Ossipee, NH Bike Trails and Maps

345 Reviews

Looking for the best Bike trails around Ossipee?

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

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Activities
Length
Surfaces
Type
18 Results
Activities
Length
Surfaces
Type

Back Cove Trail

3.6 mi
State: ME
Asphalt

Bayside Trail

1 mi
State: ME
Asphalt

Beth Condon Memorial Pathway

1.8 mi
State: ME
Asphalt

Cotton Valley Rail-Trail

12 mi
State: NH
Gravel

Dover Community Trail

3.8 mi
State: NH
Asphalt, Crushed Stone, Dirt

Eastern Promenade Trail

2.1 mi
State: ME
Asphalt

Eastern Trail

28.9 mi
State: ME
Asphalt, Crushed Stone, Sand

Fore River Parkway Trail

2.6 mi
State: ME
Asphalt

Franconia Notch Recreation Path

8.7 mi
State: NH
Asphalt

Lake Winnisquam Scenic Trail

1.8 mi
State: NH
Asphalt

Mountain Division Trail

9.7 mi
State: ME
Asphalt, Gravel

Northern Rail Trail

57.6 mi
State: NH
Cinder, Crushed Stone

Norway Branch Rail Trail

0.5 mi
State: ME
Crushed Stone

Riverton Rail Trail

1.5 mi
State: ME
Concrete, Dirt, Sand

Stevens Rail Trail

1.3 mi
State: NH
Dirt, Gravel

WOW Trail

2.7 mi
State: NH
Asphalt

West Foss Farm Trail

1.6 mi
State: NH
Dirt

Winnipesaukee River Trail

5.1 mi
State: NH
Asphalt, Crushed Stone, Dirt, Gravel
Trail Image Trail Name States Length Surface Rating
The paved Back Cove Trail rings its namesake tidal basin and offers lovely views of the Portland skyline. You also might spot great blue herons or other birds along the tree-lined waterfront. A...
ME 3.6 mi Asphalt
Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...
ME 1 mi Asphalt
The Beth Condon Memorial Pathway is located in the heart of Yarmouth, Maine. The path is named in honor of a high school student who was struck by a drunk driver while walking along US-1. The paved...
ME 1.8 mi Asphalt
The Cotton Valley Rail Trail connects the small town of Wakefield, near the Maine border, and the quintessentially quaint New England vacation town of Wolfeboro. In 2017 the towns held a...
NH 12 mi Gravel
The Dover Community Trail snakes its way through the heart of the Garrison City—so nicknamed for the fortified log houses, or garrisons, built by 17th-century settlers—-offering a variety of trail...
NH 3.8 mi Asphalt, Crushed Stone, Dirt
Old salts should love the Eastern Promenade Trail, as it skirts the shoreline of Portland’s Casco Bay and Portland Harbor. The 2.1-mile paved trail is always within sight of the water and is one of...
ME 2.1 mi Asphalt
The 28.9-mile Eastern Trail connects the historic towns along Maine’s southern coast from the woods near Kennebunk to South Portland’s harbor lighthouse. Nearly 22 miles of the route follows off-road...
ME 28.9 mi Asphalt, Crushed Stone, Sand
Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...
ME 2.6 mi Asphalt
The Franconia Notch Recreation Path runs the length of the Franconia Notch State Park in the White Mountain National Forest. Commonly called the Recreation Path, the 8.7-mile trail visits most of the...
NH 8.7 mi Asphalt
Lake Winnisquam is New Hampshire’s fourth largest lake, and taking the Lake Winnisquam Scenic Trail is one of the best ways to experience it. Meaning “pleasant waters,” Lake Winnisquam provides...
NH 1.8 mi Asphalt
The Mountain Division Trail exists as two separate segments of what will eventually be a more than 50-mile-long trail from Fryeburg to Portland. The southern section rolls for about 6 miles between...
ME 9.7 mi Asphalt, Gravel
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
The Norway Branch Rail Trail sits on the former railbed of the Norway Branch Railroad which once connected the communities of Norway and South Paris. The trail runs from Beal Street in the west to...
ME 0.5 mi Crushed Stone
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
About a dozen miles west of Concord, the Stevens Rail Trail offers a quiet, wooded route along the former Concord-Claremont rail line in Contoocook Village. It starts off Krzyzaniak Road and continues...
NH 1.3 mi Dirt, Gravel
he WOW Trail is named after the three bodies of water that can be seen from this rail-trail: Lake Winnipesaukee, Opechee Bay, and Lake Winnisquam. This picturesque 2.7-mile trail shares a corridor...
NH 2.7 mi Asphalt
The 83 acre West Foss Farm is one of the properties owned by the University of New Hampshire, Durham. The property was purchased from the Boston & Maine Railroad company, and features a 1.6 stretch of...
NH 1.6 mi Dirt
The Winnipesaukee River Trail runs along a rail line that previously connected the paper industry between Franklin and Tilton. Nicknamed the Paper City, Franklin saw the industry boom from the 1900s...
NH 5.1 mi Asphalt, Crushed Stone, Dirt, Gravel

