Explore the best rated trails in Freeport, ME, whether you're looking for an easy walking trail or a bike trail like the Whistle Stop Rail-Trail and Eastern Promenade Trail . With more than 19 trails covering 97 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.
Really enjoyed our ebike ride to and from beginning to end and back. Easy parking right over the bridge from Mill apartments on the left! So well maintained, scenic and safe feeling for 2 seniors. Delicious pizza in Lisbon Falls.
So, the positives first. It's a well paved trail with views to a picturesque river.
However, forget the "ring your bell" or "on your left" helps. The proximity to Rt 1 (sometimes within 15 ft. or so) - and the associated traffic noise - all but end any communication, signals, or thoughts of a nice scenic contemplative ride. Also, parking at either end was sparse. And, yes, somewhat thankfully, it is short. A one and done.
We cycled 20 miles, starting at bug Light in South Portland to Scarborough. Mostly flat, asphalt surface. Some riding on bike path along street traffic but most riding is on the separate bike path along water and in green areas. Highly recommend for an easy ride.
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.
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)
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)
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