Cycling Routes & Maps Around the Chesapeake Bay

The Chesapeake Bay region has an abundance of fun, beautiful cycling routes for all levels. Below are maps and information about assorted routes.

From casual riders who feel fine to cruise at 10 mph to hard-core, all-matching power peddlers who find it hard to go under 20 mph, we have a Chesapeake Bay cycling ride for you.

A lot of people are new — or returning — to cycling. We want to help you get out on your bike.

Some routes are on bike paths, others are on Maryland’s country highways with wide shoulders.

We’ll have a few routes on county lanes or highway sections with no shoulders, but we’ll let you know. Generally, we don’t like to ride on roads with a lot of vehicles either.

Eastern Shore Cycling

Maryland’s Eastern Shore is flat. Very flat.

(Photo by Virginia Tourism Corporation,

A highway overpass is big elevation on the Eastern Shore. Flat is easy for short distances, but challenging on long distances. You never get a break from peddling.

Our routes tend to go by water, around water, to water. It’s beautiful.

Cycling on Hooper Island
Hooper Island

The downside to Eastern Shore cycling is that there’s not much stopping the wind off the water. On breezy days that’s just an extra challenge, like riding at higher gear.

However, these rides have a big pay-off. Gorgeous views, great workout for all levels and a cool small-town to start-and-end your ride.

Click the boxes to see the bike routes.

C&D Bike Trail

This beautiful 30-mile (roundtrip) trail follows the Chesapeake and Delaware Canal from Maryland’s Chesapeake City to Delaware’s Delaware City. Both are historic towns. The trail is easy and generally flat because it’s along the canal most of the way. The only hills are where the trail detours around streams or wash-outs in the trail.

Kent Island

Romancoke Pier on Kent Island, MD

Kent Island has a couple bike trails that can be combined with a bit of a wide-highway-shoulder ride to make a 30-mile round trip. Or stay on just the trails and choose your 10-to-15 mile ride (roundtrip) on asphalt bike trails that meander past water and through woods.

Oxford Loop

Cyclists on Oxford ferry in Maryland

The Oxford Loop from St. Michaels (or Easton) is a 30-mile ride along wide highway shoulders that not only takes you to the adorable village of Oxford. It includes a ferry-ride across the Tred Avon River at Oxford. There is a short section without shoulders when you get off the ferry at Bellevue.

Rock Hall to Eastern Neck Island

Pier at Bogles Wharf on Eastern Neck Island

The approx. 20-mile ride to Eastern Neck Island is flat and easy. You ride along scenic farm fields backed up to water, as well as wetlands, over a small bridge and onto the Eastern Neck Island Wildlife Refuge. It’s on a country highway with no shoulders.

St. Michaels to Neavitt Landing

Cycling to Neavitt Landing

The ride to Neavitt Landing is short, about 20 miles and totally flat. You roll through a couple villages and past farm fields with an occasional water view. But you end at the landing, a marina for working watermen. Easy ride ending at a gorgeous view; what’s not to like?

St. Michaels to Tilghman Island

Tilghman Island painting on side of building

Tilghman Island is a flat 50-mile route on a wide highway shoulder, but it’s not easy. There’s no break in peddling and it can be breezy. However, Tilghman Island is a very cool trade-off and a great place for a lunch or just a long break.

Western Shore Cycling

Maryland’s Western Shore is hilly.

Main Street in Annapolis going downhill to the harbor.
Main Street in Annapolis going downhill to the harbor.

The flattest trails you can find are rails-to-trails routes, former railroad routes. Hills are generally limited to a three-percent climb because that’s what trains could climb. But as time goes by, overpasses are added or occassionally the route veers away from the former train route up a hill.

But here’s the upside to cycling hills — for every up, you get a peddling break on the way down. The rollercoaster effect can be fun.

Because the Eastern Shore is easier, we have a few more routes over there. However, we’re working more on the Western-side of the Chesapeake Bay Bridge.

B&A Bike Trail

B&A Bike Trail

The B&A bike trail is a asphalt-paved rails-to-trails route. It’s 40-miles round-trip from the Annapolis trailhead and back. The BWI Loop at the far end of the trail adds another 10-miles and a few hills. Here’s a breakdown of the routes. It’s a scenic, but busy trail, especially through Severna Park. BWI Loop is less crowded.

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