Gloucester, MA Horseback Riding Trails and Maps

739 Reviews

Looking for the best Horseback Riding trails around Gloucester?

Find the top rated horseback riding trails in Gloucester, 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
Surfaces
Type
14 Results
Activities
Length
Surfaces
Type

Barker Road Trail

0.9 mi
State: MA
Dirt, Grass

Border to Boston Trail

10.7 mi
State: MA
Crushed Stone, Dirt

Bridle Trail

3 mi
State: MA
Dirt, Sand

Derry Rail Trail

3.6 mi
State: NH
Asphalt

Haggetts Rail Trail

2 mi
State: MA
Crushed Stone

Jay McLaren Memorial Trail

2 mi
State: MA
Dirt, Grass, Gravel

Marblehead Rail-Trail

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

Martin H. Burns Wildlife Management Area Trail

3.4 mi
State: MA
Dirt, Gravel, Sand

Mass Central Rail Trail

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

Nashua River Rail Trail

12.3 mi
State: MA, NH
Asphalt

Old Colony Nature Pathway

1.6 mi
State: MA
Dirt, Sand

Rockingham Recreational Rail Trail (Portsmouth Branch)

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

Windham Rail Trail

4.3 mi
State: NH
Asphalt
Trail Image Trail Name States Length Surface Rating
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 Border to Boston Trail connects the communities of West Peabody, Peabody, Danvers, Topsfield, and Boxford in northeastern Massachusetts. The long-term goal for the trail is to continue it north to...
MA 10.7 mi Crushed Stone, Dirt
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
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,...
NH 3.6 mi Asphalt
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
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
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 4-mile trail knits together a...
MA 4 mi Asphalt, Dirt, Gravel, Sand
The rail-trail through the Martin H. Burns Wildlife Management Area begins at the Massachusetts Bay Transportation Authority (MBTA) commuter rail station near downtown Newburyport, a coastal...
MA 3.4 mi Dirt, Gravel, Sand
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...
MA 38 mi Asphalt, Cinder, Crushed Stone, Dirt, 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 12.3 mi Asphalt
The Old Colony Nature Pathway is a short trail open on a former Old Colony Railroad corridor in Provincetown, a picturesque vacation destination at the tip of Cape Cod. While a longer portion of the...
MA 1.6 mi Dirt, Sand
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 begins in Manchester, the state’s...
NH 28.1 mi Crushed Stone, Dirt, Grass, Gravel, Sand
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...
NH 4.3 mi Asphalt

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Trails by activity

Windham Rail Trail

NH - 4.3 miles

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...

Mass Central Rail Trail

MA - 38 miles

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...

Haggetts Rail Trail

MA - 2 miles

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...

Derry Rail Trail

NH - 3.6 miles

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,...

Accordion

Marblehead Rail-Trail

MA - 4 miles

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 4-mile trail knits together a...

Border to Boston Trail

MA - 10.7 miles

The Border to Boston Trail connects the communities of West Peabody, Peabody, Danvers, Topsfield, and Boxford in northeastern Massachusetts. The long-term goal for the trail is to continue it north to...

Nashua River Rail Trail

MA,NH - 12.3 miles

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...

Barker Road Trail

MA - 0.9 miles

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...

Jay McLaren Memorial Trail

MA - 2 miles

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...

Mass Central Rail Trail

MA - 38 miles

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...

Marblehead Rail-Trail

MA - 4 miles

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 4-mile trail knits together a...

Accordion

Derry Rail Trail

NH - 3.6 miles

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,...

Haggetts Rail Trail

MA - 2 miles

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...

Rockingham Recreational Rail Trail (Portsmouth Branch)

NH - 28.1 miles

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...

Rockingham Recreational Rail Trail (Fremont Branch)

NH - 18.3 miles

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...

Old Colony Nature Pathway

MA - 1.6 miles

The Old Colony Nature Pathway is a short trail open on a former Old Colony Railroad corridor in Provincetown, a picturesque vacation destination at the tip of Cape Cod. While a longer portion of the...

Windham Rail Trail

NH - 4.3 miles

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...

Nashua River Rail Trail

MA,NH - 12.3 miles

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...

Bridle Trail

MA - 3 miles

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,...

