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 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 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 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...
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 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 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 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...
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...
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...
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 Village Spur Rail Trail begins in downtown Belmont, and stretches from behind the Belmont Mill to the Tioga River on the west side of South Road. Out and back for the entire trail is about four...
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...
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...
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 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...
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 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 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...
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...
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...
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...
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....
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...
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 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...
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 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 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...
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 Village Spur Rail Trail begins in downtown Belmont, and stretches from behind the Belmont Mill to the Tioga River on the west side of South Road. Out and back for the entire trail is about four...
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...
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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 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 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 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...
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...
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 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 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...
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 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 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...
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 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...
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...
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...
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...
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 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 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...
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...
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...
goes by some lakes and marsh areas. Different as it goes on and off between rails filled with sand and gravel. beautiful spot at the end with lake winnepasaki.
The trail has been extended 0.4 miles south of Fisher Street, though there is no obvious parking at that end. Start near the south end, so you can partially coast on the return.
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!
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.
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.
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!
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
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.
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.
Went to epping with ATV says no ATV only winter time . App doesn't mention that
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
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