Chesapeake City Trails and Maps

1471 Reviews



Looking for the best trails around Chesapeake City?

Explore the best rated trails in Chesapeake City, MD, whether you're looking for an easy walking trail or a bike trail like the Ben Franklin Bridge and Delaware River Trail . With more than 142 trails covering 555 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

Kent Island South Trail

Kent Island South

May, 2026 by carrollb

I try to ride this trail 2-3 times a year. Had the trail to myself today except for a few people walking. The first 2 miles and the last 1 mile have a lot of raised places from the tree roots. Many places the asphalt is pushed up 2-3 inches. You have to keep your eyes on the asphalt in order to stand on the pedals or your back will be jarred really bad. At one point I heard a metal sound and after stopping found I did not have my rear bag fully zippered closed. The sound I heard was a tool being tossed out of my bag. This was a nice trail and it's a shame they don't mill down the raised places. Not sure if I will ride it again.

Heritage Rail Trail County Park

I'm a new super fan of rails to trails! Loved this ride. Especially Travelers Coffee and market. ¿¿¿¿¿¿

May, 2026 by jeaninejacildone

I'm a new super fan of rails to trails! Loved this ride. Especially Travelers Coffee and market. ¿¿¿¿¿¿

Monroe Township Bike Path

Nice paved ride

May, 2026 by littleredheadsmom

We love this trail. Almost 13 miles round trip.

Accordion

Smyrna-Clayton Bike Path

Nice Little Trail

May, 2026 by keithdel555

Easy to find once you arrive near the schools. It's a wonderful connector path for local residents to ride to the beautiful Smyrna school campus.

Capital City Trail

Trail non existent

May, 2026 by keithdel555

Mostly bike lanes along busy roads. The city is beautiful but I was disappointed that I could not find a trail along the water and lake. I even asked a State Trooper and they said that they were not aware of an actual trail.

Capital City Trail

where is the trail?

May, 2026 by keithdel555

I went down to Dover and followed the Google map and the trails map and could not find an actual trail. It appears that the trail is nothing but bike lanes on main roads. I asked a state trooper where the Jones River Trail was where there were signs pointing, and she had no idea what the Jones river was. Was very disappointed looking for the trails, but Dover is a beautiful town, especially in the legislative district.

Cynwyd Heritage Trail

Trail extended to Bala Station at City Avenue

April, 2026 by walking5

I rode this trail for the first time today (April 24, 2026). Contrary to the current map the trail does extend from the Cynwyd Station to the Bala Station at City Avenue. The extension looks quite new.

Schuylkill River Trail

Rode this trail so many times in my life and it never disappoints, a wonderful experience

January, 2026 by joerolland_tl

Rode this trail so many times in my life and it never disappoints, a wonderful experience

Perkiomen Trail

The perk

December, 2025 by twinbonz5

The hardest part is making it over springmount. I love the trail. I do it often. Made the 45 miles.

Enola Low Grade Trail

favorite trail

November, 2025 by kay.deitz

I start at Red Hill Road parking lot in Pequa and do the 20 mile round trip to Turkey Hill and back, it is flat, no potholes or surprises and glorious. Two bridges, 5 miles each way along the river, often a train, many groups of rock climbers on the weekend. Just glorious. If you want to add miles, going west is level and wooded. Some might say boring however I find it cool, refreshing and safe. My favorite trail!

Torrey C. Brown Rail Trail

very tough ride due to storm damage July ‘25

November, 2025 by kay.deitz

A lot of trail damage from storms in July 2025 makes for a very rough ride. Rough hard gravel, very bumpy ride. Could be dangerous if riding fast. My friends and I have moved to the Pa Heritage Rail Trail. NCR is more beautiful though rough. Would love to know if/when trail damage will be smoothed out. Got to be a budget for repair

Enola Low Grade Trail

Nice until mile 23…..

October, 2025 by acphillips1

Nice wide open relatively flat trail. It is after all a rail trail. After the 22 mile mark it turned pretty rough. Large gravel,mud…. I turned back….was hoping to take this to the end near gap. I do enjoy this rail trail. Well maintained nice country & river view for first several miles

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