Find the top rated horseback riding trails in Wilbraham, 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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This trail was OK. The part along the river and in downtown was scenic and it was paved all the way.
However, it goes along the highway for a while with just a chain link fence as separation, which is not enjoyable at all (east of the gap is not scenic). It also has a lot of tree roots creating speed bumps. Finally, the gap between the river and the rest is significant (& don't take what looks like the most direct route as Pratt & Whittney has a security gate for part, so you can't get through unless employed there).
Went north out of Keene on the trail, and was quickly in a lovely wooded area, then soon at a side trail to Stonewall Farm, where visitors are welcome to wander. The birds were singing happily! We did 6.5 miles out before turning around but there was plenty more trail to explore. If you are expecting a super flat trail and a packed surface this may not be your kind of fun. If you don’t mind dismounting for a rickety bridge, or adventuring on side trails, then check this trail Out ,
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.
Currently there is a couple of sections that are really nice for the work thats been completed, but will be a fantastic trail once they have completed the sections necessary to connect them into one long trail. All the sections completed are mostly all paved and are great for walking/jogging/biking & wheelchair/stroller friendly. The only exception is tgr Naugatuck River Greenway section that starts at the Sullivan Senior Center, which has a paved trail that runs parallel to the the river and ends at the side road which you continue down a one way street that almost zig zags until you reach palmer bridge. Crossing the bridge and crossing to the paved trail that goes behind a condominium and continues until the end of the dirt parking lots (trail is paved) of John Toro Sports Complex, where the pavement ends towards the actual field. Then it transitions to the field with no defined trail. The Trail at that point isnt really distinct. I lived here most of my life and I didnt know until I saw a news article about The Rainbow Bridge and found that the trail in fact extended past where the pavement ends and continues straight past the dog park past both the first baseball field, the soccer field, and then about halfway through the 2nd baseball field there is a wide opening in the forest, where you then see the entrance to the Rainbow Bridge Trail. Which is an amazing small half looped trail, with some of the most beautiful works of art, and tributes to various pets (photos, stepping stones/memorial rock garden, a memorial fence, k-9 officers memorial bulletin board(s), sculptures, poems, signs, chairs, then the rainbow Bridge which is adorned with photos, momentos, stories, collars & tributes to pets of those who came to place their beloved pets memorials. After you find the exits shortly after that you can see the wide open pathway continues for a while on but ends at a fenced off area that currently is a business/underutilized "Sports park" that will eventually be replaced with a connector trail that will connect with other nearby trails.
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.
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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