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

kids biking on trail

Are you ready for an adventure? We’ll help guide the way with local tips on some of the most popular bike trails on Maryland’s Eastern Shore. A bike ride here is more than just a great way to get some exercise. It’s a fantastic opportunity to visit historical sites, admire nature, and enjoy breathtaking views of the Chesapeake Bay. Read on to find out which bike trail is right for you, and book one of our exceptional vacation rentals nearby so that you can unwind in comfort after your journeys.

Explore Maryland’s Eastern Shore on These Bike Trails

Some of the best bike trails in the area run throughout Talbot County. Here’s an overview of each one:

School Days

First on the list is the School Days bike trail. This scenic route begins in Easton, MD, and leads you to various historical sites, including a schoolhouse from 1865, a Civil War cemetery, and an environmental center where people have spotted over 200 species of birds. If you enjoy birdwatching, this is the bike trail for you. Bring binoculars to see if you can catch glimpses of bald eagles, herons, egrets, and more!

Distance: 28.3 miles

Starting Point: Rails to Trails parking lot in Easton

Highlights: Little Red Schoolhouse, Unionville Cemetery, and the Pickering Creek Audubon Center

Joust Maryland

Did you know that the state sport of Maryland is jousting? That’s actually where this trail got its name! Start your journey in Wye Mills and don’t forget to stop at the St. Joseph’s Church along the way. It’s the venue for the annual Jousting Tournament and Horse Show, which has been running for over 150 years!

Distance: 26.7 miles

Starting Point: Wye Oak State Park in Wye Mills

Highlights: Wye Oak State Park, St. Joseph’s Church, and Wye Landing

Talbot Farmland

Another fantastic option is the Talbot Farmland trail with gorgeous views and wide-open spaces in an agricultural atmosphere. There are a few side trails to explore which take you to Covey’s Landing, Reeses Landing, or Kingston Landing, all of which feature views of the Choptank River. The bridge at King’s Creek is also a lovely area for birdwatching!

Distance: 27.6 miles

Starting Point: Rails to Trails parking lot in Easton

Highlights: Choptank River and the King’s Creek bridge

Chesapeake Views

Chesapeake Views is a down-and-back trail that runs through Claiborne, McDaniel, Wittman, Sherwood, and Tilghman. It’s a longer trail than the others, but the beauty of the Chesapeake Bay waterfront makes it more than worthwhile.

Distance: 38.2

Starting Point: Claiborne Landing in Claiborne

Highlights: Charming small towns and waterfront views

Oxford/St. Michaels

The Oxford/St. Michaels bike trail is known as one of the top bike trails in the region, and even the country! Start in the beautiful town of St. Michaels and see a variety of historic communities along the way, including Oxford, Royal Oak, and Easton. Keep in mind that this trail requires a ferry ride which is only available from the spring to the fall.

Distance: 29.6 miles

Starting Point: Chesapeake Maritime Museum in St. Michaels

Highlights: Waterfront views, charming communities, and the Oxford Bellevue Ferry

Cemetery Quest

Last but not least is Cemetery Quest, which begins in Easton and runs for a total of 28.1 miles in a scenic loop. The “Quest” is to find all of the cemeteries along the path. Will you find them all?

Distance: 28.1 miles

Starting Point: Rails to Trails parking lot in Easton

Highlights: Historic cemeteries and wetland forests for birding

Rest Your Legs at a Beautiful Vacation Rental Nearby

If you need a place to stay for your Eastern Shore adventures, we have you covered! Eastern Shore Vacation Rentals has over 60 gorgeous properties in St. Michaels, Cambridge, Oxford, Tilghman Island, and beyond. Many of them feature pools, waterfront views, and easy access to your favorite activities while offering a peaceful escape from it all. We even offer pet-friendly options so that you never have to leave your loyal pal behind. Let us help you enjoy the scenery and serenity of Maryland’s Eastern Shore. Browse our selection of vacation rentals today and find your happy place!