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Rockingham, VT Hiking Trails and Maps

538 Reviews

Looking for the best Hiking trails around Rockingham?

Find the top rated hiking trails in Rockingham, whether you're looking for an easy short hiking trail or a long hiking trail, you'll find what you're looking for. Click on a hiking trail below to find trail descriptions, trail maps, photos, and reviews.

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Length
Most Popular

Ashuwillticook Rail Trail

13.7 mi

State: MA

Asphalt

Bridge of Flowers

0.1 mi

State: MA

Concrete

Canalside Rail Trail

3.6 mi

State: MA

Asphalt

Goffstown Rail Trail

5.5 mi

State: NH

Dirt, Grass, Gravel, Sand

Harrisville Rail Trail

1.6 mi

State: NH

Dirt

Jonathan Daniels Trail

0.9 mi

State: NH

Crushed Stone

Mascoma River Greenway

2.78 mi

State: NH

Asphalt, Gravel

Monadnock Recreational Rail Trail

7.5 mi

State: NH

Asphalt, Gravel

Northern Rail Trail

57.8 mi

State: NH

Cinder, Crushed Stone

Old Railroad Trail

2.7 mi

State: NH

Dirt

West River Trail

16.1 mi

State: VT

Asphalt, Dirt, Gravel, Sand

Ashuelot Recreational Rail Trail

21.5 mi

State: NH

Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Bobby Woodman Rail Trail

1.7 mi

State: NH

Dirt, Gravel

Cheshire Rail Trail (Cheshire Branch Rail Trail)

32.9 mi

State: NH

Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Common Pathway

5.5 mi

State: NH

Asphalt, Crushed Stone

Concord-Lake Sunapee Rail Trail

5.65 mi

State: NH

Asphalt, Boardwalk, Crushed Stone, Dirt, Gravel

Delaware and Hudson Rail-Trail

25.8 mi

State: NY, VT

Asphalt, Cinder, Dirt, Grass, Gravel

Fort Hill Recreational Rail Trail

7 mi

State: NH

Ballast, Cinder, Dirt, Gravel, Sand

Granite Town Rail-Trail

3 mi

State: NH

Ballast, Cinder, Dirt, Grass, Gravel, Sand

Hoosic River Greenway

2.5 mi

State: NY

Gravel

Accordion

Lye Brook Falls Trail

2.2 mi

State: VT

Gravel

Mason Railroad Trail

6.7 mi

State: NH

Ballast, Gravel, Sand

New Boston Rail Trail

3.9 mi

State: NH

Dirt

North Central Pathway

11.2 mi

State: MA

Asphalt

Stevens Rail Trail

1.65 mi

State: NH

Crushed Stone, Gravel

Sugar River Trail

9.5 mi

State: NH

Ballast, Gravel, Sand

Toonerville Rail-Trail

3.2 mi

State: VT

Asphalt

Winnipesaukee River Trail

5.1 mi

State: NH

Asphalt, Crushed Stone, Dirt, Gravel

Hillsborough Recreational Rail Trail

7.8 mi

State: NH

Crushed Stone, Dirt

Hoot, Toot and Whistle Trail & Riverwalk

2.3 mi

State: VT

Dirt

Ware River Rail-Trail

12 mi

State: MA

Ballast, Dirt, Grass, Gravel

Appel Way Trail

1.3 mi

State: NH

Asphalt

Ashburnham Rail Trail

1.3 mi

State: MA

Dirt

Valley Trail

9.1 mi

State: VT

Asphalt, Dirt, Gravel

Bennington Rail Trail

1.65 mi

State: VT

Asphalt, Crushed Stone, Gravel

Brookline Rail Trail

4.5 mi

State: NH

Crushed Stone, Gravel

Catamount Trail - Sections 1 and 2

18.1 mi

State: VT

Dirt

East Branch Trail (VT)