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Trails by activity

Lake Winnisquam Scenic Trail

NH - 1.8 miles

Lake Winnisquam is New Hampshire’s fourth largest lake, and taking the Lake Winnisquam Scenic Trail is one of the best ways to experience it. Meaning “pleasant waters,” Lake Winnisquam provides...

Fore River Parkway Trail

ME - 2.6 miles

Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...

Cotton Valley Rail-Trail

NH - 12 miles

The Cotton Valley Rail Trail connects the small town of Wakefield, near the Maine border, and the quintessentially quaint New England vacation town of Wolfeboro. In 2017 the towns held a...

Beth Condon Memorial Pathway

ME - 1.8 miles

The Beth Condon Memorial Pathway is located in the heart of Yarmouth, Maine. The path is named in honor of a high school student who was struck by a drunk driver while walking along US-1. The paved...

Accordion

West Foss Farm Trail

NH - 1.6 miles

The 83 acre West Foss Farm is one of the properties owned by the University of New Hampshire, Durham. The property was purchased from the Boston & Maine Railroad company, and features a 1.6 stretch of...

Eastern Trail

ME - 28.9 miles

The 28.9-mile Eastern Trail connects the historic towns along Maine’s southern coast from the woods near Kennebunk to South Portland’s harbor lighthouse. Nearly 22 miles of the route follows off-road...

Winnipesaukee River Trail

NH - 5.1 miles

The Winnipesaukee River Trail runs along a rail line that previously connected the paper industry between Franklin and Tilton. Nicknamed the Paper City, Franklin saw the industry boom from the 1900s...

Mountain Division Trail

ME - 9.7 miles

The Mountain Division Trail exists as two separate segments of what will eventually be a more than 50-mile-long trail from Fryeburg to Portland. The southern section rolls for about 6 miles between...

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...

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...

Norway Branch Rail Trail

ME - 0.5 miles

The Norway Branch Rail Trail sits on the former railbed of the Norway Branch Railroad which once connected the communities of Norway and South Paris. The trail runs from Beal Street in the west to...

Eastern Promenade Trail

ME - 2.1 miles

Old salts should love the Eastern Promenade Trail, as it skirts the shoreline of Portland’s Casco Bay and Portland Harbor. The 2.1-mile paved trail is always within sight of the water and is one of...

Franconia Notch Recreation Path

NH - 8.7 miles

The Franconia Notch Recreation Path runs the length of the Franconia Notch State Park in the White Mountain National Forest. Commonly called the Recreation Path, the 8.7-mile trail visits most of the...

Stevens Rail Trail

NH - 1.3 miles

About a dozen miles west of Concord, the Stevens Rail Trail offers a quiet, wooded route along the former Concord-Claremont rail line in Contoocook Village. It starts off Krzyzaniak Road and continues...

Back Cove Trail

ME - 3.6 miles

The paved Back Cove Trail rings its namesake tidal basin and offers lovely views of the Portland skyline. You also might spot great blue herons or other birds along the tree-lined waterfront. A...

WOW Trail

NH - 2.7 miles

he WOW Trail is named after the three bodies of water that can be seen from this rail-trail: Lake Winnipesaukee, Opechee Bay, and Lake Winnisquam. This picturesque 2.7-mile trail shares a corridor...

Bayside Trail

ME - 1 miles

Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...

Dover Community Trail

NH - 3.8 miles

The Dover Community Trail snakes its way through the heart of the Garrison City—so nicknamed for the fortified log houses, or garrisons, built by 17th-century settlers—-offering a variety of trail...

WOW Trail

NH - 2.7 miles

he WOW Trail is named after the three bodies of water that can be seen from this rail-trail: Lake Winnipesaukee, Opechee Bay, and Lake Winnisquam. This picturesque 2.7-mile trail shares a corridor...

