Kent Island is a great place to cycle. Easy to get to and beautiful scenery. We have two route suggestions: one for Casual Cyclists on the island’s two bike trails, and a route for Road Warriors who want some distance and speed away from the slower cyclists.  

The Ride

SHORT – 10 to 25 miles round trip | LONG – 40 miles round trip


Easy, depending on length | Flat, but constant peddling, plus any wind can make the road portion challenging

The Payoff

Island scenery includes water views, farmland, and woods


  • Plenty of parking – to chose your length
  • Changing scenery – water views, marshes, pine forests
  • Short route winds across entire island
  • Long route allows speed – challenging your peddling endurance
  • Lots of waterfront restaurants – most featuring seasonal Chesapeake Bay seafood


Kent Island has two asphalt-paved bike trails:

  • Cross Island Trail: 6.5 miles from Terrapin Nature Park to Long Point Park
  • South Trail: 7 miles from Matapeake State Park to Romancoke Pier

But those trails don’t connect. There’s a three-and-a-half-mile gap. We have a couple of recommendations if you want a longer ride. One for the casual rider and another for the road warrior — on different routes.

Kent Island Parking

Parking places are noted on the map above.

We begin the ride by parking near Kent Narrows. The reason is that you’ll end the day at the epicenter for crabs, oysters, fish tacos, and live music on the Eastern Shore.

The biggest lot is under the Route 50/310 Bridge. There are lots on both sides of Kent Narrows. No charge. This is also a good starting point for the Casual Route or Road Warrior Route. Both routes end here. 

The bike trail is next to all the parking lots.

From the Kent Narrows lot: if you want a very short ride, just do the Cross Island Trail. A little longer, add the South Island Trail.

Road Warriors take the Cross Island Trail to the long section of Kent Island and stay on the roads from there.

You’ll peddle across boardwalks over marshes, on an elevated path through pine forests, and finally through a park full of sports fields.


Romancoke Pier on Kent Island

The casual ride takes you on a nice tour of Kent Island turning around at Romancoke Fishing Pier with a great view of Eastern Bay.

Both trails independently may not give you a satisfying workout. However, if you combine the trails, and add a short jaunt along the local roads, you’ll have a flat and enjoyable longer ride.

The routes can be shortened based on time and energy. Pick a parking spot that works best for the length you want.

The asphalt cycling trails were repaved in 2019 and are awesome to ride on. However, they meander through the woods and can get busy, making it tough to get any speed going.

Kent Island's South Trail

The trail route has several boardwalk bridges over the marshes. Even on the new boardwalks, the wood makes a bumpy, rough ride on road bikes. You’ll be most comfortable riding a hybrid or comfort bike.

All routes are equally flat. The only hill is the Route 50 cross-over.

If you’re riding as a family with kids, they’ll enjoy the Cross Island Trail much more. It’s curvier. You go through woods and marshes and the scenery is constantly changing. There are also convenience stores along the way.

Cross Island Trail ends a half-mile past Love Point Road, in Terrapin Nature Park. It’s a pretty ride through forest. If that’s all you want, turnaround and peddle back to the parking lot. 

Cross Island bike trail crossing on Kent Island

If you want to ride on the South Island Trail, turn left here on Route 8 and ride along the wide shoulder for about 3.5 miles to the South Island Trail. It starts near Matapeake State Park.

Kent Island’s South Trail can be as curvy as the Cross Island Trail, but this section is more rural.

You’ll ride by the Kent Island airport, farm fields, a pretty golf course, and along several residential neighbors surrounded by wide spaces.

You’ll cross over several wooden bridges along both routes which can be slippery when wet.

Romancoke Pier on Kent Island, MD

When you’re ready, spin that bike around and head back the way you came.

The ride ends back at Kent Narrows where you’ll find family restaurants featuring Chesapeake Bay seafood. The bars usually have music on the weekends as long as the warm temps hold out.


Kent Point Marina on Kent Island

If you want a fast ride, it’s best to stick to the wide shoulders on the roads.

Keep in mind that flat is not necessarily easy. You have to peddle constantly. That’s easy for short rides. It’s tough on long rides and Kent Island can get breezy on the roads. You’ll find that this 40-mile ride provides a good workout. 

New signs have popped up to warn of busy sections, mainly in Severna Park. The trail typically clears out by mid-afternoon on weekends.

During the week, there’s a pattern. Early morning is the exercise crowd. In Mid-morning, the moms with strollers come out. Midday through mid-afternoon is fairly open. Kids and evening exercisers start coming out late afternoon and into the evening.

You’ll pass several popular restaurants, ice cream shops & pubs along the way, as well as convenience stores for reprovisioning. And there’s a bike shop on the trail in Severna Park.

The B&A Trail is a popular family ride and is an easy on-trail ride.

But, add the BWI Loop with its hills and you have a good exercise run. And because of that, the B&A attracts cycling groups, the kind that rides in formation. They're on their way to the BWI Loop.

Be aware that y'all have to share the space! Let people know when you're passing, keep to the speed limit, and it'll all be fine. 

Have a fun ride! Whichever route you pick.