Find the top rated walking trails in Hillsborough, 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 Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...
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 Nashua River Rail Trail stretches from southern Nashua, New Hampshire, to downtown Ayer, Massachusetts, connecting to the towns of Pepperell and Groton. The trail is built on the former rail...
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 smooth paved surface of the Londonderry Rail Trail offers a pleasant, tranquil 4.5-mile adventure for trail users in south-central New Hampshire. Its route follows a corridor once used by the...
Mine Falls Park in Nashua is a 300-acre-plus urban park with a network of approximately 9.7 miles of a variety of trail types. This forested park offers an extraordinary nature experience in the heart...
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
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 Toonerville Rail-Trail shadows the Black River for most of its 3.2-mile length in eastern Springfield to the border with New Hampshire across the Connecticut River. The route originally carried an...
The North Central Pathway is envisioned as a trail network connecting points of interest through and between Winchendon and Gardner. Several completed sections of trail make for a lovely ride or walk...
The Mascoma River Greenway is a planned 4-mile non-motorized pathway through the heart of Lebanon. The trail is envisioned to link West Lebanon to the Northern Rail Trail, which spans more than 50...
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 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 Windham Rail Trail passes through the woodsy periphery of Windham in southern New Hampshire, but it sits in the heart of the future cross-state Granite State Rail Trail. Its connections to the...
Mile 0.0 - DPW Garage Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
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 Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line 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...
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection between Wheelock Park on the trail's west end and Ashuelot River...
Nestled in the woodlands on the northern end of Merrimac in the far northeastern corner of Massachusetts, lies the beautiful Jay McLaren Memorial Trail. The town, once known as West Amesbury, had a...
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 Harrisville Rail Trail runs for just under two miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris...
When complete, the Salem Bike-Ped Corridor will run for more than 5 miles on a former Boston and Maine Railroad corridor from connections with the Windham Rail Trail (north) and Methuen Rail Trail...
The Monadnock Recreational Rail Trail is a great example of a repurposed rail route that provides safe commuting opportunities while also allowing trail users to escape into forest environments for...
The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...
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...
Lowell's Canal System Trails are part of Lowell National Historical Park in Lowell, Massachusetts. The park preserves some of America's industrial past: its 19th-century textile mills formed the first...
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 Bobby Woodman Rail Trail, a hard-packed dirt and gravel pathway, begins off a quiet street at the southern end of Claremont and quickly dives under pleasant tree cover. After about a half mile,...
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 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...
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...
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,...
Mine Falls Park in Nashua is a 300-acre-plus urban park with a network of approximately 9.7 miles of a variety of trail types. This forested park offers an extraordinary nature experience in the heart...
Mile 0.0 - DPW Garage Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...
The North Central Pathway is envisioned as a trail network connecting points of interest through and between Winchendon and Gardner. Several completed sections of trail make for a lovely ride or walk...
The Cross Vermont Trail (CVT) is a statewide route that links a number of Vermont trails and includes on-road sections. As of January 2016, 87 miles of trail are built and scattered across the state....
The North Central Pathway is envisioned as a trail network connecting points of interest through and between Winchendon and Gardner. Several completed sections of trail make for a lovely ride or walk...
The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...
The Harrisville Rail Trail runs for just under two miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris...
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 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...
Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection between Wheelock Park on the trail's west end and Ashuelot River...
The year 2017 marks 20 years since a rails-to-trails project was first mentioned in the Goffstown Master Plan, and thanks to work by the Friends of the Goffstown Rail Trail and support throughout the...
Visitors to the Sugar River Trail (also known as the Sugar River Recreational Rail Trail) can be forgiven if they lose track of which side of the river they’re traveling. The 9.5-mile trail crosses...
The Haggetts Rail Trail is a short, but sweet unpaved trail located on the periphery of Haggetts Pond, the local reservoir for the nearby town of Andover. Built on part of the former line of the...
More than a mile of the Ashburnham Rail Trail opened in 2015 from a point just south of Ashburnham's center to Turnpike Road. The rustic route, planned to be paved in the future, offers a...
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...
Barker Road Trail begins on the town line between North Andover and Boxford in northern Massachusetts, not far from the New Hampshire border. From there, the pathway continues through dense woodlands...
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 Mascoma River Greenway is a planned 4-mile non-motorized pathway through the heart of Lebanon. The trail is envisioned to link West Lebanon to the Northern Rail Trail, which spans more than 50...
The Toonerville Rail-Trail shadows the Black River for most of its 3.2-mile length in eastern Springfield to the border with New Hampshire across the Connecticut River. The route originally carried an...
The Monadnock Recreational Rail Trail is a great example of a repurposed rail route that provides safe commuting opportunities while also allowing trail users to escape into forest environments for...
Jonathan Daniels Trail travels the length of Ashuelot River Park through Keene. Along the stone-dust trail, you can enjoy the park’s beautiful natural backdrop and flower garden. The trail was named...
Mile 0.0 - DPW Garage Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...
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 Bobby Woodman Rail Trail, a hard-packed dirt and gravel pathway, begins off a quiet street at the southern end of Claremont and quickly dives under pleasant tree cover. After about a half mile,...
Great trail. Wonderful walk but, caution, it reads as 3 miles on the surface. It is actually 7. Once you read all the detail you see that 4 miles more through Brookline.
Parked at the Troy depot heading south toward Fitzwilliam and encountered a huge deep puddle a short distance away, there was no way around it and I had to turn around. It had been really dry, surprised to see a puddle
Where this trail starts in downtown Nashua is not a great area. We biked it recently to get access to the Mine Falls Park. About half way down the trail is better but would probably have to park on a street. If you are looking for a nice bike ride I suggest the Nashua River trail. Mine Falls is nice but you are in the minority if you are biking. There are a lot of walkers.
Absolutely gorgeous views for autumn folliage! Very easy. We went up via road bikes, parking at the West Side Ice Arena. Easy to navigate, only wish is that it was longer!
Took our ATVS down this trail today. Very well groomed, mainly flat surface (dirt and gravel). There is a large parking lot to unload. The trail signage was a bit confusing at times—one sign saying ATVS were permitted and others saying prohibited. If you park at the Fish and Game Road the trail head on the right takes you down a pretty short trail—so I would recommend starting on the left trail head which is decent in length. V
I just went to Black Jack Crossing road. There is no parking. Where is someone parking a horse trailer to get on this side of the trail?
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.
This trail is perfect for riding your bike through the woods, fun and scenic!
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