Martin H. Burns Wildlife Management Area Trail

MA - 3.4 miles

The rail-trail through the Martin H. Burns Wildlife Management Area begins at the Massachusetts Bay Transportation Authority (MBTA) commuter rail station near downtown Newburyport, a coastal...

Border to Boston Trail

MA - 10.7 miles

The Border to Boston Trail connects the communities of West Peabody, Peabody, Danvers, Topsfield, and Boxford in northeastern Massachusetts. The long-term goal for the trail is to continue it north to...

Old Colony Nature Pathway

MA - 1.6 miles

The Old Colony Nature Pathway is a short trail open on a former Old Colony Railroad corridor in Provincetown, a picturesque vacation destination at the tip of Cape Cod. While a longer portion of the...

Derry Rail Trail

NH - 3.6 miles

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,...

Jay McLaren Memorial Trail

MA - 2 miles

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...

Martin H. Burns Wildlife Management Area Trail

MA - 3.4 miles

The rail-trail through the Martin H. Burns Wildlife Management Area begins at the Massachusetts Bay Transportation Authority (MBTA) commuter rail station near downtown Newburyport, a coastal...

Accordion

Marblehead Rail-Trail

MA - 4 miles

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 4-mile trail knits together a...

Windham Rail Trail

NH - 4.3 miles

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...

Border to Boston Trail

MA - 10.7 miles

The Border to Boston Trail connects the communities of West Peabody, Peabody, Danvers, Topsfield, and Boxford in northeastern Massachusetts. The long-term goal for the trail is to continue it north to...

Haggetts Rail Trail

MA - 2 miles

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...

Nashua River Rail Trail

MA,NH - 12.3 miles

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...

Mass Central Rail Trail

MA - 38 miles

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...

Bridle Trail

MA - 3 miles

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,...

Rockingham Recreational Rail Trail (Portsmouth Branch)

NH - 28.1 miles

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...

Barker Road Trail

MA - 0.9 miles

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...

Rockingham Recreational Rail Trail (Fremont Branch)

NH - 18.3 miles

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...

Recent Trail Reviews

Bay Colony Rail Trail

Bay Colony Rail Trail

October, 2019 by richardbrancato

A short but nice trail. Pretty much a straight shot with no hills. Similar to the World War II Veterans Memorial trail in Mansfield, but with no benches and in need of a bit more TLC. The trail is made of crushed stone and in one or two places it is a bit too loosely packed which can make steering your bike a bit challenging. Also, there is some encroaching brush on either side of the trail, but it is minor and does not get in the way too much. Not too busy. You can go back and forth and probably see 2 or 3 other bikers, walkers, etc. The parking lot is located across the street from where the trail begins. Overall, a nice trail if you are looking for a quick ride through the woods.

Whitney Spur Rail Trail

Whitney Spur Rail Trail

October, 2019 by richardbrancato

Very nice trail within Wompatuck State Park. There is free parking and plenty of it at the Cohasset MBTA station. The trail is listed as 1.6 miles, but it is actually longer than this as my TrailLink map was showing me as being off the trail but with still some trail to be had. The trail is nicely paved and alternates from the narrow and woodsy to the wide and open. On the day I went there were a few people on the trail with me such as walkers, joggers, fellow bikers, dog-walkers, moms with strollers, etc., but it was not crowded at all.

Assabet River Rail Trail

Hudson, Marlborough great for all riders

October, 2019 by bbuddy64

I've ridden this trail several times. Most recently today with my wife. Good workout if you start at Rte. 85 by McDonald's and push hard to Lincoln Street in Marlborough then head back and ride to the terminus in Hudson by Riverside Gun Club. Good 10.2 mile run that can be done in an hour after work.

Accordion

Minuteman Commuter Bikeway

Excellent Ride Through History

October, 2019 by llkamitchell

We rode from Bedford towards Boston and then returned via Lexington and Concord. Trail was an excellent pathway into Boston and had we had more time we would have continued into the city. Historically this trail is a gem waiting to be discovered.

Marblehead Rail-Trail

Great Trail

September, 2019 by dmcguire55

This trail has been well-maintained recently and there are so many great side-paths and conservation areas to explore. Good for walking, biking, dogs, and has a nice mix of dirt/gravel options.

