Find the top rated running trails in Winthrop, whether you're looking for an easy short running trail or a long running trail, you'll find what you're looking for. Click on a running trail below to find trail descriptions, trail maps, photos, and reviews.
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)
Back Cove Trail is short, but sweet. The hard packed dirt is perfect for a jog, walk, or quick bike ride.
I started at 8:00 on an exceptionally still, brisk, mid October Sunday morning. The water was like glass and provided a perfect reflection of the downtown Portland skyline.
Other photo ops of the cove, wildlife, and beautiful classic homes were revealed to me as I made my way around the loop.
At only 3.6 miles, be sure to combine this with the also interesting Eastern Promenade Bike Trail for a total of nearly 8 miles between the two.
(Don't bother including the Bayside Trail which also connects to Back Cove and Promenade. It doesn't go by a bay and is about as appealing as riding down an alley)
This is a pretty and easy trail, but it is in real need of mainternance. The trail is in good shape from the South Windham start through the Gambo Road playing fields/parking. Once you cross over the river, the trail gets progressively worse. The biggest downfall is the amount of potholes' but there are also quite a few areas that are collapsing/leaning.
I am handicapped and ride a recumbent trike, so my perspective is a bit different than that of a mountain biker; but it would be nice if the DOT, or Gorham & Windham, put some money into maintaining the trail.
Was a wonderful morning for a bike ride,
We started in Livermore Falls and loved it! However, about 6 miles north, the trail is washed out and collapsed into a ravine. We tried to go around out on Main Street and up Macomber, but Macomber St was also washed out about 1/2 way up the hill and the road was closed. Will have to go South from Farmington next time!
It's less than 4 miles one way. Nice trail but short
I love walking on the trails, I started walking there a year ago, its helped me to build my strength and lungs from struggling with long covid, its quiet and peaceful, but I'm afraid the allowing of atvs is going to ruin that, ill see how it goes but if the atvs ruin the peaceful surroundings ill be looking for another peaceful place.
Walked this trail for many years and they have fix it up nice
My family goes out to Shaw park often and get right on the trail. We can’t wait for the trail to extend past our house in Steep Falls!
Flat, quiet, road crossings are few over the first 8 miles and well lit/marked. No portapotties, which is unreasonable. Lovely ride thru forest and wetlands.
Lovely, flat, well kept. I started a bit further back at the Belfast Boathouse, walked all the way out and back for almost 6 miles.
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