0.5 mi

State: VT

Gravel

Henniker & Hopkinton Rail Trails

6.7 mi

State: NH

Dirt, Grass, Gravel, Sand

Keene Industrial Heritage Trail

1 mi

State: NH

Asphalt

Merrimack River Greenway Trail

0.33 mi

State: NH

Asphalt

Warner Rail Trail and Bagley Rail Trail

1 mi

State: NH

Crushed Stone, Gravel

Trail Image	Trail Name	States	Length	Surface	Rating
	Ashuwillticook Rail Trail Overview Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along a 13.7-mile paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through...	MA	13.7 mi	Asphalt	100 reviews
	Bridge of Flowers The Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...	MA	0.1 mi	Concrete	4 reviews
	Canalside Rail Trail 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...	MA	3.6 mi	Asphalt	13 reviews
	Goffstown Rail Trail 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...	NH	5.5 mi	Dirt, Grass, Gravel, Sand	15 reviews
	Harrisville Rail Trail 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...	NH	1.6 mi	Dirt	1 reviews
	Jonathan Daniels Trail 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...	NH	0.9 mi	Crushed Stone	1 reviews
	Mascoma River Greenway The Mascoma River Greenway is a planned 4-mile rail-trail through the heart of Lebanon. The paved, multiuse trail is currently 2.78 miles, offering a pleasant opportunity for both recreation and...	NH	2.78 mi	Asphalt, Gravel	2 reviews
	Monadnock Recreational 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...	NH	7.5 mi	Asphalt, Gravel	20 reviews
	Northern Rail Trail Overview Spanning nearly 58 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...	NH	57.8 mi	Cinder, Crushed Stone	69 reviews
	Old Railroad Trail 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...	NH	2.7 mi	Dirt	1 reviews
	West River Trail The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...	VT	16.1 mi	Asphalt, Dirt, Gravel, Sand	13 reviews
	Ashuelot Recreational Rail Trail Closure Notice: Due to flooding, the Ashuelot Recreational Rail Trail is closed from Pine Street to Sawyer's Crossing Road in Swanzey. Please see NH State Parks for more up-to-date information. The...	NH	21.5 mi	Asphalt, Ballast, Cinder, Crushed Stone, Dirt	41 reviews
	Bobby Woodman Rail Trail 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,...	NH	1.7 mi	Dirt, Gravel	1 reviews
	Cheshire Rail Trail (Cheshire Branch Rail Trail) Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9...	NH	32.9 mi	Asphalt, Ballast, Cinder, Dirt, Gravel, Sand	45 reviews
	Common Pathway The Common Pathway travels 5.5 miles from the outskirts of Peterborough south to downtown’s Noone Falls area, paralleling US 202 and the Contoocook River for most of its journey. The small town of...	NH	5.5 mi	Asphalt, Crushed Stone	8 reviews
	Concord-Lake Sunapee Rail Trail Following the historic Concord-Claremont Railroad corridor, the Concord–Lake Sunapee Rail Trail will eventually connect communities from Concord to the southern point of Lake Sunapee via a multiuse...	NH	5.65 mi	Asphalt, Boardwalk, Crushed Stone, Dirt, Gravel	1 reviews
	Delaware and Hudson Rail-Trail The Delaware and Hudson Rail-Trail follows the flowing contours of the western Vermont countryside, rambling in and out of New York state, where you’ll find a 4-mile gap. This border area is known as...	NY, VT	25.8 mi	Asphalt, Cinder, Dirt, Grass, Gravel	31 reviews
	Fort Hill Recreational Rail Trail 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...	NH	7 mi	Ballast, Cinder, Dirt, Gravel, Sand	12 reviews
	Granite Town Rail-Trail Overview The Granite Town Rail-Trail runs for 3 miles in Milford, New Hampshire. Portions of the route are unpaved and surfaced with sand, gravel, and/or dirt, while short concrete sections can be...	NH	3 mi	Ballast, Cinder, Dirt, Grass, Gravel, Sand	3 reviews
	Hoosic River Greenway The Hoosic River Greenway spans 2.5 miles along the river’s east bank through the Village of Hoosick Falls. The gravel pathway follows the former route of the Boston Hoosac Tunnel & Western Railway,...	NY	2.5 mi	Gravel	4 reviews

