Looking for the best trails around Middletown?

Explore the best rated trails in Middletown, DE, whether you're looking for an easy walking trail or a bike trail like the Big Woods Trail and Elephant Swamp Trail . With more than 113 trails covering 465 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Michael N. Castle C&D Canal Trail

Michael N. Castle C & D Canal Trail

November, 2023 by thejake91739

Q: If I bike ride the short 1.8 mile Ben Cardin trail in Maryland, should I bother continuing on to Delaware's Michael N. Castle trail?
A: Most definitely! Why stop after just two miles?

Q: Is it as flat and easy as the Ben Cardin trail?
A: It's mostly long, flat and occasionally curves as it parallels the not perfectly straight canal, but there are three places where the trail leaves the canal and climbs up the side of the hill. There it's curvier and takes you through woodlands and by a marina.

Q: Are the hills strenuous?
A: For regular, fit bikers and old guys like me with a Swytch pedal assist system, no. For others I would say yes.

Q: How strenuous?
A: One is steep enough to warrant two switchbacks. I also encountered a middle aged couple at the top of one of the hills resting, recovering, and acting like, What have we gotten ourselves into? I also observed another young, fit woman jogging who had to stop halfway up the hill, bend over, and put her hands on her knees.

Q:Is it picturesque?
A: Yes, lots of interesting photo ops of bridges, the canal, birds, woodlands, salt marshes, watercraft, charming homes, and historical sites.

Q: So if I start in Maryland and reach 5th Street in Delaware City, that's where I turn around?
A: Technically, that's the end of the Castle Trail, but why stop there? Cross the road and continue for another mile or so along quiet Canal Road and the Delaware City Marina to old, historic Delaware City, Battery Park, and Delaware Bay! You'll regret it if you don't!

Q: Are there any rest stops or restrooms?
A: There are restrooms at South Lums Trailhead on the trail and at Battery Park. There are also benches consistently along the canal about every 250 yards!

Q: Is it safe? What are the trail users like?
A: The friendliest and most polite you could ever hope for!

Q: As a former educator, what grade would you give this trail?
A: An A, but not an easy A. You'll have to work hard to complete those six inclines (assuming you're traveling the entire distance and doing a round trip).

Ben Cardin C&D Canal Recreational Trail

Ben Cardin C & D Canal recreation Trail

November, 2023 by thejake91739

Officially, this Maryland trail is only 1.8 miles, perfect for the fine folks of Chesapeake City or tourists to take a stroll out to the state line with Delaware and back. In fact, as I sat on the deck of the Ship Watch Inn across the canal from the path's trailhead the evening before I rode it, I saw so many people doing just that.

The 3.6 miles round trip is perfect for walkers since it is flat, quiet, and picturesque. When I started my bike ride the next morning at sunrise, all I encountered were runners and friendly dog walkers.

However, those of us on bikes aren't going to stop after two miles, so be sure to combine this with the Delaware portion of the canal trail for an additional twelve miles.

AND . . . don't stop after those twelve miles. Since you've already gone that far, continue across 5th Street in Delaware City into the park and then bear right toward Canal Street to travel another mile or so to historical Delaware City, Battery Park, and Delaware Bay! Total round trip of thirty miles.

WARNING: If you decide to continue on to Delaware City, there are three hills on Delaware's Ben Cardin Trail. Thank goodness for my Swytch pedal assist!

Big Woods Trail

I took my family on this trail and with it being 3/4 paved and ending up at Hopewell furnace made for a lovely afternoon¡

October, 2023 by whdfshawn

I took my family on this trail and with it being 3/4 paved and ending up at Hopewell furnace made for a lovely afternoon¡

Accordion

Torrey C. Brown Rail Trail

Beautiful scenery, terrible surface

October, 2023 by timmunson

I was on this trail for the first and last time yesterday. My wife and I did a 21 mile round trip from the south end on a gorgeous day in October. This might be the prettiest trail I have ever seen. But the trail surface was a mixture of smooth, hardbacked dirt (nice) to something like a washboard. My wife sprained a muscle in her hand just holding on to the handlebars. I usually like to go back and finish a trail that I have only partially completed, but we won't be going back to this one.

