Conway, NH Mountain Biking Trails and Maps

354 Reviews

Looking for the best Mountain Biking trails around Conway?

Find the top rated mountain biking trails in Conway, whether you're looking for an easy short mountain biking trail or a long mountain biking trail, you'll find what you're looking for. Click on a mountain biking trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
20 Results
Activities
Length
Surfaces
Type

Ammonoosuc Rail Trail

19.2 mi
State: NH
Ballast, Dirt, Gravel, Sand

Bethel Pathway

1.7 mi
State: ME
Asphalt, Crushed Stone, Dirt, Grass

Black Pond Trail

0.8 mi
State: NH
Dirt

Blackmount Rail Trail

5 mi
State: NH
Cinder, Gravel, Woodchips

Conway Branch

21 mi
State: NH
Ballast, Gravel

Cross Vermont Trail (Montpelier & Wells River Trail)

22.9 mi
State: VT
Ballast, Dirt, Gravel, Sand

Farmington Recreational Rail-Trail

6 mi
State: NH
Ballast, Cinder, Dirt, Gravel, Sand

Guinea Pond and Flat Mountain Trails

11.5 mi
State: NH
Ballast, Dirt, Grass

Lincoln Woods Trail

2.7 mi
State: NH
Ballast

Nanamocomuck Trail

12 mi
State: NH
Ballast

Northern Rail Trail

57.6 mi
State: NH
Cinder, Crushed Stone

Presidential Rail Trail

18 mi
State: NH
Crushed Stone, Grass, Gravel

Riverton Rail Trail

1.5 mi
State: ME
Concrete, Dirt, Sand

Rob Brook Trail

2 mi
State: NH
Dirt, Gravel

Sanford-Springvale Rail Trail

5.9 mi
State: ME
Gravel

Sawyer River Trail / Sawyer River Road

7.5 mi
State: NH
Ballast, Dirt, Grass, Sand

West Milan Trail

4.5 mi
State: NH
Gravel

Wild River Trail

15 mi
State: NH
Dirt, Gravel

York Pond Trail

6.5 mi
State: NH
Dirt
Trail Image Trail Name States Length Surface Rating
The Ammonoosuc Rail Trail carries its users for 19.2 miles along the scenic river that shares its name and is itself a destination for fishing, kayaking, and canoeing. The trail passes through a...
NH 19.2 mi Ballast, Dirt, Gravel, Sand
The Bethel Pathway is a bucolic pathway open for walking, mountain biking, walking dogs and in the winter, snowshoeing and cross-country skiing. The trail begins on Sunset Road as a crushed stone...
ME 1.7 mi Asphalt, Crushed Stone, Dirt, Grass
The Black Pond Trail itself is short but it can be linked with other trails that run through the forest in the White Mountains of New Hampshire, just northeast of Lincoln. Specifically, the Black Pond...
NH 0.8 mi Dirt
In Woodsville the trail starts across from the Subway Restaurant across from the the Oceans Job Lot Store and next to the Woodsville Machine Shop and YES Yankee Electrical Supply up and down a short...
NH 5 mi Cinder, Gravel, Woodchips
The Conway Branch trail runs for 21 miles along an old rail corridor between State Route 113 in Conway and Polly's Crossing in Ossipee. The trail is popular with snowmobiles and rail car clubs; the...
NH 21 mi Ballast, Gravel
Locals lovingly describe the Cross Vermont Trail as a patchwork quilt that will ultimately form a 90-mile trail from Lake Champlain in the west to the Connecticut River in the east. A component of the...
VT 22.9 mi Ballast, Dirt, Gravel, Sand
The Farmington Recreational Rail-Trail runs for 6 miles between the towns of Rochester and Farmington. The trail parallels the Cocheco River and State Route 11 through a wooded corridor. The trail is...
NH 6 mi Ballast, Cinder, Dirt, Gravel, Sand
These connecting trails follow the bed of the old Beebe River Railroad up to Flat Mountain Pond, a large, remote pool high in the Sandwich Range Wilderness. This is a great trip for advanced mountain...
NH 11.5 mi Ballast, Dirt, Grass
The Lincoln Woods Trail runs for 2.6 miles along the east branch of the Pemigewasset River. You can combine the trail with other trails that run through the forest in the White Mountains of New...
NH 2.7 mi Ballast
The Upper and Lower Nanamocomuck Trails in White Mountain National Forest are accessible from Kancamagus Highway (SR 112) west of Conway. The trails are open for hiking in summer and cross-country...
NH 12 mi Ballast
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. It weaves through Grafton and Merrimack counties and is less than a 2-hour drive...
NH 57.6 mi Cinder, Crushed Stone
Located in the scenic Presidential Range in the White Mountains, the Presidential Rail Trail is a scenic and pleasant route, providing an alternative view of Mount Washington and the surrounding area....
NH 18 mi Crushed Stone, Grass, Gravel
The scenic Riverton Rail Trail—also known as “Sandy Road” by residents of Portland’s Riverton neighborhood—follows the former corridor of the Portland-Lewiston Interurban Railroad, which stopped...
ME 1.5 mi Concrete, Dirt, Sand
The Rob Brook Trail is mostly flat, following the bottomlands of its namesake creek through the White Mountains National Forest. The trail is open to mountain biking and hiking, with cross-country...
NH 2 mi Dirt, Gravel
The Sanford-Springvale Rail Trail (also known as Railroad Trail) traverses the woods on either side of Sanford’s scenic Springvale community in southern Maine. Founded by a mill owner in the 17th...
ME 5.9 mi Gravel
The Sawyer River Trail/Sawyer River Road lies deep in the forested heart of the 1,200-square-mile White Mountain National Forest. The 7.5-mile route traces an old logging railroad that’s now part...
NH 7.5 mi Ballast, Dirt, Grass, Sand
Many rail-trails start at a vintage depot, an old caboose, or a rusty locomotive acquired by the local historical society. The Warren to East Haverhill Railroad Grade Trail, however, starts at the...
NH 10.8 mi Dirt
The West Milan Trail follows a portion of the Upper Ammonoosuc River along State Route 110 northwest of Berlin. The mult-use trail is relatively flat and follows a scenic mountain valley...
NH 4.5 mi Gravel
Most of the Wild River Trail falls within the Wild River Wilderness and is off-limits to bikes. At it's southern end, the trail meets the Wildcat River Trail, near Bog Brook. From here, you can bike...
NH 15 mi Dirt, Gravel
The York Pond Trail begins at the Berlin Fish Hatchery (just past the locked gate), going through a notch in the Mountains to the south and west to Bunnell Brook. The trail leads to Willard Notch,...
NH 6.5 mi Dirt

