Rockingham, VT Hiking Trails and Maps

622 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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Activities
Length
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42 Results
Activities
Length
Surfaces
Type

Ashuwillticook Rail Trail

13.9 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

Jonathan Daniels Trail

0.9 mi
State: NH
Crushed Stone

Keene Industrial Heritage Trail

1 mi
State: NH
Asphalt

Mascoma River Greenway

2.78 mi
State: NH
Asphalt, Gravel

Merrimack River Greenway Trail

0.33 mi
State: NH
Asphalt

Monadnock Recreational Rail Trail

7.5 mi
State: NH
Asphalt, Gravel

New Boston Rail Trail

3.9 mi
State: NH
Dirt

Northern Rail Trail

59 mi
State: NH
Cinder, Crushed Stone

West River Trail (Windham County)

16.1 mi
State: VT
Asphalt, Dirt, Gravel, Sand

Ashburnham Rail Trail

1.3 mi
State: MA
Dirt, Gravel

Ashuelot Recreational Rail Trail

21.4 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)

42.4 mi
State: NH
Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Common Pathway

5.5 mi
State: NH
Asphalt, Crushed Stone

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
Accordion

Hoosic River Greenway

2.5 mi
State: NY
Gravel

Lye Brook Falls Trail

2.2 mi
State: VT
Gravel

Mason Railroad Trail

6.7 mi
State: NH
Ballast, Gravel, Sand

North Central Pathway

11.2 mi
State: MA
Asphalt

Old Railroad Trail (NH)

2.7 mi
State: NH
Dirt

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

4.94 mi
State: NH
Asphalt, Crushed Stone, Dirt, Gravel

Brookline Rail Trail

4.5 mi
State: NH
Crushed Stone, Gravel

Concord-Lake Sunapee Rail Trail

5.65 mi
State: NH
Asphalt, Boardwalk, Crushed Stone, Dirt, Gravel

Granite Town Rail-Trail

3 mi
State: NH
Ballast, Cinder, Dirt, Grass, Gravel, Sand

Hillsborough Recreational Rail Trail

7.8 mi
State: NH
Crushed Stone, Dirt

Valley Trail

9.1 mi
State: VT
Asphalt, Dirt, Gravel

Ware River Rail-Trail

15 mi
State: MA
Ballast, Dirt, Grass, Gravel

Appel Way Trail

1.3 mi
State: NH
Asphalt

Bennington Rail Trail

1.65 mi
State: VT
Asphalt, Crushed Stone, Gravel

East Branch Trail (VT)

0.5 mi
State: VT
Gravel

Henniker & Hopkinton Rail Trails

6.7 mi
State: NH
Dirt, Grass, Gravel, Sand

Warner Rail Trail and Bagley Rail Trail

1 mi
State: NH
Crushed Stone, Gravel
Trail Image Trail Name States Length Surface Rating
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 the Hoosic...
MA 13.9 mi Asphalt
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
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
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
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
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
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
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
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
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
The Northern Rail Trail is New Hampshire’s longest rail-trail conversion, spanning 59 meticulously maintained miles, weaving along corn and hay fields, lakes, wetlands, and numerous historic sites,...
NH 59 mi Cinder, Crushed Stone
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
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, Gravel
Closure Notice: Due to flooding, the Ashuelot Recreational Rail Trail is closed from Sawyers Crossing Road heading southwest to Holbrook Ave (near Swanzey Lake Road) until further notice. Please see...
NH 21.4 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
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
The Cheshire Rail Trail connects Fitzwilliam, Troy, Keene, Westmoreland and Walpole. The 42.4-mile trail has a mostly gravel and dirt surface. The rail-trail plays host to a variety of uses,...
NH 42.4 mi Asphalt, Ballast, Cinder, Dirt, Gravel, Sand
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
The Delaware and Hudson Rail-Trail follows the flowing contours of the western Vermont countryside, rambling in and out of New York state, where there is a 4-mile gap. This border area is known as the...
NY, VT 25.8 mi Asphalt, Cinder, Dirt, Grass, Gravel
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
Harrisville and Hancock Rail Trails run for 6 miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris Center...
NH 6.1 mi Dirt
Accordion
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
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
The Mason Railroad Trail runs for nearly 7 miles from near the New Hampshire–Massachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...
NH 6.7 mi Ballast, Gravel, Sand
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
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
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
The Sugar River Trail runs for 9.5 miles between Claremont and Newport along the old Sugar River Railroad corridor. The 9.5-mile trail crosses its namesake river seven times—twice on covered...
NH 9.5 mi Ballast, Gravel, Sand
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
The Winnipesaukee River Trail runs for nearly 5 miles between the towns of Franklin and Tilton, nestled in the White Mountains of New Hampshire. About the Route The Winnipesaukee River Trail...
NH 4.94 mi Asphalt, Crushed Stone, Dirt, Gravel
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
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
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 found along...
NH 3 mi Ballast, Cinder, Dirt, Grass, Gravel, Sand
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
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
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
The Ware River Rail-Trail is an unpaved 15-mile rail-trail that stretches between Barre and Baldwinville, running through Hubbardston and Templeton along the way.  Following along the Burnshirt...
MA 15 mi Ballast, Dirt, Grass, Gravel
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
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
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
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
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
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