Upper Charles Trail

Excellent Ride

September, 2019 by llkamitchell

We started in Milford and first rode to Holliston. The trail starts paved and then turns into a crushed stone but is well maintained throughout. Returning to Milford we then rode the other side of the trail which is paved throughout. Overall the trail is quite nice and a great option for two shorter rides or one long ride. Road crossings were easy and the traffic was quite kind. We have ridden in 33 states now and can easily give this trail a 9 out of 10. I will be posting a YouTube video of our ride using the username PedalPushin AK.

Assabet River Rail Trail

E Hudson lot next to Gun Club to Marlboro line

September, 2019 by mxi2002

Too many street crossings and too many hills. The ride back was a better. Next time, we'll park at Advanced Auto Parts, 157 Washington St to avoid all the street crossings in Hudson

Piscataquog Trail

trail markers

September, 2019 by janrogthebees

The only thing missing on this beautiful trail are markers. The Goffstown trail has markers starting at 0 mile on 1 side and on the other side it indicates 5.5 MI to the end, and then a marker every .5 mile EX: .5 MI, 1 MI., 1.5 MI. 2 MI. 2.5 MI. etc all the way to the end at 5.5 MI.

Reformatory Branch Trail

great experience

September, 2019 by kanishk

We have done this trail a few times as it connects nearby from the Minuteman commuter bike path. This is a great trail for a hybrid bike. You can connect from Lexington to Concord via this trail and then come back through the Minuteman Historic National Park trail. Overall, the trail is nice and goes through some ups and downs. We have done it as a family with kids and it was good. The views from the trail are also worthwhile.

Amesbury Riverwalk

loved this trail but wished there was better signage to make it easy to find it

August, 2019 by georgecat12

loved this trail but wished there was better signage to make it easy to find it

Derry Rail Trail

2019:08: Scenic, great ride!

August, 2019 by madasn

I always pair this trail with the Windham Rail Trail, I typically park at Hood Park in Derry and ride through to Salem. Parking is fine in the Hood lot. I don't think there's a porta-potty but there is one at the Windham lot.

I love this ride, it's near home so it's my default when I just want a quiet place to cruise. There are a few road crossings, all of which are clearly marked.

I find that the ride from Derry to Salem is a little bit easier than in the other direction. Neither direction is particularly challenging though, suitable for all. Can be a great leisurely trip or a workout, whatever you're looking for.

Until recently there weren't a lot of places to stop once you leave Derry center (save for a gas-station off-trail near the Windham trail-head). The Grind (fine coffee) has shops in Derry and just off the trail in Windham. The trail has been extended so that it reaches the Tuscan Kitchen (TK) in Salem. In the new section you can take a bridge to Dunkin' and get a coffee (the staff shared that a bike rack is coming in the future). If you want something more filling, you can leave your bike in the rack at the TK and visit the market or have an outdoor snack. Nice if you're looking for a break in the middle of your ride.

Notables:
- Scenic and peaceful; wetlands pop up throughout the ride offering sounds and views of nature
- You can take it easy or give yourself a workout
- Easy to plan for breaks and snacks with recent extension
- Trail is in good shape, some bumps (there's signage in the bumpiest areas and many random cracks have paint highlighting them)

Nashua River Rail Trail

2019/08: Scenic, well maintained, sport or family friendly

August, 2019 by madasn

First-timer on this trail, solo trip, I started in Nashua and traveled the full length, I took some time to explore off-road paths as well. Parking was great, a large lot with a porta-potty.

Overall, I really enjoyed this trail. I was there in August 19', I heard all the sounds of late summer in the woods and saw growing corn, ranches, peaceful wetlands, etc.

I don't generally stop for snacks on solos, but noted that there were places at several points along the trail to do so. Including an abutter's yard where they have cold drinks in a machine for $1 and seats to rest in. Thanks to that family/person, very cool of you!

I found that heading North to South was *slightly* easier. I didn't find anything particularly challenging on the paved trail but you could opt to coast a bit more in this direction. The trail is suitable for just about anyone to bike on. You can make it leisurely or push yourself and get a solid workout.

Notables:
- Each of the road crossings are clearly marked, helpful for new riders and/or kids
- A lot of things to look at; farmland, wetland, horses, river/damn
- Well maintained at the time of my visit (didn't experience problems with tree trunks, much of my ride was sitting back on the seat, arms at my side)

Definitely going back in the fall, will be worth a visit once the colors start to change

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