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 Chester Valley Trail and Big Woods Trail. With more than 112 trails covering 451 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

Isaac Branch Greenway Trail

My local favorite

January, 2023 by fifty3tango

This is a great trail, well maintained, connects to other trails and full of wildlife. I have walked biked and run this trail for over ten years and it's never crowded. There is a small parking area on the southern end at the Rt 10 trail head with direct access to the trail. It's my go to place to walk my dogs or a bike ride without traffic.

Enola Low Grade Trail

Nice easy ride

December, 2022 by wadebusha

It's nice to be able to ride all the way through again but Too bad they had to build this hideous concrete and steel bridge though, instead of finding the person who burned the old one and hanging them from the trestle as an example.

Stockton Station Park Rail Trail

Great Park and Trail!

November, 2022 by eston.spain

Stockton Station Park offers peaceful and spacious amenities and an excellent paved trail. Although the length of the main trail is 0.36 miles long, there are paved sub-trails that connect the park features like ball diamonds, soccer pitch, and skateboard park and then reconnect to the main trail, allowing trail users greater than a half mile of paved walking surfaces. There are also benches and dog waste stations along the lighted trails.

Accordion

Jones Falls Trail

Beautiful Trail in the Heart of Baltimore

November, 2022 by tonybonta

Love this trail. Druid Hill Park is very scenic (and will only get better as the Druid Hill Reservoir project completes hopefully next year). It's great to be able to ride all the way down to the Baltimore Visitor Center and get something to eat in the inner harbor without having to deal with major traffic.

Two things to make note of. Be prepared for some fairly decent climbs heading south to north. And it's good to have the TrailLink app installed on your phone if you haven't done the trail before and don't know the turns. There are markings on the path and sidewalks, but they're starting to fade and in the fall, leaves cover a lot of them.

Schuylkill River Trail

people complain way too much

November, 2022 by powhiteboy

This trail was great!!! Transported my bike on the Amtrak bus from Philly to Reading and then rode the SRT back to Philly, staying the night at the Doberstein Campsite. Very enjoyable trip, highly recommend it.

Gwynns Falls Trail

Stream side Trail

November, 2022 by comebackcityus

I walked the trail for about 2 miles (4 miles round trip) starting at the trail head off of Washington Blvd near Carroll Park.

The pros are the scenery, beautiful trees and the stream views. The cons are you can hear I-95 at the beginning of trail and the isolation---few trail users.

Enola Low Grade Trail

Quarryville to Safe Harbor

October, 2022 by chboddy1963

Last Friday I rode my bike 28 miles I enjoyed it

Michael N. Castle C&D Canal Trail

Great trail

October, 2022 by tpnj

Road this trail with my wife 22 October 2022. Was very beautiful and temps were in the 60’s. Went from Delaware City to Chesapeake City and back for approximately 30 miles.

Enola Low Grade Trail

Worth the Wait

October, 2022 by zave smith

On Saturday, October 22nd, my wife and I, with a few friends, road this trail from Quarryville to the Safe Harbor bridge. With the reopening of both the Safe Harbor and Martic Forge bridges, this trail has become a delight. The trail is very flat, the surface is in excellent shape, and the scenery is wonderful. It was not very busy considering that it was a beautiful autumn day for riding.

It is also only an hour from our home near Philadelphia which means it will become part of our regular rotating weekend rides.

Perkiomen Trail

North end is horribly signed.

October, 2022 by

We started the trail at Green Lane. Can’t believe how poorly this trail is marked. Maps don’t help much either in this area.

Herring Run Trail

2.5 to 10

October, 2022 by redlocs_99

Parked at the st francis school along the street one Sunday afternoon. Soccer day so parking was limited. Noted the lake nearby, across the street and was pleased to see a walking, biking and car (no cars allowed) path going around the lake for 1.5mi. Nice warm up. All sun, no shade, nice mix of bikers joggers walkers. But not too crowded. Returned to the head of the herring trail -far side of the soccer fields, immediately descends and hooks right. Hard right and you ride along the soccer fields and the right side of the creek. Left, you go over a small wooden bridge, and are on the left side of the creek. Average sized path, tight/blind corners at first but then is open enough to see in oncoming foot/bike traffic. Two major street crossings and a handful of minor one, it’s a fairly olead r 2.5 ni all paved mainly flat path that’s a loop

Chester Valley Trail

fun outing!

October, 2022 by patticampbell4

We’ve ridden short distances on this trail toward King of Prussia ( ride to K of P Town Center and eat outside at one of the many restaurants) but last week was Our first excursion towards Exton. There are lots of road crossings, and road noise from Route 202, but it was so pretty! We’ll maintained, plenty of benches to sit and have a drink. I thought it was a great ride. Other riders were friendly and there were walkers too. I highly recommend it!

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