Recent Trail Reviews

Northern Rail Trail

Evening Ride

October, 2026 by pokeystache

Rode the trail from Lebanon till it got too cold. About 5 miles and then turned around and came back. Nice trail for a fat tire E bike. A few bumps but not too bad. Was very busy when we rode, but it was plenty wide enough that it did not cause a problem. Mostly shaded ride. Would have liked to go the entire distance.

Ashuwillticook Rail Trail

Great Trail

October, 2026 by pokeystache

We rode from Pittsfield to Adams and back. Very nice trail. 50% shaded. Ate lunch at AJ‘s at Adams. Nice restaurant in an old train depot. Limited parking at the beginning in Pittsfield. Start your ride at the next parking area to the north. Lots of lakes and rivers running next to the trail. Asphalt the entire length of the trail.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

The good: it’s being paved. The bad: signage through Keene

October, 2026 by pammer1959_tl

We hoped to do the entire trail by parking in the middle just south of Keene. The signage going through town was minimal and included being on the road quite a bit. The south side noted “road closed” because it’s being paved, but the road dead ended after 2 miles.

Disappointed is an understatement.

Accordion

Ashuwillticook Rail Trail

We rode the whole trail. It's smooth, scenic, and frequently bathrooms. The leaves are turning, such a beautiful trail. A must ride. It should be a Hall of Fame trail.

September, 2026 by sicnj2al

We rode the whole trail. It's smooth, scenic, and frequently bathrooms. The leaves are turning, such a beautiful trail. A must ride. It should be a Hall of Fame trail.

Ashuwillticook Rail Trail

Top Notch Trail

August, 2026 by trylondm

Biked end to end on a beautiful summer day. An absolutely beautiful paved trail with lots of water features to see - lakes to the south, river further north, and views of the mountains. Nice trailside pub in Adams and other eateries, including ice cream. Well-loved, with lots of walkers and skaters, as well as riders. Benches and picnic tables aplenty. One of the best trails I've had the privilege to ride. The only way it could possibly be better is if it was longer.

Correction to someone else's review: trail goes gently downhill south to north (not north to south) from Cheshire to Adams.

Northern Rail Trail

Could Use More Investment

August, 2026 by trylondm

I was involved with the development of this trail so my review is somewhat biased. The eastern half in Merrimack County (Danbury to Boscawen) is in beautiful shape (due to federal financing) with a nice stone dust surface. The western half (Grafton to Lebanon) is much more scenic but was done mostly by volunteers with some local funding so has a highly variable surface, great in areas and poor in others.

Highlights include the trail in Lebanon as it crisscrosses the Mascoma River, in Enfield where it runs several miles alongside Lake Mascoma and downtown, and all of Merrimack County thanks to its trail surface.

I dearly wanted to give it a 5-star rating but had to admit that it was a bit of a slog going through the central (and high point) towns of Grafton and Orange. Wish the state of New Hampshire would put some resources into this trail, which would truly make it a premiere destination and top-rated trail.

