Find the top rated walking trails in Wolfeboro, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.




















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 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.
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.
Gorgeous walk. We made the mistake of bringing our bikes and missed the no bike sign. Woops. Lessons learned. Great walking path with kids and pups.
I'm used to riding on gravel and I have ridden sections of this trail many times so I know what to expect. This last winter and spring have been pretty hard on the trail. Obviously some knuckleheads on bikes and horses have been on the trail when its been wet and soft and in spots its chewed up. There is also a need for some more driveway pack in sections as the larger stones that underlay the wear surface are poking through. The culvert under Hooksett Road is washed out and very rough, some drainage work needs to be done at this location. Not sure who is actually responsible for maintenance.
This is one of my favorite Trails for rollerblading and skating the only thing be careful Crossing in certain places make sure to watch the cars.
Our family loves this trail for it's wide, flat route that provides great views of the bay, connections to other trails like the Back Cove Trail and the Bayside Trail, and connections to the Old Port and Eastern Prom (beach, playground, greenspace, etc.).
Started on the Wakefield side off RT 16. I enjoyed the challenge of the rails still in place. Keeps it fun and challenging! Each crossing had a sign saying to walk your bike over the rails, not sure how so many people fall walking there bikes over the rails. The rails can be challenging when passing oncoming people. I’m not ranking the trail lower for this, but some people would only get a one ¿¿ review ¿ Bring a picnic and enjoy the state park!
Great ride! Plenty of parking at both ends. As noted in earlier reviews, it is not a rail trail, being hilly with some steep pitches. As an out-and-back it's over 1,500' in elevation gain (easier from north to south if you do it only one way).
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!!
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