Franconia Notch Recreation Path

NH - 8.7 miles

The Franconia Notch Recreation Path runs the length of the Franconia Notch State Park in the White Mountain National Forest. Commonly called the Recreation Path, the 8.7-mile trail visits most of the...

Eastern Trail

ME - 28.9 miles

The 28.9-mile Eastern Trail connects the historic towns along Maine’s southern coast from the woods near Kennebunk to South Portland’s harbor lighthouse. Nearly 22 miles of the route follows off-road...

Eastern Promenade Trail

ME - 2.1 miles

Old salts should love the Eastern Promenade Trail, as it skirts the shoreline of Portland’s Casco Bay and Portland Harbor. The 2.1-mile paved trail is always within sight of the water and is one of...

Accordion

Fore River Parkway Trail

ME - 2.6 miles

Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...

Winnipesaukee River Trail

NH - 5.1 miles

The Winnipesaukee River Trail runs along a rail line that previously connected the paper industry between Franklin and Tilton. Nicknamed the Paper City, Franklin saw the industry boom from the 1900s...

Beth Condon Memorial Pathway

ME - 1.8 miles

The Beth Condon Memorial Pathway is located in the heart of Yarmouth, Maine. The path is named in honor of a high school student who was struck by a drunk driver while walking along US-1. The paved...

Mountain Division Trail

ME - 9.7 miles

The Mountain Division Trail exists as two separate segments of what will eventually be a more than 50-mile-long trail from Fryeburg to Portland. The southern section rolls for about 6 miles between...

Norway Branch Rail Trail

ME - 0.5 miles

The Norway Branch Rail Trail sits on the former railbed of the Norway Branch Railroad which once connected the communities of Norway and South Paris. The trail runs from Beal Street in the west to...

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...

Back Cove Trail

ME - 3.6 miles

The paved Back Cove Trail rings its namesake tidal basin and offers lovely views of the Portland skyline. You also might spot great blue herons or other birds along the tree-lined waterfront. A...

West Foss Farm Trail

NH - 1.6 miles

The 83 acre West Foss Farm is one of the properties owned by the University of New Hampshire, Durham. The property was purchased from the Boston & Maine Railroad company, and features a 1.6 stretch of...

Stevens Rail Trail

NH - 1.3 miles

About a dozen miles west of Concord, the Stevens Rail Trail offers a quiet, wooded route along the former Concord-Claremont rail line in Contoocook Village. It starts off Krzyzaniak Road and continues...

Dover Community Trail

NH - 3.8 miles

The Dover Community Trail snakes its way through the heart of the Garrison City—so nicknamed for the fortified log houses, or garrisons, built by 17th-century settlers—-offering a variety of trail...

Cotton Valley Rail-Trail

NH - 12 miles

The Cotton Valley Rail Trail connects the small town of Wakefield, near the Maine border, and the quintessentially quaint New England vacation town of Wolfeboro. In 2017 the towns held a...

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...

Bayside Trail

ME - 1 miles

Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...

Lake Winnisquam Scenic Trail

NH - 1.8 miles

Lake Winnisquam is New Hampshire’s fourth largest lake, and taking the Lake Winnisquam Scenic Trail is one of the best ways to experience it. Meaning “pleasant waters,” Lake Winnisquam provides...

Eastern Trail

ME - 28.9 miles

The 28.9-mile Eastern Trail connects the historic towns along Maine’s southern coast from the woods near Kennebunk to South Portland’s harbor lighthouse. Nearly 22 miles of the route follows off-road...

Winnipesaukee River Trail

NH - 5.1 miles

The Winnipesaukee River Trail runs along a rail line that previously connected the paper industry between Franklin and Tilton. Nicknamed the Paper City, Franklin saw the industry boom from the 1900s...

Eastern Promenade Trail

ME - 2.1 miles

Old salts should love the Eastern Promenade Trail, as it skirts the shoreline of Portland’s Casco Bay and Portland Harbor. The 2.1-mile paved trail is always within sight of the water and is one of...

Franconia Notch Recreation Path

NH - 8.7 miles

The Franconia Notch Recreation Path runs the length of the Franconia Notch State Park in the White Mountain National Forest. Commonly called the Recreation Path, the 8.7-mile trail visits most of the...

Accordion

Stevens Rail Trail

NH - 1.3 miles

About a dozen miles west of Concord, the Stevens Rail Trail offers a quiet, wooded route along the former Concord-Claremont rail line in Contoocook Village. It starts off Krzyzaniak Road and continues...

