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 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...
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...
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 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 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...
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 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...
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 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 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 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...
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...
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 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...
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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.
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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...
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 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 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 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 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...
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 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...
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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 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...
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...
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 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 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...
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...
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...
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 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 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...
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 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...
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...
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 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...
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...
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...
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 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 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...
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 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 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 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...
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...
We did this in two parts: Kennebunk-Biddeford, and South Portland-Saco. To do just Kennebunk to Biddeford & back is a bit too easy and dull - straight, flat, 12 miles round trip; although, you might want to reserve time to explore downtown Biddeford. Biscuits! Doughnuts! Brewery! Etc.
The Portland-Saco stretch is more varied. If you start from Bug Light Park, like we did, I think it comes out to more than 20 miles; for a shorter ride, start from the parking lot on the trail proper. There is the most excellent empanada place in Saco where you should try to have lunch. The marsh is fun with interesting birds.
Interesting to be able to see the entire loop from the starting point. Only one real incline at the overpass. We added an out and back on Eastern Promenade Trail to get 9.9 total miles.
After reading the reviews I decided to ride this trail as it was a beautiful Sunday afternoon in August. Perfect weather for a bike ride. I decided to bring my mountain bike and I am glad I did (I usually ride my hybrid for Rail Trails.)
I parked in Wolfeboro. Started out my ride at 1:00 PM. Tons of other riders and walkers, a few runners.. The first few miles were beautiful crossing the cog-ways but frustrating with all the other people on the trail. It is narrow and yes, when you are riding in between the rails as noted in other reviews, it can be a bit hairy when other bikers or STOLLERS are coming the other way. If the other biker didn't look very experienced or they were kids I stopped to let them pass. Had to do this several times. I was having second guesses with all the foot traffic but after a few miles it lessened a bit, just a bit, and the scenery was so peaceful. I got to Route 16, and yes the traffic was fast and heavy enough that I decided it wasn't worth it. Plus I'm out of shape and knew I had another 11 miles to go to get back!
I was wondering if I was going to encounter the same traffic going back especially the closer to Wolfeboro I got, but happily the ride back was 100% better. Maybe because is was now 2:30 ish..
There were still plenty of people on the trail but not half as many and I didn't have to stop once.
I loved this trail, but think I will come back again in the fall or during the midweek with less people.
This trail is the best maintained trail I have ever been on. Completely smooth gravel and the edges were just mowed. The hybrid bike would have been fine except the rail crossings.
The rail crossings were never a problem for me but probably because I had the mountain bike with shocks. I would be more cautious if I had the hybrid! Just go slow and be careful. Common sense..
Last thought, if I didn't live 45 minutes from Wolfeboro, this trail would be perfect for running!! Traffic or not!
We rode about 26 miles total. 13 miles there & back. Crushed stone most of the way..We parked in Lebanon parking lot,where it begins. Little grassy in sections.Gets wider in some spots & pretty narrow in some areas. We thought the first 10 miles were nice ,then it was a very narrow trail & buggy.lot of small bridges,some were in need of repair,need to pay attention.There was an area were the rail road ties were exposed about 10 miles from beginning.Just have to watch out..Rode past some lakes& huge rocks that were blasted out for trains..Was a pretty trail .. Could get muddy if rain ..
We biked and geocached this section today. We had an enjoyable ride, but the surface was quite varied. Nothing was paved. We started out on well packed gravel/ dirt on a wide trail, but by the time we were at the other end, following the river, it was single track, mostly through grass, with some roots and a few sandy patches. It didn't resemble most of the rail trails I have been on, but my hybrid bike was fine, and we really enjoyed the variety.
Last July, I reported that the bridges were a pretty sketchy to go over with horses. I am so happy to report that the bridge's planks have been replaced. I've ridden several days lately and each time the gentlemen brush-hogging were so polite turning off their motors so they wouldn't spook the horses. All the bikes and hikers I have met are so sweet and friendly. I just love to ride my horses on this trail. Thank you to whomever is responsible for maintaining the P R/T!
While this is a great trail for hiking my husband and I felt it was way too narrow to share with bikers and hikers. We had to stop riding whenever someone was coming in the opposite direction. We found we were too busy concentrating to enjoy the views. Not a good bike trail.
My wife and I road from Newfields to Rt. 125 and then back (the eastern part of the trail). The trail was in good shape and we saw turtles and raccoons. We were on Hybrids, but saw other people on road bikes. Others were walking and some jogging. All in all a beautiful day to be out on the trail.
My wife and I had our first experience biking this trail this week. We found it very enjoyable until we both had a bad accident. There are several areas on the trail where you have to cross the rails which are sticking above grade and will through you off the bike.
I sustained a 2 inch laceration and multiple abrasions and contusions which required an ER visit. My wife injured her shoulder and knee.
After reading past reviews complaining of this same problem over several years, I can not understand why this problem has not been corrected since it would be easy to remedy!!! Disappointed that peoples safety is not of paramount importance!!
I hope that this will be addressed in the near future.
I did this in the summer of 2018. as others have mentioned, quite rough in spots. quite wet in spots. and sandy, i hate sandy.
could be a nice trail but as it is, i wouldn't recommend it for bikes, even a mountain bike. also, beware of the dogs.
with the exception of the Northern Rail Trail, New Hampshire needs to step up their game regarding their rail trails.
We started our ride at the Hannah Duston parking lot in Boscawen. The RTC map takes you to where the ride starts but not the parking area. The parking area is shortly after you get off I-93. It's a Park and Ride lot. There are good signs to indicate which way the ride starts. It starts 0.5 miles down the street. The first mile or so is out in the open. After that, it goes into a shaded area. At this time of year, the mosquitoes are plentiful and ready to bite. The surface of the trail is crushed gravel and easily ridden with a hybrid or mountain bike. Sadly, we had to cut our ride short after about 5 miles due to a bike malfunction. We plan to go back and give it another try. An additional point of interest is the monument to Hannah Duston, which is located to the left of the trailhead kiosk, across a little bridge. It sits on the banks of the Merrimack River.
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