We parked at the Windham PO and rode along the tracks until we got to Rt-35, did a bit of exploring at the Otter Ponds, then came back. It was a sweet ride: no bugs, great Sharon weather—we were a little disappointed that we couldn’t go directly to the Lake, but I see now we could have gone left and gotten to the water…. Next time. We stopped at the Orchard Ridge Farm and had a delicious cider donut at the intersection with Sebago Lakes Rd. ~10

This trail is for mountain or hybrid bikes, definitely not road bikes.
Agree with others in that there are more pedestrians near Wolfboro but the trail gets much less traveled the farther away you go.
Also agree that the trails are narrow but this is not an issue because the visibility is so good. Most of the time, you can see people coming from other direction literally hundreds a feet ahead of time. I did get stuck behind a few slower bikers but was able to pass at one of the railroad track crossovers.
As the railroad track crossovers, you just have to slow down and ensure your front tire is crossing at a 90 degree angle. I didn’t have any issues at all but just be mindful, slow down and steer the front tire to cross over perpendicular to the rail.
So, definitely some things to consider and manage but well worth it in my opinion.

As many others have noted, this trail is not safe for bikes, especially road and hybrid models. We read the reviews warning us in advance and rode wide tire bikes. Despite rubber mats at many of the points where you transition from between the rails to beside them or vice versa, it's still possible to get a tire caught in the small gap between the mat and the rails and take a fall. Be forewarned to SLOW DOWN or walk your bike across these numerous transition points. Also, the sections of the trail that run between the rails are too narrow for a bike going one way to safely pass a walker going the other. When it's two bikes going in opposite directions, one has to come to a stop to pass safely. The sections of the trail outside the rails aren't much wider and the railroad ties extend about six inches beyond the rails, further squeezing the available space. My conclusion is that there must be hundreds of single bike, bike-bike and bike-pedestrian accidents annually.

The trail is otherwise quite nice. Its almost totally flat and there's plenty of shade.

This is a very scenic path traveling through woods most of the time, along marshes, hidden ponds and across Lake Wentworth. But this path has railroad tracks along the whole path, which makes the trail narrow in most places. BUT - be warned -
this trail will not be as enjoyable for some. Others will be fine with the challenges.
1. Learn how to travel safely across steel rails, since you will have to do this at least two dozen times, often within a tight narrow space. If you do not cross as close to 90 degrees to the rail, you risk you bike tire slipping out from under you. How do you I know? There are some short videos on You Tube that address this.
2. From the Wakefield end, park at the lot near the Miss Wakefield diner, so you don't have to cross Route 16, a very busy road.
3. The closer you get to Wolfboro, there are more pedestrians, and some think their right of way is the whole path, not half. I would end the trip at route 109A where the railcar rides are located, unless you really want to go to Wolfboro.
4. I found passing others on the trail that were coming the other way could be stressful, since there is little room to move over. One or both of you will have a hard rail on one side of you and if not, then the edge of the path often dropped off.
5. At the beginning of the trail at Route 16 you do have a couple of short steep ups and downs. Otherwise the trail is fairly flat.

Okay - nice trail - very pretty BUT my issue is the sections where they laid the trail in between the still existing train tracks - clever idea to save money??? BUT it makes it very narrow and when passing walkers and other bikers it gets a little hairy (in fact our side mirror was clipped by a biker going in the opposite direction that's how narrow it is) .... try not to go at a busy time and be prepared for tight squeezes on those sections where the trail is between the tracks ---- ALSO I would NOT recommend this for recumbents or other wide bikes - it just isn't safe for those kinds of cycles - otherwise like i said nice scenery but be forewarned

Great ride, passed a few people on the narrow section of the trail, but had no problems passing each other. I rode the trail after a heavy 2 days of rain, so it was wet, lots of mud, large puddles of rain, it got a little dirty! LOL

Ran the length of the trail to set up a Fastest Known Time segment. Was surprised by how beautiful the whole trail was, and how much the flora changed throughout. Id like to go back at a slower pace and stop at some of the towns it crosses (like Raymond and Epping)

Didnt realize there was a rail trail that ran through Rochester/Farmington, and came upon it by accident. Rochester side has more parking, and a few short side trails in a nice little park. The trail is a mix of gravel, dirt, sand. Had no issues running the length of it.

Finally did what I wanted to do for years. Biked from Northfield using the Lake Winnipesaukee trail to the Northern Rail Trail to the Fireside Inn in Lebanon NH. This was a weekend bike trip I wanted to do for a long time and had the perfect weather. My suggestion if you are going north and want to connect to the Northern Rail Trail instead of back tracking I would take Chance Pond Road. Once you go up the road a little cut to the right before the bridge going across the road. That bridge is part of the Northern Rail Trail. The hill to get to the bridge is quite steep so I recommend to walk the bike. Once on the bridge free sailing. My half way mark was the Danbury Country Store. They are very friendly to bikers and if you have an ebike they have a charging port on the right hand side of the store. Also have a deck on the front of the store with tables and chairs where you can have a meal while the bike is charging. Deli inside to grab something to eat.

Will say the more north you go the rougher the trail becomes. Some spots is an overkill of gravel that is very loose. Not very safe where you are trying to keep your balance and difficult to get any speed. Other than that a lot of lakes and scenery along the way. If you are using Google Maps along the trip it will suggest to get off the trail for 2 miles and get back on the trail. I recommend to stay on the trail. The fireside inn in Lebanon was about 1.5 miles off the trail and the hotel is bike friendly. You are in walking distance of a Walgreens and restaurants near by. Also there is free breakfast in the morning. A lot of off ramps along the trail for eatery which I believe was set up for snowmobiles in the winter time but if your bike has good suspension they are usable for bikers also. If you are using an ebike like I was the trip is durable as long as you save your power on the inclines and heavy gravel spots. The Danbury Country Store is ideal for charging as you take a break.

There is one spot on the trail you want to be careful on. On the way back past Enfield there is a steep incline with a pond to the right of you. To your left is a metal frame for a bridge and the trail is very narrow and a blind turn to the left. If someone was coming my way it would of been a major accident. I can't stress enough to be careful there.

Overall a fun bike trip if you are up for the challenge. I could of done each day trip within 5 to 6 hours but decided to take my time and do a lot of stops along the way and take pictures. I recommend to do the same.