Find the top rated hiking trails in South Portland, 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.
Nice easy trail until it crosses the stream then turns into more challenging path. Small elevation changes. Lots of mosquitoes since it goes next to a stream/bog/swamp
So this trail has a hidden risk. Going from trail on the side of the rails to inside the rails can be tricky. My wife fell twice and skinned her knee pretty good. Also trail is narrow and has lots of walkers with dogs. Views are good near wolfboro but after that it’s a tree tunnel. Don’t need to do it again.
I rode the full trail starting in Wakefield at the Turntable park ( which had a good sized parking lot) to Wolfeboro and back. Smooth surface with packed gravel and stone dust. Watch yourself on the crossing when going over the rails so you don’t catch a wheel and go for a header. Good day of biking.
A lovely and fairly easy asphalt paved bike ride. I started in South Windham off Route 202 south of Rt 302. This app shows the parking at the Post Office but there is public parking south of the Post Office. There are signs on Rt 202 to show the Public Parking. Apparently, in 2023 the local Boy Scouts did some work to mark the parking and trail. Look for the little white signs “Sebago to the Sea Trail”. Park in the lot across from the Windham Fire Rescue South Station. Find the trail by looking at the Fire Station, look left and walk between the two buildings to a little grad & gravel trail. If you turn left, walk or ride behind the building about 100 yards to cross ice a 202 to the start of the asphalt path. If you turn right, the grass and gravel travel continues.
Tried riding this trail with a regular (skinny tire) bike. That's close to impossible. It's pretty obvious the trail has not been and is not maintained. It's rutted, has tree roots across it , has wet, muddy areas and worst of all, it has sections of very soft sand that make biking on it nearly impossible. It crosses NH Rte.11, a major two lane 55MPH highway, so be prepared. It is definitely not handicapped accessible. There are no facilities of any kind along or adjacent to the trail. Overall, a huge disappointment.
Nine riders went in. Only 4 came out without injury. Dangerous crossings over rails. Zigzag back and forth across tracks. Why not stay on just one side???? Needs maintenance to make it safer.
It is paved but it’s still very bumpy. Not ideal for rollerblades
We rollerbladed down this path, starting at the Maine State Visitor information center. It was smooth but very hilly. Also we tried to start in Standish but it was not paved.
Nice section starting from the Kennebunk elementary school parking lot. The trail switches to road riding in Biddeford turn left when the trail ends and you’ll see a Dunkin Donuts. Can you say coffee and pee
At only 2.1 miles, Eastern Promenade Trail packs a great deal of interest into its short length.
Starting near the Highway 295 bridge you'll be blessed with sensational views of the bay. Next, as you make your way past Fish Point, you'll be rewarded with the sight of massive cruise ships, vintage narrow gauge trains, and historic buildings.
What brought the greatest pleasure to me on this October Sunday morning bike ride were the throngs of people walking their dogs! It was like being at the National Dog Show! I had to stop at East End Beach which is essentially a dog park to watch the dogs happily play and cavort. This trail was most heavily populated with the dog walkers, joggers, and other pedestrians. We bicyclists were few and far between.
Be sure to combine this with the Back Cove Trail loop for nearly 8 miles of riding and get more bang for your buck!
(But do not bother combining it with another connecting trail - the Bayside Trail, which doesn't go along a bay and is about as appealing as riding down an alley)
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Scan the QR code to get TrailLink on your phone
Map Search
