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 Springlawn Trail and Lincoln Drive Trail . With more than 114 trails covering 490 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

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.

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.

Accordion

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.

Big Woods Trail (PA)

needs work

November, 2024 by joelkring

This is to update a previous post. We recently rode the section that connects to the SRT and it is in need of major repairs. There are areas that were washed out and filled in with much larger stones. There were also places where there were deep loose stones. As a long time mountain bike rider, I was able to handle these obstacles, but I don't recommend this section of trail, except for walkers.

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