Find the top rated horseback riding trails in Kennebunk, 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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Mixed feelings about this trail. I’m a new rider so more experience may make me rate higher in the future. The location is beautiful but the in and out of riding between the former rails can be stressful. You have to approach at proper angle or you will wipe out which I did just a mile shy of the end of the trail. Banged myself and my bike up pretty good. Pretty much impossible to pass along the trail. If someone is coming in the other direction better for one of you to pull off. I had to each time as I came close to hitting handlebars of passing bike a couple times. I would love to try it later in the fall but would be concerned if mats get covered by leaves.
Started at Oak Street trail head parking lot. Headed south, roughly 4 miles out and 4 back. Well maintained crushed packed stone. Best to turn back at Carpenters Bridge if bicycling without fat tires. Part after Carpenters Bridge is Sandy and moguls from ATV use.
We probably crossed the rails 15 times before my wheel caught and I went down, scraping my knee and hands, I got pretty bruised up. I couldn’t bend my knee to ride back and uber was not an option. So my husband rode back to the other end to get the car. This is dangerous and the trail is narrow for bikes and walkers at the same time. We had to stop so that bikes in the opposite direction could pass. Would be a nice ride if it were fixed up a bit.
Trail is nice and flat, some soft dirt (minimal), and small rocks across bridge. Trail needs a good chain drag, roots cut back, and rake. Otherwise it’s a good dirt trail with lots of shade. Excellent for walking dogs too!
Great views and we enjoyed the changes in grade and the turns, but a very short trail. Must be combined with Winni Trail, but that is also short.
Most of the trip is paved and runs through the town of Laconia. There appear to be homeless people (campers at least) on one portion of the trail. Short trail that must be combined with the WOW trail for a longer ride (still short).
Nice comfortable ride we started in the parking lot in North Hampton and came out on Borthwick Ave near the hospital 17 miles out and back route that will be pretty in the fall
Very poor it's not what it say you have barriers that you can't fit a trike through needs a lot of work Very little pavement on it.
Great trail. Bad culverts!!!
I bike rode Rockingham Rail Trail, Portsmouth branch for the first time today 6/29/25. Headed from Manchester east out 15 miles and back. Very nice trail, good base and I enjoyed the trail very much. HOWEVER, those underpass culverts 7-8 miles east of Manchester are DOWNRIGHT DANGEROUS!!!!! Very low clearance, terrible visibility, and a deteriorated and uneven riding platform all contribute to a recipe for a terrible accident and injury. I am a good rider, and I crashed today. I was barely creeping along and fortunately I was not seriously Injured. Something needs to be done to make these less dangerous. I do not know who is responsible for maintaining these underpass culverts, but please consider my concerns. I would volunteer to assist in improving these hazards. Reread the description and walking bikes in these culverts was recommended and I would agree. On site signage would be a good idea also. The trail gets 5 stars the culverts get 0 stars.
I enjoy the trail. I've seen cows bunnies and birds.
I've managed to ride portions of the trail between Fremont and Derry where it's open to summer OHRV on my hybrid bike (40mm gravel tires). It's not really pleasant as the trail is very sandy in sections to the point where I have had to walk my bike through sections. This is unfortunate because it's a great connector to the RT corridor that runs between Methuen, MA and Londonderry with the Rockingham Recreational trail from Manchester to Newfields. I get that summer OHRV use south of the North Woods is a scarce resource and that bikes do have the option of riding on the pavement. Except the shoulders of the roads are awful narrow. I could go on about the short sightedness of State and Local government but...
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