We Know the Best Bike Trails on the Eastern Shore of Maryland!

It’s no secret that cycling is a big draw here on the Eastern Shore of Maryland! Our gently rolling, rural landscape makes for a perfect cycling destination. Go on a 2-wheeled adventure here and ride past pastoral family farms, the shimmering Chester River, and sprawling golden fields. No matter what trail you choose to follow, you’ll have an incredible cycling experience!

3 of the Best Bike Trails on the Eastern Shore of Maryland

The Rock Hall Ramble

If you’re up for a real challenge, the Rock Hall Ramble is for you! This extended ride is 50 miles long in true “sea to summit” fashion. On this bike trail, you’ll cover ground between Kent County and Rock Hall. Along the way, you’ll see all kinds of historical sites, top area restaurants, and, of course, beautiful views of the Eastern Shore itself. Be sure to check out Tolchester Marina and Rock Hall’s many fabulous restaurants during your ride.

The Historic County Loop

Another heart-pumping bike trail on the Eastern Shore of Maryland is the Historic County Loop. The total length of this loop is 81 miles, but there are plenty of shorter routes that feed into it. This challenging ride stretches past gorgeous Maryland countryside and offers incredible Chesapeake Bay views!

The Pump House Primer

Looking for a trail you can take that’s just a stone’s throw away from Brampton Inn? The Pump House Primer is a great option. While it spans 82 miles in total, this ride is well worth the extra time and effort it takes to complete. You’ll pedal all the way through Kent County and end up at the C and D Canal in Cecil County. Then, it’s time to make the journey back! Whether you choose to bike the entire 82 miles or just a portion of this Maryland bike trail, you’ll return to Brampton Inn with fond memories and a story to tell.

Local Tips and Hidden Gems for Cyclists

Looking for local knowledge before planning your Eastern Shore cycling getaway? Look no further than the folks at Brampton Inn! In the past, we have hosted multiple bicyclist groups, including the Carolina Tailwinds and Bike Vermont. Along the way, we learned to tailor our breakfast offerings to cyclists’ needs (we include potassium-packed bananas and an early start time) and hone our favorite biking spots to recommend.

We provide our guests with trail maps that include everything from easy, 5-mile rides to ambitious, 80-mile tours. One of our personal favorite routes takes you through winding back roads past St. Paul’s Church, through Rock Hall, and into the Eastern Neck Wildlife Refuge. Another one of our most popular rides is from Brampton Inn to Betterton Beach (where you can take a dip in the Chesapeake Bay, enjoy a waterfront lunch, then head back to your comfy bed at the inn). We encourage you to make an entire day of your cycling adventure!

Let Brampton Inn Be a Part of Your Eastern Shore Bike Tour

A blue bike awaits your next adventure at Brampton Inn

There’s no better place to blaze a trail than the Eastern Shore of Maryland. Instead of spending too much time searching for the best trails on your own, let Brampton Inn take care of the planning! In addition to providing you with spacious accommodations and complimentary breakfast, we can pack you a picnic for your ride or provide local lunch recommendations. We’re always happy to share our knowledge of the area so you don’t miss the best of Maryland’s Eastern Shore!

Ready for a ride you won’t soon forget? Check our availability today and start planning your trip!

If you liked reading about the best bike trails on the Eastern Shore of Maryland, you’ll love learning about hunting on the Eastern Shore and the best Chesapeake Bay scenic drives!

Dine in Style! 

If you are looking for a unique dining experience, we have two amazing dining-series this season!

Check out Dining Under the Stars with Chef Kurt Peter starting May 2!


Gourmet Diner Club with chef Jordan Lloyd starting May 23!

Dining and entertainment experiences to remember! See our Specials page.

Book Now

Want to be the first to know about specials and events? Sign Up Now