Accordion

Lye Brook Falls Trail The heavily wooded Lye Brook Falls Trail runs for 2 miles through the Lye Brook Wilderness of the Green Mountain National Forest near Manchester. The blue-blazed hiking trail follows the bed of a...	VT	2.2 mi	Gravel	9 reviews
Mason Railroad Trail The Mason Railroad Trail runs for nearly 7 miles from near the New HampshireMassachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...	NH	6.7 mi	Ballast, Gravel, Sand	18 reviews
New Boston Rail Trail 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,...	NH	3.9 mi	Dirt	7 reviews
North Central Pathway 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...	MA	11.2 mi	Asphalt	25 reviews
Stevens Rail Trail The Stevens Rail Trail is part of the Concord-Lake Sunapee Rail Trail, which follows the historic Concord-Claremont Railroad corridor. Located about a dozen miles west of Concord, the Stevens Rail...	NH	1.65 mi	Crushed Stone, Gravel	3 reviews
Sugar River Trail 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...	NH	9.5 mi	Ballast, Gravel, Sand	28 reviews
Toonerville Rail-Trail 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...	VT	3.2 mi	Asphalt	7 reviews
Winnipesaukee River Trail 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...	NH	5.1 mi	Asphalt, Crushed Stone, Dirt, Gravel	21 reviews
Hillsborough Recreational Rail Trail 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...	NH	7.8 mi	Crushed Stone, Dirt	11 reviews
Hoot, Toot and Whistle Trail & Riverwalk Although short, the Hoot, Toot and Whistle Trail provides an enjoyable journey through peaceful woodlands on Wilmington's west end. As you might guess, the rail-trail gets its name from the former...	VT	2.3 mi	Dirt	4 reviews
Ware River Rail-Trail This unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...	MA	12 mi	Ballast, Dirt, Grass, Gravel	12 reviews
Appel Way Trail 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...	NH	1.3 mi	Asphalt	1 reviews
Ashburnham Rail Trail 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...	MA	1.3 mi	Dirt	1 reviews
Valley Trail The scenic Valley Trail spans 9 miles connecting Dover and Wilmington in southern Vermont along the Green Mountain National Forest. It provides a critical off-road pathway for bypassing State Route...	VT	9.1 mi	Asphalt, Dirt, Gravel	5 reviews
Bennington Rail Trail Running between downtown Bennington and the Northside Drive neighborhoods, the Bennington Rail Trail provides new opportunities for both recreation and active transportation. Following a former...	VT	1.65 mi	Asphalt, Crushed Stone, Gravel	0 reviews
Brookline Rail Trail The Brookline Rail Trail winds through the New Hampshire woods and passes by several small bodies of water, including the Potanipo Pond. The rail-trail has two segments, known as the Brookline Rail...	NH	4.5 mi	Crushed Stone, Gravel	0 reviews
Catamount Trail - Sections 1 and 2 The Catamount Trail offers 300 miles of backcountry skiing stretching across Vermont, from the Readsboro on the Massachusetts border, to North Troy near Canada. The trails are popular for winter...	VT	18.1 mi	Dirt	0 reviews
East Branch Trail (VT) The East Branch Trail is a 0.5-mile ungroomed, backcountry pathway built on a former logging railroad bed in southern Vermont's Windham County. The remote, heavily wooded trail lies just north of the...	VT	0.5 mi	Gravel	1 reviews
Henniker & Hopkinton Rail Trails The Henniker Rail Trail is an unpaved single-track path that follows a former rail corridor for 2.3 miles. The rail-trail picks up east of the former passenger station. Situated south of the Town of...	NH	6.7 mi	Dirt, Grass, Gravel, Sand	0 reviews
Keene Industrial Heritage Trail The Keene Industrial Trail links the county's Cheshire Rail-Trail in the city of Keene. The paved path is a 1-mile segment through downtown Keene, which passes among some of the city's old mill...	NH	1 mi	Asphalt	0 reviews
Merrimack River Greenway Trail The Merrimack River Greenway Trail (MRGT) will stretch from Boscawen southward through Concord to Pembroke, offering scenic views of the Merrimack River, the city and the surrounding landscapes. The...	NH	0.33 mi	Asphalt	0 reviews
Warner Rail Trail and Bagley Rail Trail The Warner Rail Trail and the Bagley Field Rail Trail are part of the Concord-Lake Sunapee Rail Trail, an eventual 34-mile rail-trail connecting Lake Sunapee and Concord, New Hampshire's state...	NH	1 mi	Crushed Stone, Gravel	0 reviews

Recent Trail Reviews

Sugar River Trail

amazing Trail

April, 2024 by nariipr

We had a great time on this trail, which was easy to navigate. It was our first outing this season since we acquired an ATV for my wife and we enjoyed spending time together while exploring nature. We encountered people walking their dogs and bikers along the way. The trail was well-maintained and clean. We made sure to slow down and say hello to everyone we met. We will definitely be back on this trail again!

Canalside Rail Trail

You can expand your ride…..

