Wayland, MA Horseback Riding Trails and Maps

1853 Reviews

Looking for the best Horseback Riding trails around Wayland?

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

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Activities
Length
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Type
32 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

60.3 mi
State: CT
Ballast, Crushed Stone, Dirt, Gravel

Blackstone River Greenway

31.6 mi
State: MA, RI
Asphalt, Boardwalk, Crushed Stone, Dirt

Border to Boston Trail

44.1 mi
State: MA
Asphalt, Boardwalk, Concrete, Crushed Stone, Dirt

Derry Rail Trail

3.6 mi
State: NH
Asphalt

Grand Trunk Trail

6.9 mi
State: MA
Crushed Stone, Dirt, Gravel

Haggetts Rail Trail

2 mi
State: MA
Crushed Stone, Dirt, Grass

Mass Central Rail Trail

64 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Medfield Rail Trail

1.3 mi
State: MA
Asphalt, Crushed Stone

Monadnock Recreational Rail Trail

7.5 mi
State: NH
Asphalt, Gravel

Nashua River Rail Trail

12.4 mi
State: MA, NH
Asphalt

New Boston Rail Trail

3.9 mi
State: NH
Dirt

New Hampshire Seacoast Greenway

8 mi
State: NH
Crushed Stone

Quinebaug Valley Rail Trail

5.7 mi
State: MA
Ballast, Cinder, Dirt, Grass

Washington Secondary Bike Path

19.2 mi
State: RI
Asphalt

Windham Rail Trail

4.3 mi
State: NH
Asphalt

Arkwright Riverwalk

0.8 mi
State: RI
Dirt, Woodchips

Bridle Trail

3 mi
State: MA
Dirt, Sand

Cheshire Rail Trail (Cheshire Branch Rail Trail)

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

Marblehead Rail-Trail

3.34 mi
State: MA
Asphalt, Dirt, Gravel, Sand

Mason Railroad Trail

6.7 mi
State: NH
Ballast, Gravel, Sand
Accordion

Potanipo Rail Trail (NH)

2.7 mi
State: NH
Crushed Stone, Gravel

Rockingham Recreational Rail Trail (Portsmouth Branch)

28 mi
State: NH
Crushed Stone, Dirt, Grass, Gravel, Sand

Southern New England Trunkline Trail

21.8 mi
State: MA
Asphalt, Ballast, Crushed Stone

Squannacook River Rail Trail

3.7 mi
State: MA
Crushed Stone

Brookline Rail Trail

4.5 mi
State: NH
Crushed Stone, Gravel

Granite Town Rail-Trail

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

Jay McLaren Memorial Trail

2 mi
State: MA
Dirt, Grass, Gravel

Martin H. Burns Wildlife Management Area Trail

3.4 mi
State: MA
Dirt, Gravel, Sand

Barker Road Trail

0.9 mi
State: MA
Dirt, Grass

Potanipo Rail Trail

3.4 mi
State: MA, NH
Crushed Stone, Gravel

Potanipo Rail Trail (MA)

1.7 mi
State: MA
Crushed Stone, Gravel
Trail Image Trail Name States Length Surface Rating
The Air Line State Park Trail winds 60.3 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is nearly...
CT 60.3 mi Ballast, Crushed Stone, Dirt, Gravel
Throughout history, the Blackstone River has been an important waterway, from its use by American Indians who fished its once-abundant salmon to its role as a major artery for the transportation of...
MA, RI 31.6 mi Asphalt, Boardwalk, Crushed Stone, Dirt
The Border to Boston Trail is a developing trail network that will stretch 70 miles between the New Hampshire border and Boston—providing a continuous route for a variety of non-motorized uses...
MA 44.1 mi Asphalt, Boardwalk, Concrete, Crushed Stone, Dirt
This exquisitely maintained 3.6-mile paved rail-trail slices through forested areas and wetlands for a wonderful experience in southern New Hampshire. About the Route Starting at the southern...
NH 3.6 mi Asphalt
The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. There are two longer sections of trail, in...
MA 6.9 mi Crushed Stone, Dirt, Gravel
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...
MA 2 mi Crushed Stone, Dirt, Grass
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. The Mass Central Rail Trail runs for 64 miles between...
MA 64 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
Built along the former Bay Colony Railroad line, the Medfield Rail Trail stretches between Ice House Road in the Town of Medfield to the town's border with Dover. Running primarily through woods, the...
MA 1.3 mi Asphalt, Crushed Stone
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 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...
MA, NH 12.4 mi Asphalt
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 New Hampshire Seacoast Greenway is an 8-mile rail-trail with a crushed-stone surface that stretches between Portsmouth and the North Hampton/Hampton border. Following a former Pan Am Railways...
NH 8 mi Crushed Stone
The Quinebaug Valley Rail Trail runs on the corridor once occupied by the Southbridge & Blackstone line of the Providence & Worcester Railroad, transforming a corridor once designed to link rural...
MA 5.7 mi Ballast, Cinder, Dirt, Grass
The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. About the Route The rail-trail, Rhode Island’s...
RI 19.2 mi Asphalt
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. The trail is 4.3 miles...
NH 4.3 mi Asphalt
The Arkwright Riverwalk, founded on a former rail bed purchased from Penn Central Railroad, is located in Coventry, a rural central Rhode Island town that was built around textile mills. The one-mile...
RI 0.8 mi Dirt, Woodchips
Marshfield's Bridle Trail follows a former railroad bed through a tree-lined corridor. It begins at the town's Dandelion Park and heads north. Its compacted dirt surface is best suited for walking,...
MA 3 mi Dirt, Sand
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 Marblehead Rail-Trail appears on maps as a Y resting on its side, connecting Marblehead and Salem in the north and the city limits of Swampscott in the west. The 3.34-mile trail knits together a...
MA 3.34 mi Asphalt, Dirt, Gravel, Sand
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
Accordion
Following the Nissitissit River through the woods, the Potanipo Rail Trail offers beautiful river views and launch sites for canoes or kayaks. Composed of two segments, the multi-use path is roughly...
NH 2.7 mi Crushed Stone, Gravel
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...
NH 18.3 mi Dirt, Sand
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 runs from Manchester, the state’s...
NH 28 mi Crushed Stone, Dirt, Grass, Gravel, Sand
The Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven Railroad's...
MA 21.8 mi Asphalt, Ballast, Crushed Stone
The Squannacook River Rail Trail is 3.7 miles long, from Depot St in the center of Townsend, MA, to the Bertozzi Wildlife Management Area in Groton, MA. The trail occupies the Greenville Branch of the...
MA 3.7 mi Crushed Stone
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
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
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...
MA 2 mi Dirt, Grass, Gravel
Note: This rail-trail is prone to frequent flooding and may be challenging to navigate at times. The rail trail through the Martin H. Burns Wildlife Management Area begins at the Massachusetts Bay...
MA 3.4 mi Dirt, Gravel, Sand
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...
MA 0.9 mi Dirt, Grass
The Potanipo Rail Trail is composed of three segments across New Hampshire and Massachusetts. Running through the woods along a former a rail corridor, the trail parallels the Nissitissit River for a...
MA, NH 3.4 mi Crushed Stone, Gravel
Paralleling the Nissitissit River as it runs through the woods, the Potanipo Rail Trail heads south towards Pepperell from the New Hampshire-Massachusetts state border. The Massachusetts section of...
MA 1.7 mi Crushed Stone, Gravel

