scenery with a good mix of residential, tree cover and a few lakes/revivors.
That being said the Putnam Trailway isn't a bad trail by any means. It is hillier but that breaks up the monotony of a flat trail. Some of the hills are a fair challenge but they are not very long so its a few short climbs followed by a exciting downhill. There are a fair amount of road crossings especially around Baldwin Place but only two or three are busy, the rest were very quiet. I would say the roughest part of the trail is also around Baldwin Place, nothing crazy just a few bumps and cracks. I have a hybrid bike and had no issues with the trail.
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