Torrey C. Brown Rail Trail

Only did the northern 10 miles but...

October, 2023 by bestesbrau56_tl

I had never been on the Heritage Trail but I wanted to get a least 50 total miles in so I started at the parking lot near MM 16 and rode south. I crossed the border into MD and what a difference a State Line can make! I was not impressed at all with the ride on the Heritage but The Torrey was much more rural, did not have near the road crossings and you are for the most part riding beside a beautiful creek in a serene wooded environment instead of beside RR tracks in an environment that felt more industrial. I'll be back to complete the Southern end, for sure.

Rim Trail

Shady retreat

September, 2023 by weymouth.wellness

Beautiful easy walk under forest canopy. Cool shade on a warm sunny day.

Smyrna-Clayton Bike Path

Community Connector

September, 2023 by jmcginnis12

Actually a small network of multi-use trails, the Smyrna-Clayton Bike Path gives residents of both of these communities a great alternative to walking or biking along busy local roads.
The trail is comprised of two main branches, starting from Duck Creek Parkway on either side of the High School and Middle School campus. The northwest branch separates the high school from adjacent mini-storage facilities and a residential subdivision, while the northeast division follows a powerline that runs along a branch of Duck Creek and connects to the west side of Smyrna via a footbridge. Both branches of the trail wrap around the campus and converge just south of a small cow pasture. The trail continues southeast of here, crossing the creek on a footbridge and ending at the intersection of Routes 6 and 300.
In addition to giving local residents a chance to enjoy nature, the trail gives students at the high and middle schools a safe means to walk to and from school . Unfortunately, I noticed some minor deterioration on the footbridge northwest of the Route 6 and 300 intersection. People who are sensitive to loud noises should also be aware that the local fire company's emergency alert siren is just north of the junction between the northwest and northeast branches of the trail.

Monroe Township Bike Path

Easy, shady ride for a hot day!

September, 2023 by xerna17

We ride this trail a few times a year. Its very straight, smooth and mostly flat. Just a few very slight inclines. From Rt. 47 you ride a good distance before there are any road crossings. After that there are a few but only one or two that have a lot of traffic. Most of the trail goes through mature woodlands that give a lot of shade. My only complaint is that there don't seem to be any public bathrooms on the trail or at the trailheads. Otherwise, this is an easy, pretty trail.

Perkiomen Trail

bridge still out Labor Day 2023

September, 2023 by dpgnb6fnmv

Loved the trail, but the bridge being out added maybe 3/4 hilly mile on Rt. 29 to our bike ride. Hills also entering Green Lane Park, but the trail itself (not in the park) is very nice and mostly shady. Plenty if trailheads and parking. Meanders alongside the Perk. Creek.

Jones Falls Trail

Not a favorite

September, 2023 by shcavan_tl

This trail is poorly marked in numerous areas, not all areas are kept up, and there are many switchbacks. Just not a very enjoyable ride.

Torrey C. Brown Rail Trail

Rode on a weekday around 1 for a few hours. Not crowded and nice and peaceful.

September, 2023 by fizhman

Rode on a weekday around 1 for a few hours. Not crowded and nice and peaceful.

Easton Rails-to-Trails

Pleasant ride on a hot afternoon

August, 2023 by fisher1_tl

We just got back from a ride. Parked at the north end of the trail, and rode to the southern end and back. Took a detour through the new John F. Ford park, which was a nice surprise. Except for a few tree root speed bumps and some hickory nuts, the paved trail was in very good condition. More than half is shaded in the afternoon. Passed a few pedestrians, but had the trail mostly to ourselves. Not a trail to go speed riding, as there are frequent gates at road crossings.

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