Recent Trail Reviews

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Varied Terrain, MultiUse, Lovely. Birds!

April, 2026 by susanadeleedwards

Went north out of Keene on the trail, and was quickly in a lovely wooded area, then soon at a side trail to Stonewall Farm, where visitors are welcome to wander. The birds were singing happily! We did 6.5 miles out before turning around but there was plenty more trail to explore. If you are expecting a super flat trail and a packed surface this may not be your kind of fun. If you don’t mind dismounting for a rickety bridge, or adventuring on side trails, then check this trail Out ,

Groveland Community Trail

Some not so Good, Mostly very Good

April, 2026 by jim965

Starting at the Town Hall, the first half mile is on busy Route 113. There is a marked bike lane on both sides, but the sidewalk was not good for my recumbent trike and the road twists and turns, so visibility isn't great. I'll skip this part next time. At the half mile, Route 113 turns away and the trail goes along the river on a little traveled one way street. At a little over a mile, it's back on a two way street that has good visibility so it feels reasonably safe. As noted above, at 441 Main Street, the trail turns left onto a railroad roadbed, which is now a power line right of way, and continues southeast for almost two miles, with two road crossings. This is wide asphalt in excellent condition.

Although there are empty woods on the west side for much of the two miles, this is not a wilderness trail. I think there was at least one building in sight for the entire time.

In addition to parking at both ends mentioned above, there is parking at a National Grid facility at 452 Main Street, right at the head of the railroad trail.

Mayor James J. Fiorentini Bradford Rail Trail

Very Good, but too Short

April, 2026 by jim965

The trail is now wide asphalt in excellent condition, with clean, well groomed sides. Most of it is very close to the river, so, while foliage may obscure panoramic cross river views, it's still pleasant for a downtown trail.

Accordion

Hanover Branch Rail Trail

Easy parking at Circuit Street.

April, 2026 by nadineklink

Park at Circuit Street for very easy access to historic sites. There are many interesting things to see at this end including the 1829 West Hanover Cemetery and beautiful water features at this end. Recommended.

Topsfield Linear Common

Boxford piece short, but very good, Topsfield piece not good.

March, 2026 by jim965

First, be aware that the description is not accurate. The north end of this trail, from the dead end near I-95 to 2300 feet south of Pye Brook Road (PBR) is in Boxford, not Topsfield.

The portion north of PBR is a single rut, usable, but not great. From PBR south to the Boxford-Topsfield border it's a little over a yard wide, packed fine stone, not quite as firm as asphalt, but perfectly satisfactory for my trike. At the border, the trail becomes a single rough rocky track, barely usable and very uncomfortable on my trike. I can't comment further south, because I turned around.

Chelsea Greenway

trail

January, 2026 by haitaochen363

Good trail

Bruce Freeman Rail Trail

Great country ride, yet close to Urban life

November, 2025 by kleistikow

We’ve biked this many times. It quickly takes you from Lowell, with its National Park, etc to countryside and the center of small towns along smooth, paved, well-maintained trail. Nice to swim in Hart Pond, too, in season, on return trip to Lowell. Trail keeps getting better and better, great facilities along the way as trail is extended.

Washington Secondary Bike Path

Not a bad ride

October, 2025 by trainman1957

This trail needs open parking spaces! Most of the parking spots are blocked off!

East Bay Bike Path (RI)

Where is the bathroom if starting from Providence RI ?

October, 2025 by ningji

don't see bathroom in the parking lot

Salisbury Beach State Reservation Trail

large area lots to see.

October, 2025 by toddburrparts

Perfect place to ride for a beach day/ride. Explore the full state park and triple your mileage. A lot to see. And enjoy the ocean.

Monadnock Recreational Rail Trail

A little rough, but good trail.

October, 2025 by toddburrparts

Well, used multiple vehicle vehicles. Maintenance vehicle working on trail . Good views. Will ride again.

Deer Island Loop Trail

Neat little trail.

October, 2025 by chrismwy984

Nice short trail with beautiful views and an interesting history. If you’re biking, keep your mouth closed or you might ingest a fly in some spots.

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