March, 2024 by basil1986

I love this trail! Rode it on 3/14/24 when weather was 62 degrees. This trail is short but can be expanded if you cross the metal bridge by the brewery and take the road to the left leading to the Fish Research Hatchery on the opposite side of the canal. If you meander through the little neighborhood on that side as well you can extend it further and get another view of the old mill complexes. I get 20 miles out of the ride. Bring a lunch there are picnic tables on both sides!

Ashuwillticook Rail Trail

Not ADA compliant

February, 2024 by ljt trike rider

It looked very nice from the parking area, but could not get through the barricades with a recumbent trike. Drove over an hour and gates were shut and would have had to lift trike over gates. Disgusted with Massachusetts and whomever designed the barricades. Has anyone heard of the ADA?

Accordion

Ashuwillticook Rail Trail

Great fall ride.

November, 2023 by cantabty

Excellent experience on this fresh paved trail. The scenery of the ponds and mountains in the distance was worth the trip.

Stevens Rail Trail

This was a great ride in both directions. After talking with Tim at the Warner Fall Foliage Festival we found out they were adding more trail on the other side of the bridge starting next week.

October, 2023 by imaginetravelsgd

This was a great ride in both directions. After talking with Tim at the Warner Fall Foliage Festival we found out they were adding more trail on the other side of the bridge starting next week.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

We found the Trail notTrail not as described

October, 2023 by luvaneezer

Cheshire Trail South. Rode north from State Line Circle toward Kenne. We are experienced road cyclists, now riding gravel bikes. We are looking for reasonably surfaced longer trails and hoped this would be one of them. Sadly, we found this trail to be rocky, rutted, with lots of roots, and uncleared blowdown. The vigilance required to remain upright made it difficult to enjoy the beauty all around. The suddenly occurring steep inclines to roads seemed borderline dangerous. If we lived closer it would be a great trail to walk with the dogs

Delaware and Hudson Rail-Trail

dog warning

September, 2023 by guamlee7

just walked the D & H trail from granville center to middle granville. really enjoyed the walk out toward middle granville but on the way back while walking through the farm (which was a delightful experience on the first trip through, seeing calves and cows) but then were charged by two pitties which attacked my dog and knocked me down. Luckily I had an umbrella and was able to get up and get away and down the trail. the dogs followed for a while but then returned to the farm. Too bad because was a very enjoyable walk until this. I just hope these two dogs dont really hurt someone....

Ashuelot Recreational Rail Trail

Still a lovely ride in spite of washouts

September, 2023 by nanlovell77

I would hate for people to avoid this lovely trail because of reports of the washouts. By using the trail map from this app or even Google maps you can easily find nearby roads that allow you to ride around the closed sections. We had a lovely 18.7 mi ride today and we’re able to keep cool because of lots of shade even though it got up to 90 degrees! They were repairing the bridge on the road to the Slate Covered Bridge, but they paused work to let us cross. It will be repaired very soon.

Monadnock Recreational Rail Trail

Pleasantly Surprised

September, 2023 by fyredown

Truly a nice ride this weekend. Packed surface, mixed terrain but nothing our Surly Ogre's couldn't handle. This was not a crowded trail but there were a spattering of walkers, bikers, dog walkers. Made you feel happy to be alive! Whoever is maintaining this trail - thank you!

Hillsborough Recreational Rail Trail

Bennington to Deering - compared with Jaffrey to Rindge

September, 2023 by fyredown

What will it take to get the Bennington to Deering Rail Trail suitable for bicycle??? It is a very difficult ride with even fat-tired riders because of the loose terrain. And then if you try to avoid it by riding the road, that is almost impossible also due to all the pitfalls and holes. This could be such an attraction.

I tried the Jaffrey to Rindge trail this weekend and there was NO COMPARISON! Fun, enjoyable ride while this one remains disappointing.

Please put this one on your list to help!!!

Northern Rail Trail

Danbury Country Store to Tewksbury Pond, Grafton

September, 2023 by chriscarney

Parked across from the Danbury County Store. Headed west towards Grafton. Only saw a coupe peopling using the trail this late Friday afternoon. Trail was smooth and dry even with rain the prior day.

Ashuwillticook Rail Trail

Good scenic ride

September, 2023 by richmedcraft

I rode the trail from Pittsfield to the end in North Adams and back on 8/5/23. The trail is paved and in good condition and restrooms at the Pittsfield trail head were clean and working fine. Nice scenery including lakes and the Berkshires- I was able to finally identify Mt Greylock after the morning clouds had dissipated. The grade is gentle and I was able to keep up a consistent pace for the ride.

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