Explore the best rated trails in Wolfeboro, NH. Whether you're looking for an easy walking trail or a bike trail like the Eastern Promenade Trail and Stevens Rail Trail. With more than 45 trails covering 346 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
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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...
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 South Manchester Rail Trail is a proposed bike/pedestrian path that would connect the downtown Millyard area of Manchester to the Town on Londonderry. The South Manchester Rail Trail will utilize...
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...
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 Piscataquog Trail, though only about 2 miles long, provides a vital off-road link between the communities on the western side of the Merrimack River (the West Side of Manchester) to several parks...
The Peanut Trial is a distinct trail in the town of Newton that spans one-mile. This rail-trail was meant to connect to the Jay McLaren Memorial Trail. However, due to a controversial lawsuit by land...
This exquisitely maintained trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. The trail will eventually be part of the Granite State Rail Trail,...
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...
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...
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 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 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 Roland Bergeron Bike Path runs about 6 miles alongside nearly the entirety of Albuquerque Avenue in Litchfield, NH. Completed in 2010, the 8-ft wide asphalt path averages about 5 yards in from...
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...
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The Heritage Trail is managed by the state of New Hampshire to provide access to recreational and historical attractions across the state. Eventually, the north-south route along the former Boston and...
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...
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 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 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 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 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 New Boston Rail Trail follows the former railroad corridor of the same name for 3.9 miles through densely wooded areas in the town of New Boston. The railroad was in operation from 1893 to 1931,...
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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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...
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 Roland Bergeron Bike Path runs about 6 miles alongside nearly the entirety of Albuquerque Avenue in Litchfield, NH. Completed in 2010, the 8-ft wide asphalt path averages about 5 yards in from...
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 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 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...
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 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 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 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 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 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...
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...
Hillsborough Recreational Rail Trail connects three communities in south-central New Hampshire: Hillsborough, Deering, and Bennington. The unpaved trail winds along the Contoocook River through rural...
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 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...
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 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...
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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 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 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 Roland Bergeron Bike Path runs about 6 miles alongside nearly the entirety of Albuquerque Avenue in Litchfield, NH. Completed in 2010, the 8-ft wide asphalt path averages about 5 yards in from...
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 Piscataquog Trail, though only about 2 miles long, provides a vital off-road link between the communities on the western side of the Merrimack River (the West Side of Manchester) to several parks...
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 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 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...
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 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 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 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 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 Peanut Trial is a distinct trail in the town of Newton that spans one-mile. This rail-trail was meant to connect to the Jay McLaren Memorial Trail. However, due to a controversial lawsuit by land...
Wife and I started in Hanover and went 15 miles the turned around and came back. Beautiful streams and lake on the way. Trail wasn’t crowded on this Thursday.
The trail is extremely sandy. Some parts are packed sand but many sections are like the beach. Great for ATVs, I suppose. Not great for bikes, even a mountain bike. If you do choose a mountain bike, do know that ATVs will be frequently passing you.
we parked by the closed plant on Davidson drive.
trail started off soft, some areas quite wet and rutty. Plenty of rocky spots too that make even riding the fat tire bike tough. Trail doesn't appear to be maintained very well. However, there was a nice waterfall off to the side of the trail.
Headed east 10 miles from Lake Massebesic. Trail surface was rutted and very bumpy. Frequent large rocks sticking up and some wet/muddy areas. Not pleasant riding on a touring bike with 32mm tires. A fat bike or full suspension mountain bike would be a better choice. Four long culvert underpasses were too low to walk upright. Generally not much fun. I rode back mostly on parallel roads (which were very nice).
Parked at the Windham Post office and followed the train tracks about 5 miles. Paved trail follows the tracks on the segment I rode on. Part of the trail was still blocked by snow and impassable by bike. Looking forward to riding much further when the snow is gone! Trail goes through woods, past farms and fields and leads to a dam. There’s a small farm called Orchard Ridge along the trail to get drinks and snacks. Lots of quiet neighborhoods to ride around in as well.
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.
This is a difficult trail to assign a star rating to as parts of it are great and parts are not. It’s listed as a 29 mile trail but in reality it is split into 5 sections with 2 sections being on busy roads. I’ll break it down by section starting at the southern end in Kennebunk. I. 6-mile off-road section from Kennebunk to Biddeford - 5 stars. This is a great section featuring a well-maintained hard packed dirt trail through the woods. II. 5 mile on-road section through Biddeford and Saco - 2 stars. The first couple of miles are okay as you can ride on a sidewalk and residential streets. If you just do the first couple of miles combined with the first 6 mile off road section, it’s a nice 16 mile round trip. The issue is the next 2.5 miles is on busy roads through the congested areas of Biddeford and Saco. III. 7 mile off-road section from Saco to Scarborough - 5 stars. I’ve been on dozens of trails throughout the Northeast and this is one of my favorites. The trail is hard packed and is in great condition and features a stretch through the scenic Scarborough marsh. IV. 4 mile on-road section from Scarborough to South Portland - 1 star. The first half mile is fine as it’s on a lightly traveled road. But after that, it’s 3+ miles on busy roads that are narrow in spots. I’ve only been on the stretch once and several times a car came with a couple of feet of me - no interest in doing this section again. V. 6 mile off-road section in South Portland - 3 stars. It’s certainly better than riding the streets of Portland or South Portland. But there’s just nothing special about - nothing too scenic until you hit the very end, the trail is in decent, not great, shape, and it’s not well marked. But the biggest negative is the number of times the path crosses busy streets - I’ve never been on another trail with so many busy street crossings over a short stretch. So, the star rating of the trail depends on what you are looking for. If you’re looking to do a round trip of around 15 miles or less, there are two sections that are great - Kennebunk to Biddeford and Saco to Scarborough. If you’re looking to do more than that, you’ll have to deal with at least a few miles of busy streets.
Great walk along the riverside. Mostly level, flat and paved surface. Easy walking and quite quiet for a Saturday. Great day for a walk along the river.
We started at airport and went out 2.5 miles and then turned around. Easy path, smells wonderful, leaf changing colors breathtaking! We loved the scannable QR codes that teach you along the way about plants, trees, sites etc. we learned quote apt!
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!
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