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Trails by activity

Northern Rail Trail

NH - 57.6 miles

Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. It weaves through Grafton and Merrimack counties and is less than a 2-hour drive...

Riverton Rail Trail

ME - 1.5 miles

The scenic Riverton Rail Trail—also known as “Sandy Road” by residents of Portland’s Riverton neighborhood—follows the former corridor of the Portland-Lewiston Interurban Railroad, which stopped...

Blackmount Rail Trail

NH - 5 miles

In Woodsville the trail starts across from the Subway Restaurant across from the the Oceans Job Lot Store and next to the Woodsville Machine Shop and YES Yankee Electrical Supply up and down a short...

Riverton Rail Trail

ME - 1.5 miles

The scenic Riverton Rail Trail—also known as “Sandy Road” by residents of Portland’s Riverton neighborhood—follows the former corridor of the Portland-Lewiston Interurban Railroad, which stopped...

Presidential Rail Trail

NH - 18 miles

Located in the scenic Presidential Range in the White Mountains, the Presidential Rail Trail is a scenic and pleasant route, providing an alternative view of Mount Washington and the surrounding area....

Sawyer River Trail / Sawyer River Road

NH - 7.5 miles

The Sawyer River Trail/Sawyer River Road lies deep in the forested heart of the 1,200-square-mile White Mountain National Forest. The 7.5-mile route traces an old logging railroad that’s now part...

Guinea Pond and Flat Mountain Trails

NH - 11.5 miles

These connecting trails follow the bed of the old Beebe River Railroad up to Flat Mountain Pond, a large, remote pool high in the Sandwich Range Wilderness. This is a great trip for advanced mountain...

Accordion

Sanford-Springvale Rail Trail

ME - 5.9 miles

The Sanford-Springvale Rail Trail (also known as Railroad Trail) traverses the woods on either side of Sanford’s scenic Springvale community in southern Maine. Founded by a mill owner in the 17th...

Conway Branch

NH - 21 miles

The Conway Branch trail runs for 21 miles along an old rail corridor between State Route 113 in Conway and Polly's Crossing in Ossipee. The trail is popular with snowmobiles and rail car clubs; the...

Bethel Pathway

ME - 1.7 miles

The Bethel Pathway is a bucolic pathway open for walking, mountain biking, walking dogs and in the winter, snowshoeing and cross-country skiing. The trail begins on Sunset Road as a crushed stone...

York Pond Trail

NH - 6.5 miles

The York Pond Trail begins at the Berlin Fish Hatchery (just past the locked gate), going through a notch in the Mountains to the south and west to Bunnell Brook. The trail leads to Willard Notch,...

West Milan Trail

NH - 4.5 miles

The West Milan Trail follows a portion of the Upper Ammonoosuc River along State Route 110 northwest of Berlin. The mult-use trail is relatively flat and follows a scenic mountain valley...

