Explore the best rated trails in Waterboro, 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 45 trails covering 326 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)
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 had no problem riding this beautiful trail on e-bikes with 1 5/8 inch tires on a weekday in Sept. 2021 and again in August 2023. Both times we rode west from Newfield and noted that the trail has noticeably more rocks as we headed west of Raymond. We were glad we had front suspension forks. Dearborn Forest just past Onway Lake was our turnaround point at about 17 miles. At Route 125 (Main St.) in Epping, be sure to take the right trail at the fork to continue on the Portsmouth branch. The left trail is the Fremont Branch where you may find yourself riding with ATV's.
At Freetown Road (Route 102) in Raymond, McDonalds is just south of the trail. If you are looking for a tastier burger and have more time, go north one block on Route 102 to Route 27 (Hannaford on your right), then go left one block to Tuckaway Tavern & Butchery (featured on Guy Fieri's "Diners, Drive-Ins and Dives" television series).
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 wonderful trail. But I must add that I am very fond of many of the rail trails in New Hampshire. My wife and I are old and use E bikes with fat tires for our rail trail trips. However, on this trip we passed several riders using road bikes with skinny tires, and they were doing just fine.
From the start of the trip at Lake Massabesic to the end at Ash Swamp Road, this trail proved to be a most enjoyable trail with very few spots that required a little caution. Leaving Massabesic the trail is wide, hard packed and easy going. Mostly wooded areas with many brooks, swamps and for the most part, great scenery.
There were very few muddy or wet areas but all of them were easily navigated. But keep in mind, this trail crosses a few very busy highways. Luckily the first three busy roads you will encounter have tunnels, so you don’t have to cross the roads. Out of caution we got off our bikes and walked them through the tunnels, but a good rider might not have to do that.
As you make your way east there are some very interesting sites like the Emerson Mill site and a couple others that might spark later trips. The trail goes past several lakes and large rivers with very interesting spots to stop for a break or a snack. As you move east you will approach the Star Speedway, (a small racetrack) but is not open during the morning or early afternoon time periods. Further on you will have to cross a very busy route 125. Buy don’t worry, there is a traffic light on either side of the road and all you must do is press the button and wait for the light to stop all the cars, very fast and simple.
There is a rail museum and ice cream spot if you need a break or sugar fix right on the trail, so it makes a stop easy and quick. Continuing east you finally make it to the eastern end at Ash Swamp Road. There is an old rail station that is under restoration there with plenty of parking and easy access. All in all, this is a great trip that shouldn’t be missed.
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.
I'd thought maybe this trail wouldn't be suitable for my road bike w/ slightly wider tires, but it worked out fine. Surface was mostly hard packed dirt/gravel, at least the 9 miles I rode starting at the southern end in Newfields. There were some muddy spots and a few rocks and roots to avoid, but never had to get off the bike and walk. Ponds, swamps, brooks and lots of woods. A few easy road crossings, no road noise on this part. Well worth a ride.
Parked across from the Danbury County Store. Headed west towards Grafton. Only saw a coupe peopling using the trail this late Friday afternoon. Trail was smooth and dry even with rain the prior day.
The parking area on Depot Road in Raymond has plenty of room, even for a ride on a beautiful sunday. I rode east on my hybrid all the way to the starting point in Newfields with very little difficulty other than it turned into my longest rail trail ride to date, resulting in very tired legs over the last 5ish miles of the return trip. Only a couple of busy road crossings, one with a crossing signal, while all the rest of the crossings were just rural roads.
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