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 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...
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 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 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...
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...
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. Trail development began in 1996 after the state purchased the Boston and Maine...
The Old Railroad, as its name suggests, is a multi-use trail that occupies a former Boston & Maine Railroad corridor. The trail picks up at the northern trailhead of the Common Pathway, a paved...
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 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...
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...
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...
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 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...
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 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 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...
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...
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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.
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...
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 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...
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 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 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...
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...
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 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...
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. Trail development began in 1996 after the state purchased the Boston and Maine...
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 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...
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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 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...
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...
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....
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 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...
Spanning 57.6 miles from Lebanon to Boscawen, the Northern Rail Trail is New Hampshire’s longest rail-trail conversion. Trail development began in 1996 after the state purchased the Boston and Maine...
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 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...
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 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...
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 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 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 Old Railroad, as its name suggests, is a multi-use trail that occupies a former Boston & Maine Railroad corridor. The trail picks up at the northern trailhead of the Common Pathway, a paved...
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...
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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...
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.
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 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...
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....
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...
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 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...
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.).
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.
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.
The trail only exists for snow mobiles.
We rode from Wolfeboro 7 miles out and back with our three kids. I was very nervous after reading the reviews of people getting hurt. We almost didn’t do this trail because of the reviews. The part we rode was great! Yes, there are parts where you have to switch between the trail and the track but if you are careful and SLOW down this is not an issue. The trail is mostly flat with great scenery . I say a it’s a great trail!
A real treat! Lovely views of lake for first 1/2 mi. Park at Osborne’s on Rte 3. Perfect for biking, although some sharp bends.
I parked on Fisher street, you have to park on side of the road. The first .6 mile is beautiful, clean. Nice view of Dover from the bridge. You come out at the train station and have to find the trailhead on fourth street. I passed the trailhead several times as it isn’t marked. It is right before the bridge on the right past the energy company. Be careful if on a bike as it is a steep down hill followed by lots of tree roots. I walked my bike past that part, the water is to your left. The path then becomes grassy thru a field and comes out to another street. I turned around at that point as I wasn’t sure which way. Lesson learned, get a map before riding on this trail.
Start in Franklin. Very pleasant. Skip Tilton — trail there is poorly marked, poorly maintained, and felt unsafe if I had been alone.
I’ve ridden and walked all over this trail over the years as a local yocal. The portion from downtown Wolfeboro to Fernald station is basically for walkers/joggers only. There are a ton out all times of the year and rightfully so, it’s mint. I got an e-bike recently, and have found the portion from Fernald Station in Wolfeboro out to Wakefield is the best for bikes. It’s crushed stone the entire way and limited foot traffic. Picnic tables along the way too with spots to chill.
The trail is a continues incline but not steep. There are quite a few railroad ties after the first mile but the there is room to go around in most places. Effortless return due to the down slope.
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