Lake Winnisquam Scenic Trail

NH - 1.8 miles

Lake Winnisquam is New Hampshire’s fourth largest lake, and taking the Lake Winnisquam Scenic Trail is one of the best ways to experience it. Meaning “pleasant waters,” Lake Winnisquam provides...

West Foss Farm Trail

NH - 1.6 miles

The 83 acre West Foss Farm is one of the properties owned by the University of New Hampshire, Durham. The property was purchased from the Boston & Maine Railroad company, and features a 1.6 stretch of...

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...

Back Cove Trail

ME - 3.6 miles

The paved Back Cove Trail rings its namesake tidal basin and offers lovely views of the Portland skyline. You also might spot great blue herons or other birds along the tree-lined waterfront. A...

Dover Community Trail

NH - 3.8 miles

The Dover Community Trail snakes its way through the heart of the Garrison City—so nicknamed for the fortified log houses, or garrisons, built by 17th-century settlers—-offering a variety of trail...

Fore River Parkway Trail

ME - 2.6 miles

Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...

Beth Condon Memorial Pathway

ME - 1.8 miles

The Beth Condon Memorial Pathway is located in the heart of Yarmouth, Maine. The path is named in honor of a high school student who was struck by a drunk driver while walking along US-1. The paved...

Mountain Division Trail

ME - 9.7 miles

The Mountain Division Trail exists as two separate segments of what will eventually be a more than 50-mile-long trail from Fryeburg to Portland. The southern section rolls for about 6 miles between...

Norway Branch Rail Trail

ME - 0.5 miles

The Norway Branch Rail Trail sits on the former railbed of the Norway Branch Railroad which once connected the communities of Norway and South Paris. The trail runs from Beal Street in the west to...

Bayside Trail

ME - 1 miles

Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...

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...

WOW Trail

NH - 2.7 miles

he WOW Trail is named after the three bodies of water that can be seen from this rail-trail: Lake Winnipesaukee, Opechee Bay, and Lake Winnisquam. This picturesque 2.7-mile trail shares a corridor...

Cotton Valley Rail-Trail

NH - 12 miles

The Cotton Valley Rail Trail connects the small town of Wakefield, near the Maine border, and the quintessentially quaint New England vacation town of Wolfeboro. In 2017 the towns held a...

Recent Trail Reviews

WOW Trail

not great for skating

October, 2020 by benjaminrockwell333

Lots of stop signs involving crossing streets and Frost heaves on the trail. Not a terribly wide trail, expect to go over bricks and wooden Bridges also which are pretty bumpy unless you’re on a bike or something. The other nearby scenic trail is much better

Cotton Valley Rail-Trail

Fantastic Trail for Biking

October, 2020 by leeds.nudd

Very confused at some of the reviews here. Fit mid-30s guy here, though rarely bike, completed the entire trail both ways today on a hybrid rental bike. Yes this trail is gravel and also now plenty of fallen leaves, and it’s perfectly appropriate for a bike ride as long as it’s an appropriate bike. Don’t try to take a road bike with skinny tires on this trail. Enough room along the majority of the trail for bikers to pass each other without stopping, although, yes, once or twice along the 12 mile stretch you may actually need to stop and walk your bike when passing. Such a beautiful ride.

Lake Winnisquam Scenic Trail

great for skating

October, 2020 by benjaminrockwell333

A little more hilly than anticipated but a lot of fun.

Accordion

Cotton Valley Rail-Trail

worst possible trail for bicycles

October, 2020 by moonlightgraham2

Beautiful setting, but clearly not designed for bike riders. Much of the 12 miles of trail (Wolfeboro to Wakefield) runs between the confines of remaining railroad rails, so despite the filled-in smooth surface there is no possibility that riders approaching from opposite directions will have room to pass each other. The many walkers we encountered were all considerate to voluntarily step aside and allow us to pass, although we repeatedly needed to hold up for other riders, giving them the right-of-way. One group of riders that included young children attempting to manage the difficult passages unsupervised caused my wife to take a bad fall. We have used and enjoyed many rail trails in NH -- this one deserves to be crossed off every bicycler's list.

Sawyer River Trail / Sawyer River Road

Very pretty in the fall

October, 2020 by jim_wang

I started from Sawyer River Road parking lot and biked all the way to Swift River near 112 which blocks bike access. So technically you cannot finish the whole trail, even very close. Sawyer River Rd is very good to bike. But think about Sawyer River Trail again before you continue. The trail is not maintained for biking. I had to carry the bike in several locations. There is a big falling tree completely blocking the trail.

