Find the top rated horseback riding trails in Gray, 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.
We are on week 2 of a 2-week Northeast rail trail tour and we’re experienced cyclists. I should have believed the Trailguide when it warned that this one wasn’t well-suited for hybrid bikes. We only made it 6 miles out of Livermore Falls before turning around. There were only a few stretches of packed sand. The rest was loose sand or chunky rock. For reference, we were riding an Allied Alpha and a Cannondale Supersix Evo SE. Would have been a blast on a fatty.
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.
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.
First time on this trail and we loved it! We were on gravel grinder bikes, and the trail was perfect for this type of bike. We found the trails were in great condition. We did an out and back turn around at 6 miles. We will definitely return possibly for increased distance and more exploration on trails around Titcomb ski area.
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)
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