Find the top rated horseback riding trails in Pittsfield, 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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We rode the trail in early September on a Thursday and Friday. Thursday we started at Webster Lake and headed south (east?). Friday we rode from Webster Lake to the covered bridge. This second part of the trail was better riding than the other direction, which had more sand and was sometimes a slight bit challenging on our hybrid bikes (but maybe a better work out). We saw riders and walkers, but it was not crowded at all. Mostly we had this beautiful place to ourselves. We'll return for sure. (We camped at Granite State Campground about 30 min from where we began our rides.)
Really nice accessible trail for people of all abilities. Wheelchair friendly and just shy of all the requirements to be classified as a Universal Access Trail. Very well thought out trail, Bravo!!
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.
Beautiful trail. Enjoyed the sites, sounds and smells. It runs along the river. I got on at the Depot Rd parking lot in Boscawen. Very easy access and plenty of parking. I Road 15 miles. The trail is fairly level with very little incline.
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!
We went there today! What a super fast fun trail! Lots to see and do ! Bring a picnic lunch and spend the day!!!
Salem to Derry - entirely paved Awesome trail will do it again!
Started at Salem Depot and went north to Derry…awesome ride Entire path is pavement
Longest trail in State and is deservedly well rated by most. It is a consistently groomed crushed stone trail with few roots and rocks. Not many places to stop and sit which on a long ride can be helpful. Make sure to ride to the statue at the southern trail head.
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