Catamount Trail - Sections 1 and 2

Catamount Trail Section 2

August, 2026 by awrootbeer

If you are a dedicated mountain biker than this would be a 5 star. Don't do this trail if you don't have a mountain bike or those fat tires. I was on a mountain bike, and my son had a regular bike. The beginning of the trail is easy and lovely. Once you connect with the trail (beautiful water views) the trail becomes mostly rock with some sand. Passed 1.8 miles the trail is impassable with our bikes. Somehow we made it out and back without falls or bike damage. I have biked other ski trails that were more compacted sand and dirt with some rock. This is not that kind of trail.

Sugar River Trail

Easy bike ride & beautiful nature

August, 2026 by sandal.brownell

We rode mountain bikes from Claremont to Newport. Nice easy ride. Only met a few others on the trail. We saw a blue heron, 2 hawks, blue jays, and beautiful mushrooms. There were spots on the trail that had a good bit of gnats. The covered bridges are wonderful.

Ashuwillticook Rail Trail

Well maintained trail with great views

August, 2026 by sebastianmhill

Awesome trail. Smooth surface and great views. Also lots of different places you can join the trail. We started a little further north to skip the more industrial part of the trail.

Ashuelot Recreational Rail Trail

Rough ride

July, 2026 by mroschella

Trail lacked any evidence of maintenance. Rode from Hinsdale to Winchester.

Delaware and Hudson Rail-Trail

Tale of 3 Trails

July, 2026 by trylondm

I did the entire trail, excepting the on-road portion in New York. Each section (the two in Vermont and the central part in New York) was quite different from the others, so I've broken my review into 3 parts.

The northern Vermont section (Poultney to Castleton) was in good shape and appears to get a lot of use, maybe 3 to 1 walkers to bikers. The surface of quarter inch gravel was not ideal, but enough has been brushed aside over the years that the ride was smooth and comfortable. It is well-maintained, mowed with no washouts or potholes, and just the right number of historical signs. It is generally well-shaded but probably the least scenic of the three sections.

The southern Vermont section (West Pawlet to West Rupert) was much more open and scenic, especially near Rupert, but Vermont's choice of quarter inch gravel surface is still generally in place so slows down the ride. A short detour to the general store in West Rupert for ice cream was a treat, as was a trail-side stream at the southern end to cool off in. The gentle slope made the northbound ride here more enjoyable than the southbound one. The trail was as well maintained as the northern portion. Ratio probably 4 to 1 bikers over walkers/joggers but fewer of both than the northern section.

The middle section in New York (West Pawlet to Middle Granville) was completely different. Parts of the surface were cinder (perfect for riding) while other parts were completely grass covered (and mowed) and as a result felt much like riding on someone's lawn - soft and slow. The scenery was less interesting, but the section in Granville was nice, with a park and B&B right on the trail. I didn't have time to explore the town, though. Despite the sunny Sunday, I saw few others using this part of the trail.

All in all, the trail was OK and has a lot of potential. With a better stone dust surface, I would have given it a 5-star. If the 4-mile break in New York between sections were completed, this would become a destination ride. With fall colors, it would be exceptional.

Harrisville and Hancock Rail Trails

Not for everyone!

July, 2026 by ktrenaud

2.5 stars. Entered the trail a the far western end on Hancock Rd. near Skatutakee Lake. Biked eastward for several miles. Mixed surface (dirt, cinder, sand & forest floor). This trail is rough and best suited for fat-tire or full-suspension mountain bikes. You could do it with a gravel bike but be ready for a very bumpy ride. Partially buried track ties and roots cover roughly over a 3rd of this segment of the trail. The swamps and brook are absolutely beautiful. There are a few benches for a peaceful stop. The trail has a gentle decline most of the way so be prepared for the uphill on the return trip. Mostly shaded so sunscreen isn't needed but bug spray might be a good idea if stopping for prolonged periods. The bridges are beautiful & well maintained. The signage is discreet & informative. This is a wonderful all season trail that I plan to return to in foliage season. It has a lot of potential but in its current condition it has a LONG way to go to become a destination that will attract tourists & generate $$$ for the local economy.

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