Middletown, DE Horseback Riding Trails and Maps

1238 Reviews

Looking for the best Horseback Riding trails around Middletown?

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

Elephant Swamp Trail

5.1 mi
State: NJ
Crushed Stone, Dirt, Gravel, Woodchips

Michael N. Castle C&D Canal Trail

12.4 mi
State: DE
Asphalt

Perkiomen Trail

20.6 mi
State: PA
Asphalt, Crushed Stone

Rim Trail

2.2 mi
State: PA
Crushed Stone

Springlawn Trail

2.1 mi
State: PA
Dirt, Gravel

Struble Trail

2.6 mi
State: PA
Asphalt

Torrey C. Brown Rail Trail

19.9 mi
State: MD
Crushed Stone, Dirt

Wissahickon Valley Park Trail System

8.5 mi
State: PA
Asphalt, Dirt, Gravel

Big Woods Trail (PA)

3 mi
State: PA
Crushed Stone

Buena Borough Bike Path

1.9 mi
State: NJ
Asphalt

Little Jersey Trail

8.1 mi
State: DE
Crushed Stone, Dirt

MA & PA Heritage Trail

5.1 mi
State: MD
Boardwalk, Crushed Stone, Dirt

PennDel Trail

5.4 mi
State: DE, PA
Asphalt, Dirt, Gravel

Lower Susquehanna Heritage Greenway Trail

2.5 mi
State: MD
Crushed Stone
Trail Image Trail Name States Length Surface Rating
Overview Walking along the Elephant Swamp Trail, it’s easy to see where it picked up the swamp part of its name. As for the rest, legend has it that in the late 1800s, an elephant got loose in the...
NJ 5.1 mi Crushed Stone, Dirt, Gravel, Woodchips
Overview The Michael N. Castle C&D Canal Trail offers a scenic 12.4-mile route along the north shore of the Chesa­peake and Delaware Canal in northern Delaware. The popular trail is named after the...
DE 12.4 mi Asphalt
Closure Notice: Northern portions of the trail are closed due to flooding. Stay up to date on this closure by visiting the Montgomery County page.  Overview The Perkiomen Trail spans 20.6 miles...
PA 20.6 mi Asphalt, Crushed Stone
The Rim Trail offers a 2.2-mile route in Hibernia County Park, following a former railroad bed along the West Branch Branywine Creek. This southeastern Pennsylvania excursion is one of a handful of...
PA 2.2 mi Crushed Stone
The Springlawn Trail travels on what was once Springlawn Road, connecting Chesterville Road (Rt. 841) and Strickersville Road. The 2-mile trail is comprised of dirt and gravel and makes for a good...
PA 2.1 mi Dirt, Gravel
The Chester County Parks & Recreation Department opened this trail in 1979 on part of a former Pennsylvania Railroad right-of-way. Today the 2.6-mile trail attracts more than 125,000 visitors each...
PA 2.6 mi Asphalt
Overview The Torrey C. Brown Rail Trail is a popular destination for outdoor enthusiasts because of its proximity to populous Baltimore and its relatively flat course, which winds along river...
MD 19.9 mi Crushed Stone, Dirt
Overview Visitors to northwestern Philadelphia can acquaint themselves with the parks that surround Wissahickon Creek on a 8.5-mile system of multiuse trails. In the north, the Wissahickon Trail...
PA 8.5 mi Asphalt, Dirt, Gravel
Envisioned as a multi-use trail that will eventually connect the Thun Trail section of the Schuylkill River Trail in Union Township in southeast Berks County to the towns of Elverson and St. Peters in...
PA 3 mi Crushed Stone
This bike path begins along Southwest Boulevard at Harding Highway (US 40). It continues alongside the boulevard, then crosses Central Avenue and slipping into Bruno Melini Memorial Park, Buena’s...
NJ 1.9 mi Asphalt
The Little Jersey Trail loops through Lums Pond State Park on a wide, packed earth surface that accommodates hikers, cyclists and equestrians. The trail is the longer of two loops; the Swamp Forest...
DE 8.1 mi Crushed Stone, Dirt
The MA & PA Heritage Trail is not your typical rail-trail. Named for the Maryland and Pennsylvania Railroad, which chugged through the Harford County countryside for the first half of the 20th...
MD 5.1 mi Boardwalk, Crushed Stone, Dirt
Also known as the Creek Road Trail from its origin road in Delaware, the PennDel Trail extends north from a connection with the Pomeroy and Newark Rail Trail in White Clay Creek State Park. The scenic...
DE, PA 5.4 mi Asphalt, Dirt, Gravel
Maryland's Susquehanna State Park is recognized for challenging hiking and biking trails, camping facilities, rock outcroppings, boating, a museum and restored historical sites. But none of these...
MD 2.5 mi Crushed Stone

Recent Trail Reviews

Perkiomen Trail

A delight

April, 2025 by wlexieart

Aesthetic wise a very pleasing experience, everything a trail could have, parks, picnic areas, woods, rural roads, bridges, town, connector trails. Mostly flat with one incline for good measure. Long or short rides . A true delight, a fave!

