Looking for the best trails around St Michaels?

Explore the best rated trails in St Michaels, MD, whether you're looking for an easy walking trail or a bike trail like the Smyrna-Clayton Bike Path and Hazlettville/North Shared-Use Path . With more than 95 trails covering 4459 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.

Holmes Run Trail

Tunnel under 395 finally re-open in April 2026!

May, 2026 by akbald01

This trail from Eisenhower is great and the tunnel under 395 is finally clean and reopened when I ran a longer out/back last month!

Great American Rail-Trail

Highly recommend this beautiful and well kept trail. Beautiful to ride along the trees and over the 2 epic ohiopyle bridges.

May, 2026 by sarahraekratz

Highly recommend this beautiful and well kept trail. Beautiful to ride along the trees and over the 2 epic ohiopyle bridges.

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.

Capital Crescent Trail

good trail

April, 2026 by aldo_desalvo

The part in the city is pretty boring. You get a nice tunnel and an old rail bridge. The surface is paved and has a few root issues. Most of the path is shaded. 5 stars

Arlington Loop

A Great route!

April, 2026 by dillon.marshall1999

I normally Ride to DC.. but this was a great Change of peace.. very scenic and the paths are paved nice and smooth.. lots of cyclist and people walking and running! Highly recommend!

Mount Vernon Trail

Easter weekend 2026. Saturday

April, 2026 by amy2paul

My husband, our two adult sons & I rode the trail yesterday. We hopped on at Unlimited Biking where we rented a bike for one son. Highly recommended. Employee was polite & had everything all re when we arrived. You can access the trail right there. We first rode north to Reagan Airport to watch the planes. That section was very busy! Lots of walker, dogs & bikes so be careful. Then we turned back south & had lunch before getting back on to ride to the end at George & Martha’s place. Much less crowded. Nice ride!

Washington and Old Dominion Railroad Regional Park (W&OD)

Ashland to purcerville

April, 2026 by aldo_desalvo

I did an up and back 35 miles. Great paved trail and. It many people at this end. Looking forward to riding the rest. I hate dc traffic

Woodrow Wilson Bridge Trail

I walked this trail a few times and absolutely love it, very peaceful.

March, 2026 by donand.robinson

I walked this trail a few times and absolutely love it, very peaceful.

Woodrow Wilson Bridge Trail

Great walk to end the month on. Beautiful scenery mostly flat.

March, 2026 by jerryproctor42

Great walk to end the month on. Beautiful scenery mostly flat.

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