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Explore the best rated trails in Westbrook, ME, whether you're looking for an easy walking trail or a bike trail like the Papermill Trail and Eastern Promenade Trail . With more than 25 trails covering 136 miles you're bound to find a perfect trail for you. Click on any 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)
Imagine having a country estate in the woods of Maine and being afforded the opportunity for long, leisurely strolls down your own private lane. That's the feel of the Eastern Trail experience from Biddeford to Kennebunk.
I did it on a bike rather than on foot, but most of the friendly locals I encountered were walking or jogging to take advantage of the ideal weather and perfectly flat, smooth trail for a mid October afternoon outing.
Because of the natural trail surface and the spectacular fall color, I chose to take it nice and slow in order to savor my time there. I can't imagine doing this trail any other way since I found myself carefully peering into the woods on both sides taking in the sights.
My memories of this trail are of simplicity and peacefulness: a beaver pond here, a small creek winding through the woods there, the crossing of the Kennebunk River, a single track muddy path up to Alewive Road in Kennebunk after crossing over busy Highway 95, conversing with friendly local bicyclists, and of course the wooden rail fences lining much of the leaf carpeted trail through the gloriously colored woodlands.
My wife and I love this trail. We ride trails throughout NE and in NY and PA. This one is right up there among the best. The first leg from the Sanbornville roundabout has some rough sections that can be easily avoided by starting at the next parking area. ( where there is a spotless rent-a potty). From there the trail is smooth dirt surface. It is one lane wide either along side of the old tracks or between. Although it doesn’t make for good side by side riding it gives the trail an intimate charming feel. It crosses inside and outside the tracks often which is easy and makes it more interesting. The views constantly amaze and a f
One of the most beautiful rail trails in NH. In the fall it is breathtaking. It is quite narrow though, so passing requires one to step off the trail. The trail crosses over the tracks every mile or two and there's been mats or planks placed there to make crossing easier with bike tires. However for the most part the mats have been worn down so much they're mostly useless. There are also many spots where the chip and sand have eroded away so dismounting is necessary.
My brother and I are experienced cyclists who rode this trail on our e-bikes twice this summer, with different experiences. Our first ride in June was a warm day after a warm night, and we had no problem riding across rails (on rubber mats) to ride from one side of the rails to the other side, or between the rails, as the metal rails were dry. Our second ride in October was on a warm day after a cold night where the temperature dropped below the dew point and water condensed on the rails. Though the air temperature warmed up, the rails (in the shady woods) remained cold and so continued to be wet and slippery. My tire slipped and I went down once before I realized that water was not evaporating off the rails except where rails were in direct sunlight. Fortunately I only suffered a skinned knee. After that I made all transitions with one foot off the pedal. My 1 5/8 inch tires were OK for the ride, but I would never ride my skinny-tire road bike here. I will return because this is a unique trail in beautiful surroundings, and the 25 mile round trip from Wakefield (with lunch on Lake Winnipesaukee in Wolfeboro) is a beautiful day trip from Southern Maine.
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,
It's less than 4 miles one way. Nice trail but short
This is a beautiful trail, but dangerous. Besides the narrow trail and track crossings- slow down and ride over at a 90 degree angle- there are ridges down some of the hills, and steep banks along the side. You have to pay attention 100%. 2 of us fell and really hurt ourselves. Wolfeboro is a great destination, though!
Not for bikes. Such a shame .it would be a great asset to the community.
What a great morning to ride along this beautiful trail! It is a tight squeeze with oncoming bikes since it’s only as wide as the train tracks. Nevertheless,I’d definitely recommend it!
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