Warren to East Haverhill Railroad Grade Trail

NH - 10.8 miles

Many rail-trails start at a vintage depot, an old caboose, or a rusty locomotive acquired by the local historical society. The Warren to East Haverhill Railroad Grade Trail, however, starts at the...

Lincoln Woods Trail

NH - 2.7 miles

The Lincoln Woods Trail runs for 2.6 miles along the east branch of the Pemigewasset River. You can combine the trail with other trails that run through the forest in the White Mountains of New...

Ammonoosuc Rail Trail

NH - 19.2 miles

The Ammonoosuc Rail Trail carries its users for 19.2 miles along the scenic river that shares its name and is itself a destination for fishing, kayaking, and canoeing. The trail passes through a...

Farmington Recreational Rail-Trail

NH - 6 miles

The Farmington Recreational Rail-Trail runs for 6 miles between the towns of Rochester and Farmington. The trail parallels the Cocheco River and State Route 11 through a wooded corridor. The trail is...

Wild River Trail

NH - 15 miles

Most of the Wild River Trail falls within the Wild River Wilderness and is off-limits to bikes. At it's southern end, the trail meets the Wildcat River Trail, near Bog Brook. From here, you can bike...

Northern Rail Trail

NH - 57.6 miles

Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. It weaves through Grafton and Merrimack counties and is less than a 2-hour drive...

Nanamocomuck Trail

NH - 12 miles

The Upper and Lower Nanamocomuck Trails in White Mountain National Forest are accessible from Kancamagus Highway (SR 112) west of Conway. The trails are open for hiking in summer and cross-country...

Cross Vermont Trail (Montpelier & Wells River Trail)

VT - 22.9 miles

Locals lovingly describe the Cross Vermont Trail as a patchwork quilt that will ultimately form a 90-mile trail from Lake Champlain in the west to the Connecticut River in the east. A component of the...

Black Pond Trail

NH - 0.8 miles

The Black Pond Trail itself is short but it can be linked with other trails that run through the forest in the White Mountains of New Hampshire, just northeast of Lincoln. Specifically, the Black Pond...

Rob Brook Trail

NH - 2 miles

The Rob Brook Trail is mostly flat, following the bottomlands of its namesake creek through the White Mountains National Forest. The trail is open to mountain biking and hiking, with cross-country...

Blackmount Rail Trail

NH - 5 miles

In Woodsville the trail starts across from the Subway Restaurant across from the the Oceans Job Lot Store and next to the Woodsville Machine Shop and YES Yankee Electrical Supply up and down a short...

Sanford-Springvale Rail Trail

ME - 5.9 miles

The Sanford-Springvale Rail Trail (also known as Railroad Trail) traverses the woods on either side of Sanford’s scenic Springvale community in southern Maine. Founded by a mill owner in the 17th...

Blackmount Rail Trail

NH - 5 miles

In Woodsville the trail starts across from the Subway Restaurant across from the the Oceans Job Lot Store and next to the Woodsville Machine Shop and YES Yankee Electrical Supply up and down a short...

Bethel Pathway

ME - 1.7 miles

The Bethel Pathway is a bucolic pathway open for walking, mountain biking, walking dogs and in the winter, snowshoeing and cross-country skiing. The trail begins on Sunset Road as a crushed stone...

Presidential Rail Trail

NH - 18 miles

Located in the scenic Presidential Range in the White Mountains, the Presidential Rail Trail is a scenic and pleasant route, providing an alternative view of Mount Washington and the surrounding area....

Accordion

York Pond Trail

NH - 6.5 miles

The York Pond Trail begins at the Berlin Fish Hatchery (just past the locked gate), going through a notch in the Mountains to the south and west to Bunnell Brook. The trail leads to Willard Notch,...

Wild River Trail

NH - 15 miles

Most of the Wild River Trail falls within the Wild River Wilderness and is off-limits to bikes. At it's southern end, the trail meets the Wildcat River Trail, near Bog Brook. From here, you can bike...

Ammonoosuc Rail Trail

NH - 19.2 miles

The Ammonoosuc Rail Trail carries its users for 19.2 miles along the scenic river that shares its name and is itself a destination for fishing, kayaking, and canoeing. The trail passes through a...

Lincoln Woods Trail

NH - 2.7 miles

The Lincoln Woods Trail runs for 2.6 miles along the east branch of the Pemigewasset River. You can combine the trail with other trails that run through the forest in the White Mountains of New...

West Milan Trail

NH - 4.5 miles

The West Milan Trail follows a portion of the Upper Ammonoosuc River along State Route 110 northwest of Berlin. The mult-use trail is relatively flat and follows a scenic mountain valley...

