Weston, MA Horseback Riding Trails and Maps

1893 Reviews

Looking for the best Horseback Riding trails around Weston?

Find the top rated horseback riding trails in Weston, 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
31 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

Mass Central Rail Trail

72.2 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

9.6 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

Potanipo Rail Trail (NH)

2.7 mi
State: NH
Crushed Stone, Gravel
Accordion

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 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 72.2 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 9.6-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 9.6 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
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
Accordion
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

East Bay Bike Path (RI)

beautiful ride

October, 2026 by chleary11

Started at veterans memorial parking lot as per many reviewer’s suggestions. What a great ride down to Bristol! A few things to note—there are a lot of street crossings but most are not busy. There were only 2 where I had to wait and push the cross signal. There were no bathrooms on the trail but you could stop in barrington or Warren if needed. There is a bathroom at the end of the trail in Bristol. Bristol is a lovely town to stop and walk around. Colt park is a good option also, but I didn’t do the 4 mile extension. I just rode into the park and out. It was a great fall ride!

Narrow-Gauge Rail-Trail

Parking info

October, 2026 by jbhostage266

The trail map indicates there is parking at the crossing with Pine Hill Road, but it is not really designed as a parking area. There is room for one or two cars to pull off the road. There is a real parking lot with room for maybe a dozen cars at Sweetwater Avenue, the location of the Fawn Lake Conservation Area.

Air Line State Park Trail

Beware

October, 2026 by 8jp5rr55yf

So I started this trail in Portland, Connecticut, and about 3 to 4 miles into it. It stops at a marsh river area. There is no sign to tell you that it does or what detour to take. You would have to get on the main road to avoid this section. And the way people drive on that road I wouldn’t trust it. From what I heard, they were supposed to build a bridge over this section but said they were waiting for EPA to be involved which was years ago so I would highly recommend that you start in East Hampton for continued access.

Accordion

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.

Tri-Community Greenway

Great in section, too many road crossings

September, 2026 by robertbgates13

This trail has several wonderful, delightful, beautiful sections. But there are a few too many street crossings, and the signs could be better for those who are new.

Rockingham Recreational Rail Trail (Portsmouth Branch)

beautiful forrests but lots of rocks

September, 2026 by 3monroe3

This trail is very peaceful and few others are using it. The trail has a lot of protruding rocks, uneven surfaces and branches on it. Best for hiking or if you are going to bike, like we did, just go slowly and enjoy the surroundings

Twin Cities Rail Trail

A few too many crossings at the Leominster end, but its a fine trail. Last quarter mile or so on the Fitchburg end isnt so much a trail as it is street riding.

September, 2026 by cedwardpierce923

A few too many crossings at the Leominster end, but its a fine trail. Last quarter mile or so on the Fitchburg end isnt so much a trail as it is street riding.

Washington Secondary Bike Path

Lovely lovely trail!

August, 2026 by amygallatin

We rode from the parking lot at Quidnick St. in West Warwick to the abrupt end of the trail in Summit (Coventry), about 20 mi round trip. Pavement in very good shape. Trail is shaded for much of the way making for a pleasant ride. Lots of views of ponds, lakes, reservoirs and streams. Significant uphill climb to the end of the trail in Coventry but a screaming downhill for much of the way back. We plan to return in the fall, foliage will doubtless be stunning. Trail is paved throughout, and the western part of the trail is shared with equestrians, although sadly we did not see any.

Pine Tree Brook Path

Good for little kids Mountain Biking

August, 2026 by andrew.magruder

My 6 and 9 year old grandsons rode the 2.5 round trip with maybe 100 feet of walking their 20” mt bikes over rough spots and a couple of logs. The trail is 95% shaded. We parked on Breck Rd and crossed Thacher Rd to the trailhead. Lafayette Rd has a large circle at its end by Pope’s Pond that you clearly can park at.

Air Line State Park Trail

geminird review misleading

August, 2026 by atclaw

This rider was going Northeast from Willimantic towards Hampton NOT Southwest from Willimantic to East Hampton. Having ridden both stretches I can say his description is completely wrong about the gorgeous and open riding Southeastern route and not completely wrong but somewhat overly harsh about his route which can get iffy for stretches.

Charles River Bike Path

Skip the Western End

August, 2026 by trylondm

This trail gets better and better as you get closer to downtown Boston. It also gets more crowded. Very scenic with lots of views of the river and such, but as always in Boston, there will be detours here and there due to construction. Probably gets better the more times you ride it and get to know its quirks. Not a trail if you are looking for speedy biking due to the number of pedestrians, runners, and other folks - it is certainly well-loved by Bostonians!

Western end beyond the Galen Bridge to Waltham gets squirrelly with odd and sometimes confusing routing and signage - not recommended unless you've got all day like I did.

Nashua River Rail Trail

Still a 5 Star Trail

August, 2026 by trylondm

Yes, the comments about all the root heaves along the paved trail are true, but otherwise a very attractive ride. The TrailLink description is very accurate. Might be special in foliage season.

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Accordion

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