Headed east 10 miles from Lake Massebesic. Trail surface was rutted and very bumpy. Frequent large rocks sticking up and some wet/muddy areas. Not pleasant riding on a touring bike with 32mm tires. A fat bike or full suspension mountain bike would be a better choice. Four long culvert underpasses were too low to walk upright. Generally not much fun. I rode back mostly on parallel roads (which were very nice).

Parked at the Windham Post office and followed the train tracks about 5 miles. Paved trail follows the tracks on the segment I rode on. Part of the trail was still blocked by snow and impassable by bike. Looking forward to riding much further when the snow is gone! Trail goes through woods, past farms and fields and leads to a dam. There’s a small farm called Orchard Ridge along the trail to get drinks and snacks. Lots of quiet neighborhoods to ride around in as well.

goes by some lakes and marsh areas. Different as it goes on and off between rails filled with sand and gravel. beautiful spot at the end with lake winnepasaki.

The trail has been extended 0.4 miles south of Fisher Street, though there is no obvious parking at that end. Start near the south end, so you can partially coast on the return.

This is a difficult trail to assign a star rating to as parts of it are great and parts are not. It’s listed as a 29 mile trail but in reality it is split into 5 sections with 2 sections being on busy roads. I’ll break it down by section starting at the southern end in Kennebunk. I. 6-mile off-road section from Kennebunk to Biddeford - 5 stars. This is a great section featuring a well-maintained hard packed dirt trail through the woods. II. 5 mile on-road section through Biddeford and Saco - 2 stars. The first couple of miles are okay as you can ride on a sidewalk and residential streets. If you just do the first couple of miles combined with the first 6 mile off road section, it’s a nice 16 mile round trip. The issue is the next 2.5 miles is on busy roads through the congested areas of Biddeford and Saco. III. 7 mile off-road section from Saco to Scarborough - 5 stars. I’ve been on dozens of trails throughout the Northeast and this is one of my favorites. The trail is hard packed and is in great condition and features a stretch through the scenic Scarborough marsh. IV. 4 mile on-road section from Scarborough to South Portland - 1 star. The first half mile is fine as it’s on a lightly traveled road. But after that, it’s 3+ miles on busy roads that are narrow in spots. I’ve only been on the stretch once and several times a car came with a couple of feet of me - no interest in doing this section again. V. 6 mile off-road section in South Portland - 3 stars. It’s certainly better than riding the streets of Portland or South Portland. But there’s just nothing special about - nothing too scenic until you hit the very end, the trail is in decent, not great, shape, and it’s not well marked. But the biggest negative is the number of times the path crosses busy streets - I’ve never been on another trail with so many busy street crossings over a short stretch. So, the star rating of the trail depends on what you are looking for. If you’re looking to do a round trip of around 15 miles or less, there are two sections that are great - Kennebunk to Biddeford and Saco to Scarborough. If you’re looking to do more than that, you’ll have to deal with at least a few miles of busy streets.

We rode the trail during the first week of October. The colors were spectacular, especially after about mile 6 in the bog areas. There is wonderful variety along the trail as one starts out in Wolfeboro, goes on causeways through Lake Wentworth, through Wentworth State Park and then on through woods and bogs.

The trail itself requires riders to pay lots of attention to safety. Much of the trail is situated between the two metal rails of the old train track--so it is quite narrow. This is rideable, though. As others have mentioned, there are many points where you switch onto a hard packed limestone trail next to the tracks. It's turning off the rails onto the limestone trails where one must slow down and do a sharp turn. We encountered 2 people who had fallen at these turn off points and one accomplished rider in our group fell as well. It's just easy to catch your tires in the crack between the rails if you don't do almost a 90 degree turn.

All that said, it's a rustic and beautiful ride and I'd highly recommend it for hybrid or gravel bikes. And, there's amazing ice cream at the iconic Bailey's Bubble when you get back to Wolfeboro!

My wife and rode 10 miles through Biddeford to the Scarborough Marsh and back. We felt the town part was pretty well marked but you need to pay attention as you transition from sidewalks, to streets, to crosswalks, etc. Once you navigate that part of the trail it lines out straight north to the marsh. This section is a very pleasant and wide part with several road crossings. The roads aren't especially busy and gives access to businesses and a change in route if desired. Even if the town section isn't the most desirable it is nice to be able to jump on a trail right in town. Well worth the effort to ride this section of trail.

My wife and I rode this trail for a few miles out of Wolfeboro. The builders of this trail did a wonderful job navigating through town. As you leave town you get lovely views of the lake especially when riding on the causeway (I will call it). We found no trouble navigating over the rails. There seemed to be plenty of room to meet other bikers and walkers. This whole area is really fantastic.

I’ve ridden Kennebunk to Biddeford a couple of times in the past week (late Sept), the trail is well maintained and marked. The few vehicle crossings have cross walks and signage for drivers. This is a beautiful trail that I would highly recommend, looking forward to riding all the way to South Portland!