Find the top rated horseback riding trails in Ware, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.
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The Canalside rail trail is fully open and the paved trail is very well maintained. While it is only 7.2 miles round trip, it’s worth it! Plenty of parking at both ends and the town of Turners Falls has a nice selection of restaurants and shops.
We’ve biked this many times. It quickly takes you from Lowell, with its National Park, etc to countryside and the center of small towns along smooth, paved, well-maintained trail. Nice to swim in Hart Pond, too, in season, on return trip to Lowell. Trail keeps getting better and better, great facilities along the way as trail is extended.
This trail needs open parking spaces! Most of the parking spots are blocked off!
Well, used multiple vehicle vehicles. Maintenance vehicle working on trail . Good views. Will ride again.
This is a multi use bike trail for everyone to enjoy.
Rode a portion from Milldale north to Southington. All paved in fairly decent shape. A few bumps but no broken pavement. At the point in Southington the trail just ends with no information as to where to go. No signs or arrows. The trail picks up somewhere a few miles away but I couldn’t find out how to get there. On the portion I rode it was flat and easy, but not much to see other than woods and backs of buildings.
This is a good trail, but if you start in Milford and do the entire checkmark there are a lot of street crossings. The pretty parts of the trail are nice and shady and wooded, but there is a fair amount of commercial areas that you have to get through. It’s nice and flat and there are lots of parking areas along the way. My gps did not take me to a parking lot but when I put the trail into AllTrails I got accurate directions.
We rode to the end of the trail, then continued on Rice Farm Rd. to the dangerous intersection. we missed the entrance to the trail on the way back, so got a good workout on some hilly spots on the road.
On the packed sand patches, keep an eye out for roots that can be a bit dicey. In some spots along the gravel sections, the gravel can be a bit loose, so pay attention to the trail.
First time and loved it! I rode the entire route, starting at the south end parking lot. (42.758592, -72.471175) This trail has some unique features and the scenery is beautiful as you ride next to the river and through the woods. As a former rail, this trail has nice and gradual elevation changes and has fun bridges, which all seem to be maintained well.
At the time of my ride (end of Aug, '25) there were a couple of detours around mile 14 and 16 (heading north) but they have good (not great) detour signs listed to continue the route with a short road detour. As some folks mentioned, there are a few areas that look like they would be pretty wet during the wet season, but I had no issues with any area of the trail and never had to stop for downed trees in the way.
I rode my gravel setup (no suspension, 35mm tires) and had a blast! I'd highly recommend the trail and hope to be back for another spin soon.
Was visiting the area and am so happy I got my gravel bike out to do this trail. As others have mentioned, it is very, very well maintained and quite smooth, enabling fast riding (I rode the entire trail as listed). As a former rail, this trail has nice and gradual elevation changes and has cool features like the tunnels and bridges. I'd highly recommend and hope to be back for another spin soon.
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