Find the top rated walking trails in Ossipee, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
The 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...
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...
The 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...
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...
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...
The Franconia Brook Trail runs from just north of the confluence of the east branch of the Pemigewasset River and Franconia Branch. Note that bicycling is not permitted along the route. You can...
The trestle trail is part of a network of rail-trails converted from and old logging railroad in the White Mountains. It is close to the Zealand Trail, the Sugarloaf Trail, and the Hale Brook...
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Crossing through wooded areas and featuring magnificent wetland vistas, the Rockingham Recreational Rail Trail (Fremont Branch) offers an 18.3-mile trail adventure from Epping to Windham. The northern...
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...
The Oliverian Brook Trail follows the course of Oliverian Brook through the dense forest of White Mountain National Forest. The trail, open to cross-country skiing in winter, heads toward Passaconaway...
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...
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...
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...
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...
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...
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...
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Bicycles are permitted only on the first 2.3 miles of the trail, up to the wilderness boundary (marked with signs). Hiking and cross-country skiing only are allowed past this point.
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...
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...
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...
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...
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...
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...
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...
The 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...
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...
The Head’s Pond Trail (formerly known as Hooksett Rail Trail) is a 1.9-mile rail-trail that visits two scenic ponds, including the eponymous Head’s Pond, in a woodsy area of Hooksett. The trail’s...
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...
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...
The Oliverian Brook Trail follows the course of Oliverian Brook through the dense forest of White Mountain National Forest. The trail, open to cross-country skiing in winter, heads toward Passaconaway...
The trestle trail is part of a network of rail-trails converted from and old logging railroad in the White Mountains. It is close to the Zealand Trail, the Sugarloaf Trail, and the Hale Brook...
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...
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...
Crossing through wooded areas and featuring magnificent wetland vistas, the Rockingham Recreational Rail Trail (Fremont Branch) offers an 18.3-mile trail adventure from Epping to Windham. The northern...
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....
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...
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The Rockingham Recreational Rail Trail brings at least two superlatives to mind: it’s one of New Hampshire’s longest rail-trails at just more than 28 miles, and it begins in Manchester, the state’s...
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...
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...
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...
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...
I rode this trail on my mountain bike with my 3yr old nephew in the rear-mounted toddler seat. Excellent ride with terrific views, plenty of spots to safely pull aside, if necessary. Yes, as others have said, the trail does get narrow on the causeway. However, visibility is excellent. One has plenty of time to adjust their position for oncoming riders & pedestrians. The transitions over the rails are very well marked. The transitions should cause no issues for a mountain bike, hybrid or gravel bike. This would not be a trail for a true road bike with slicks or narrow tires, as a rule. Rode mid-week at the height of summer with no issues navigating other users. Enjoy!
I have ridden this trail in increments, in 10ish mile out and back segments, and have enjoyed each ride a great deal. I have the last bit to finish still, a section in the middle where parking was not as clear to me initially. I hope to repeat it as a full ride at some point just to say I did it. Spring, Summer, Fall, all beautiful, and the covered bridges and historic areas are a nice surprise. The incline is so gradual, you don't realize it until you turn around and head back and finish a bit quicker on the return. It's busier at the Lebanon end but not packed by any means, and the Loons were a real treat.
The is was my first event with the MeetUp organization. It was a 40 mile ride with a great group of people. I was the “geezer” and everyone was extremely friendly and helpful. And as soon as Winter is over, I want to do more of these trips.
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
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.
A little more hilly than anticipated but a lot of fun.
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.
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.
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.
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.
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.).
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