Find the top rated horseback riding trails in Hillsborough, 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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Trail lacked any evidence of maintenance. Rode from Hinsdale to Winchester.
I haven't been on this trail for a few years so was disappointed to find there is still an issue with bumps from tree roots and small sink holes. I did not do the entire trail because of this. It is too bad because it is a nice trail.
Pleasant ride on this crushed stone surface, using my hybrid. Very short section that still has rails and ties and requests that bikes go around on the sidewalk, but easily joins back up to the actual trail after about 100 yards. The eastern end terminates in the Squannacook wildlife management area, with walking trails to follow down toward the river. If you are looking for a nice short ride that's under 10 miles total, this is a good one to choose. Stop for a bite at the local diner in Townsend center, or an ice cream.
0.8 miles of this trail now consists of crushed gravel
There's another couple of miles of mostly paved trail that goes beyond the parking lot in Lebanon. That's an excellent section of the trail. It took us all the way to Glen Road in West Lebanon.
I started in Acton and went up to Chelmsford. Plenty of parking and clean bathrooms—bonus! I really enjoyed this trail and look forward to doing the southern half soon.
I parked at the Delta Dental stadium and proceeded south in this trail. I was alone. I saw some unhoused people’s tents by the water. At first I felt fine, I saw another woman walking her dog, but there wee very few people on the path. The a person passed me on a bike and then circled back to me, following me. I felt unsafe. I wanted to keep going, but it was clear to me this person would following me. I had to quickly retreat to my car. I don’t usually feel vulnerable, and I was terrified. Later I told a local friend about my experience and she told me that recently a person had abandoned their baby on this trail, aka it’s not a safe place to walk by yourself, especially as a wow man.
I'd ridden this trail a couple years ago, doing it in small sections, and had found it to be a nice ride with a decent surface, quite reasonable for my older hybrid. I only did about 6 miles today, from Keene southward before turning back, and those couple of detours noted in another review are still in place - taking you out onto the road for short stretches likely to avoid power line work being done.
I parked on 4th street and headed up stream. Met one dog walker along this stretch. The calm river views were peaceful and the trail mostly wide gravel. Crossing over Whittier St the trail becomes narrower with a challenging set of turns to go under RTE 16. The river becomes more lively and there is a nice view of rapids. The trail widens with more gravel when you reach the parking lot on Watson Road. I met several more dog walkers along this stretch
Other reviews are fair. Lots of starts and stops for a shorter trail, but also some nice lengths and well maintained. Being from the area, I knew what to expect. I had more fun dodging and beeping my horn at bunnies on my night ride, than I did going around children on my day ride. Nice either way.
It’s spring on the Rockingham and everything is in bloom! Lots is rocks blooming in the trail as well, so be careful. The horses have really chewed up the surface just past Chiver’s Pond towards Manchester - really lumpy and washboarded. It makes for some uncomfortable bicycling. All in all still a very pretty trail with lots to see along the way.
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