The whole trail is very very pretty in the fall. I uploaded some photos.

WOW Trail

No Thanks

September, 2020 by jimmath123

This isn’t really a rail trail. It is a trail that parallels a working rail. A lot of the trail goes through commercial areas, and it is likely you will see homeless people and the less desirable parts of town. More an urban passage. Given where the trail goes, the views are unremarkable.

Rockingham Recreational Rail Trail (Portsmouth Branch)

Not for us

September, 2020 by r2tguy

September 5, 2020. My wife, her friend and I rode this trail yesterday from Massabesic Lake Park to Epping and back. All three of us have eBikes with no suspension, so they're classified as road bikes. All three of us are in our 70s.

The write-up of this trail reads, 'There are a few at-grade road intersections east of town, as the old railbed passes beneath the roads. Some of these underpasses have low ceilings, however, as the bottom of the culverts are planked with wood, so cyclists and equestrians should be prepared to dismount.' The culverts aren't so bad although they are very dark inside. What the write-up fails to mention is that the culverts are at the top of a steep incline about 50 feet high and this incline is strewn with large rocks. It is necessary to push the bike up these inclines and it is extremely difficult going. These inclines need to be made less steep and the rocks need to be removed.

The trail itself is tiring because there are no paved breaks. Parts of the crushed stone trail are smooth, but there's a reason New Hampshire is called the Granite State. While riding it's necessary to keep you eyes on the trail to avoid hitting outcropped rocks. And roots. These are the things that cause bicycles to have flat tires so be sure to bring a flat repair kit with you. Our day was beautiful but the sunlight was shaded on the trail making it difficult to distinguish the rocks and roots in the shadows.

This trail would be beautiful in October with the fall colors but it would be a sure bike basher because the fallen leaves will further hide the outcropped rocks and roots. I had to stop along the trail to tighten a screw on the right side of my bike that holds the rear fender brace and luggage rack. On the way back the screw on the left side had vibrated completely out so my bike was falling apart on this trail.

To make matters worse we ran out of battery power on the way back and our bikes weigh about 60 pounds! Not fun.

Perhaps much younger and more athletic folks with fat tire bikes would enjoy this trail but it was not for us.

P.S. In Epping the DG Cycle Sports shop is very near the trail. We had lunch at The Beach Plum, which is our favorite restaurant for lobster rolls and fried clams.

Northern Rail Trail

Boscawen to Highland Lake

September, 2020 by aldcon_tl

Parked at lot at ballfield at end of Depot Street in Boscawen. Go to very end of Depot Street and lot is on the right. Took trail for about 16 miles to town beach at Highland Lake on Channel Road. Slightly uphill all the way. Very few soft spots. In general all trail all packed gravel. Public beach also at Webster Lake ( about 13 miles from Depot St.).

Rockingham Recreational Rail Trail (Portsmouth Branch)

Worth the trip !

August, 2020 by rgbww

I rode from the East end in Newfield, and went as far as the East Candia Depot parking lot. My odometer had it at 17 miles.
The trail is tree lined for the vast majority of the way. A nice spot to take a break was at Onway Lake, 15 mile point.
There are two major road crossings, but other than that the crossings are on residential roads with minimal traffic.
Go and enjoy it !!

Dover Community Trail

Enjoyable, Difficult to Follow at Points

August, 2020 by rscote05

My husband, my dog and I walked the trail this weekend. The weather was perfect. The trail is really three separate sections. We parked at the Watson Rd entrance and that portion terminated at the end of Whittier Falls Way. You then cross the street to find the unmarked second entrance into a field. You follow that until it comes out at 4th St. The third portion of the trail starts at the end of the parking lot of the Dover Transportation Center and ends at Fisher St. We were able to navigate it by referencing the map in the App. River views were pretty and it was relatively flat.

Mountain Division Trail

great bike ride!

August, 2020 by meryl.block.weissman

The family all loved this rail trail. The unpaved section was a bit hilly and rocky (about 1 mile). The paved section ran parallel to the train tracks. Really cool bridge over the water. Also stopped by the Orchard Ridge farm along the way. Visited the animals and had tasty donuts, fudge and cheese.

Warren to East Haverhill Railroad Grade Trail

warren to east haverhill

August, 2020 by flintpitas

The trail only exists for snow mobiles.

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