Find the top rated hiking trails in Kennebunk, whether you're looking for an easy short hiking trail or a long hiking trail, you'll find what you're looking for. Click on a hiking trail below to find trail descriptions, trail maps, photos, and reviews.
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.
Great trail to ride on, well maintained crushed stone path. We got on at mile 13.4 in Portsmouth and rode to mile 6.8 then turned around and headed back. A lot of tree coverage which is nice for shade but not much variation in scenery. Not sure if there is more to see further south on the trail. That being said, it’s still a great place to get outside and exercise!
Smooth cider trail all bikes, well signed, 3 road crossings well marked, full canopy not a lot to see except Hampton Airfield. Recommend stopping at Airfield after riding at restaurant and watch small planes.
Smooth level no hills, cider trail, good signage, full canopy. Recommend starting at South End near or at Hampton Airfield and at end of ride watch small planes and have lunch
We are bike-packing across the country with e-bikes. A good rail trail is such a nice escape from the road traffic - this one was a delight. Mostly solid packed surface, smooth, a few muddy spots. Very scenic with a mix of woods and wetlands. Watch your head on the tunnels. Highly recommend!
Rode this trail several times since mid-September. It is a nice length - 8 miles so not too long for a round trip. It is a new trail with all crushed stone, and it is a straight run and sufficiently wide. The scenery is typical woods. The trail crosses roads 2-3 times that are not too busy and all have lights. The parking lot, which is immediately south of the Airfield Café, is a decent size. The northern part of the trail ends by Route 1. Although I have not done it, you should be able to find your way into the city of Portsmouth from here using Islington St. or Middle Rd.
Did on e-bikes with 2" tires in early October. Done in 2-segments of 14 miles each (started in Newfields and then in Manchester and worked way to middle). From Manchester there are several lakes/ponds, so it is more scenic. Also, this segment has three railbed passes beneath the roads. You can stay on your bike for all but one - watch your head! Also the lead up and down to these tunnels is steep, so get some speed going up to them. From Newfield there are places to eat about 12 miles in. The trail is mostly crushed stone & some dirt.
Biked in October on e-bikes with 2" tires. From 33 Chestnut St (Dover). Went S (1 mile) and back then N (3 miles) and back. South is as much town as trail and is well paved. It also is tricky to find your way on the trail as it goes through the back of stores. We found someone to follow. The trip north is mostly dirt terrain and has many rocks and sewer caps. The trail varied from narrow to wide and had 2-spots where continuance was difficult to find, including spots by the bridge and a private drive (trail is on right of fence). You cannot maintain speeds over 12 mph on this part of the trail. Whereas, I didn't mind picking my way through the terrain, my wife hated it.
A real rail trail.¿ A little danger if you hit the rails.¿ You move from within, to the sides a lot. Worth the risk. Great scenery and condition. Biked with e-bike with 2.1" tires. Expect Wolfeboro to be crowded during summer and fall weekends. After the 12-mile ride to Wolfeboro, there are many wonderful places to stop for a bite to eat and drink. Of 20 Rail Trials we rode in October, this was one of the top two crushed stone trails we rode in NH.
We started in Manchester and rode east. The first 3 miles the surface was packed gravel with fall leaves but no rocks. We rode another 2 miles and found the path very bumpy with thicker gravel and rocks protruding. We have 2 inch tires but it wasn’t fun for us. We wanted to bike to Raymond but turned around. We have biked on other packed trails in NH without any issues but this path was worse after 3 miles.
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