The Oxford/St. Michaels Route is Recognized as One of the Top 25 Cycling Routes in the United States
Distance 29.6 miles
Pedal your way through history, charm, and Chesapeake Bay beauty on this beloved biking route through Talbot County.
The Oxford-St. Michaels Loop is recognized as one of the top cycling experiences in the region, offering quiet roads, waterfront views, historic towns, and unforgettable local flavor.
Your Journey Begins in Oxford
A postcard perfect waterfront town known for its boat-building heritage, charming restaurants, a delightful general store, and the Oxford Museum. Don’t miss a scoop at the award-winning Scottish Highland Creamery, where handmade ice cream is served with a view.
Crossing the Tred Avon River aboard the Oxford-Bellevue Ferry, one of the oldest privately operated ferry routes in the nation, is one of the loop’s biggest highlights. In continuous service since 1683, the short ride provides a peaceful pause with great photo opportunities. Visit oxfordferry.com for current ferry hours and to purchase passage.
Note: the ferry does not operate in colder months.
Ride through Royal Oak, a small crossroads village with open farm fields and a post office that feels frozen in time. Continue to St. Michaels, one of the Eastern Shore’s top destinations. You’ll find boutiques, galleries, fresh seafood, and another two more sweet stops on the main thoroughfare—Justine’s Ice Cream Parlour and JoJo’s Ice Cream.Safety Tip: Ride single file and stay alert on Royal Oak Road between Bellevue and MD 33. The road here is narrow and bordered by deep ditches. In the summer months, it’s not uncommon to meet large equipment as farmers move from field to field to till their crops. The views are worth it, but you’ll need to use extra caution.
