Find the top rated hike trails in Winchester, whether you're looking for an easy short hike trail or a long hike trail, you'll find what you're looking for. Click on a hike trail below to find trail descriptions, trail maps, photos, and reviews.
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We were looking forward to this ride a long time as reviews rate it highly. For us it was quite the opposite. The trail did have its moments and from the start looked very promising, however those moments were short and far in between. The first of the issues were the trail closures with no notice at trail heads or reroutes. You merely run into a blockage where your only option is to turn around load up your bikes, go a couple of miles to the next bike parking, unload, ride a couple of miles and hit another trail block. Second issue, the trail is poorly marked. We literally spent more time trying to find our way through Chattanooga than riding our bikes. Trail Link helped but what a mess. I can’t imagine riding this trail in peak season as it was, our ride early Feb, 50 deg late morning saw many pedestrian obstacles. Chattanooga is a busy place, a nice city to be sure along with that comes constant traffic noise.
The trail from Sewanee to Tracy City is all asphalt now which is about 12.5 miles. The only caveat is you must ride in the bike lane on the highway that goes over I-24. If you’re coming from Sewanee look for College Street that runs parallel to the highway after you cross the bridge. It basically dead ends into the trail. Beautiful trail, about 70% shaded, inclines are very modest.
Dropped in at Barfield Road trailhead and headed up, 15.3 miles out and back on a beautiful summer day. Cicadas were loud and the birds were singing! Our first time on the trail after reading all the reviews and we loved it! Every city in America should be made to put in one of these to this caliber. Murfreesboro should be proud! Lots of people enjoying this day.
We rode the entire pathway, starting at the northern dam site. This is one of the most enjoyable, varied, and well maintained routes we've ridden! The entire route is well done, with light poles the entire way, elevated sections or bridges thru all types of natural areas (instead of around), and many parks or trailside restrooms. Whether thru parks, alongside the highway, or even past industrial businesses, the trail is landscaped O meadow-scaped), the path is smooth, and
Today 4-17-2025 my husband and I rode the trail from the Wheland Factory parking lot to the Dam. The first part of the trail goes past some industrial areas. As we got further up it goes past townhomes and downtown. Our only complaint was the lack of trail signage to keep you on tract and mileage markers. There were some metal cutouts with numbers indicating the miles and some very small markers in the concrete itself with markings but unless you stopped to read them, there was no way you could have read them as you pedaled by. The trail itself is in good shape and we saw several crews keeping the grounds surrounding the trail trimmed.
They have built a very nice bike path that connects the middle and the southern sections along Bailey Cove Road. There are also lights at the crosswalks. Thanks!!
From the Kingston Pavilion at Ditto Landing, cross the bridge and walk north along the river. Also suitable for gravel or mountain bikes. About 60% shaded. Beautiful walk.
Rode from the bottom TH all the way up and back again. Gravel bike did great. Enjoyed the scenery and history. But the trail simply dead ends on a busy road. I took the road up higher on Lookout Mountain, but was not worth the extra ride.
The multiple boardwalks and intermittent views of the creek are what make this trail a 5*. As noted by another reviewer: A large section of trail is CLOSED until July 2027. If you are coming from Camp Jordan and heading north, you cannot cross I-75. But the 11 miles of trail north of I-75 to downtown Chattanooga are open. I parked at Sterchi Farm TH and did some out-and-backs. The best scenery (ie, the boardwalks) are north and south of Sterchi Farm TH.
The construction south of I-24 is done. You can now get all the way south to Barfield Park.
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