Gwynns Falls Trail

Decidedly mixed experience, probably won't repeat

April, 2025 by julie.lundquist

Rode south from Inner Harbor to MedStar Harbor Hospital, a decidedly mixed experience. The "urban" part is tricky, not well-signed, and lots of crumbly asphalt and broken glass. The spot where the Middle Branch Trail/E Coast Greenway hits Russell St (south of Top Golf, just north of the Wheelabrator) is also a spot for people to gather, didn't feel very safe. (It was neat to see Gwynnda the Good Wheel of the West near there, however.) The "Westport" section of the trail feels very exposed: deserted industrial with occasional cars with opaque windows...once you arrive to the Middle Branch Park, the trail is more park-like but not well-populated even on a beautiful day and the trail is not in great condition. Pretty views of Baltimore from the coast. If you're departing from the inner harbor, would recommend just biking out to Fort McHenry instead - a bit more traffic but feels significantly safer and much nicer.

Jones Falls Trail

Surprisingly well-maintained for Baltimore City. Northern half is very hilly.

April, 2025 by tnbpptw5x7

It’s in great shape compared to some of the city streets, and is somewhat well-marked. I used the map on the TrailLink app to make sure I didn’t make a wrong turn, and would recommend the same to other riders. Sometimes you have to share a sidewalk or street, but when you do they’ve been widened for it. North of Falls Road, there are several sets of switchbacks and several hills.

Accordion

Enola Low Grade Trail

Kinda boring at times, but great for long rides

March, 2025 by tnbpptw5x7

The trail is incredibly straight, so it can seem boring at times, but that also makes long rides easy since you can just go without having to slow down for roads or anything. Eden and Bart townships have done work on improving their segments, and the whole trail, even where it says “unimproved,” is perfectly rideable until Atglen, where it does deteriorate a bit. Overall great trail.

MA & PA Heritage Trail

Crowded but manageable

March, 2025 by tnbpptw5x7

I often had to slow down for pedestrians on a weekend in February. Has some brief but aggressive climbs. Excited for the final piece to open soon.

Torrey C. Brown Rail Trail

Don’t go in January

March, 2025 by tnbpptw5x7

I tried to do this trail in segments in January. The snow melts way slower on the trail than in other unplowed places. I also think the grades in the northern parts are tough.

Brandywine Creek Path

Best City Park

March, 2025 by chris.tijerino

The Brandywine is the perfect city park. It connects most every neighborhood along the Brandywine river. Plenty of space for joggers, kids, dogs and folks who use walking aids. Scenic, clean and minimal noise pollution.

MA & PA Heritage Trail

Getting longer

March, 2025 by finman57

The map shows the trail stopping at Main Street in Bel Air. Another mile has been added to that. It’s been there a couple of years and now they are working on a new section. When done this will connect the two sections that are existing. While this is the closest trail to me I seldom ride it because of two things. 1 is it does not really follow the old rail bed the whole time. Because of this it has some major hills. 2 is that it is to crowded for me. All personal opinions.

Isaac Branch Greenway Trail

This is a really nice trail for a quick ride on any kind of bike. Really enjoyed it today wish it was longer.

February, 2025 by reram2224

This is a really nice trail for a quick ride on any kind of bike. Really enjoyed it today wish it was longer.

Cooper River Trail

Someone Special took me here summer of 2024 and it was a nice walk around the lake! Was going to come back in the spring unfortunately without that special someone ¿

January, 2025 by tcdowns72

Someone Special took me here summer of 2024 and it was a nice walk around the lake! Was going to come back in the spring unfortunately without that special someone ¿

Maurice River Bikeway Trail

This is a good place to hike all the trails for a couple hours! Great views!

January, 2025 by tcdowns72

This is a good place to hike all the trails for a couple hours! Great views!

Cross Island Trail

Cross Island extended

November, 2024 by smerchant1120

I frequently ride the Cross Island Trail. You can extend your ride starting at the Royal Farms. Continue on Sadler Rd when it ends make a left on Chester River Beach Rd then right on VFW Ave. At the Quality Inn make a left onto Winchester Creek Rd. Then right onto Hissey Rd and then left back onto Winchester Creek Road. Stop at Nesbit Rd. The roads are not busy and will add 4 more miles to your round trip.

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