Warren to East Haverhill Railroad Grade Trail

NH - 10.8 miles

Many rail-trails start at a vintage depot, an old caboose, or a rusty locomotive acquired by the local historical society. The Warren to East Haverhill Railroad Grade Trail, however, starts at the...

Guinea Pond and Flat Mountain Trails

NH - 11.5 miles

These connecting trails follow the bed of the old Beebe River Railroad up to Flat Mountain Pond, a large, remote pool high in the Sandwich Range Wilderness. This is a great trip for advanced mountain...

Black Pond Trail

NH - 0.8 miles

The Black Pond Trail itself is short but it can be linked with other trails that run through the forest in the White Mountains of New Hampshire, just northeast of Lincoln. Specifically, the Black Pond...

Northern Rail Trail

NH - 57.6 miles

Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. It weaves through Grafton and Merrimack counties and is less than a 2-hour drive...

Riverton Rail Trail

ME - 1.5 miles

The scenic Riverton Rail Trail—also known as “Sandy Road” by residents of Portland’s Riverton neighborhood—follows the former corridor of the Portland-Lewiston Interurban Railroad, which stopped...

Conway Branch

NH - 21 miles

The Conway Branch trail runs for 21 miles along an old rail corridor between State Route 113 in Conway and Polly's Crossing in Ossipee. The trail is popular with snowmobiles and rail car clubs; the...

Cross Vermont Trail (Montpelier & Wells River Trail)

VT - 22.9 miles

Locals lovingly describe the Cross Vermont Trail as a patchwork quilt that will ultimately form a 90-mile trail from Lake Champlain in the west to the Connecticut River in the east. A component of the...

Nanamocomuck Trail

NH - 12 miles

The Upper and Lower Nanamocomuck Trails in White Mountain National Forest are accessible from Kancamagus Highway (SR 112) west of Conway. The trails are open for hiking in summer and cross-country...

Sawyer River Trail / Sawyer River Road

NH - 7.5 miles

The Sawyer River Trail/Sawyer River Road lies deep in the forested heart of the 1,200-square-mile White Mountain National Forest. The 7.5-mile route traces an old logging railroad that’s now part...

Rob Brook Trail

NH - 2 miles

The Rob Brook Trail is mostly flat, following the bottomlands of its namesake creek through the White Mountains National Forest. The trail is open to mountain biking and hiking, with cross-country...

Farmington Recreational Rail-Trail

NH - 6 miles

The Farmington Recreational Rail-Trail runs for 6 miles between the towns of Rochester and Farmington. The trail parallels the Cocheco River and State Route 11 through a wooded corridor. The trail is...

Recent Trail Reviews

Eastern Trail

Great trail with some not so great sections

October, 2021 by potterdunn

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.

Cotton Valley Rail-Trail

Takes some maneuvering--but a lovely ride

October, 2021 by creischl

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!

Eastern Trail

Lots of really nice parts

October, 2021 by mgundy.xo

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.

Accordion

Cotton Valley Rail-Trail

A fun and beautiful ride

October, 2021 by mgundy.xo

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.

Eastern Trail

Kennebunk 2 Biddeford

September, 2021 by nap789

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!

Winnipesaukee River Trail

decent trail

September, 2021 by johncneal10

Not bad. Started in Franklin. Tilton not that bad. Need to use street for a bit, stay on north side of Rt 3 in sidewalk. Ends at a McDonalds and Super 8 ( not motel 6). Good ride, too short

Franconia Notch Recreation Path

An Amazing Trail

September, 2021 by arooks78

What a great trail! I agree with one of the other reviews. That the trail is mostly uphill if you start from the Flume; coming back the other way is exhilarating! A couple of tough uphills, but they are short. The views are amazing. One tip: you can get going very fast downhill, but the trail is a bit bumpy so watch your speed, particularly if the trail is wet.

Presidential Rail Trail

Rough for the first 8 miles...

September, 2021 by bill.mason7680

I started at the western trailhead. The surface for the first four miles is large diameter crushed stone. The same stone used in the trailhead parking lot. It's not the kind of crushed stone you put on a multi use recreation trail. The next four miles was basically rough single track. I rode my gravel bike based on the (lackluster) description above. I jumped off at 8 miles and returned to my car on back roads. The crushed stone listed on the surface description is very misleading. This would be fine with a mountain bike. Front suspension would be best.

Mountain Division Trail

Beautiful day for an easy ride

September, 2021 by nikoniko

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

Cotton Valley Rail-Trail

Fun ride in the woods!

August, 2021 by demcvane

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.

Cotton Valley Rail-Trail

Another Vote for "Not Safe for Bikes"....and We Biked It

August, 2021 by tribe_fan

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.

Cotton Valley Rail-Trail

Know how to cross railroad rails safely

August, 2021 by nphillips_tl

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.

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