Area Cycling Routes
There are many different types of riding in the immediate area of St Michaels but bicycle riders in the area will find one thing in almost all of them, magnificently wide shoulders. Maryland Route 33, or St Michaels Road, is one of Maryland’s most traveled secondary roads, but with the 8 foot wide shoulders, you will hardly know the traffic is there. Perfect for road, recumbent, tandem or tag-a-longs, you’re sure to find a distance that you will enjoy.

Tilghman Island (30 mile round trip)
Start from almost any point in St Michaels and head south on Route 33 for a beautiful, yet sometimes windy, ride to Tilghman Island. Most riders will stop at the Tilghman Island Bridge but if you do, you’re missing out on a quaint waterman village with a few small markets that may just surprise you. Continue down to the very end of the island, to Black Walnut Point, and check out a breathtaking view of the Chesapeake Bay. There is plenty to see on the island but just be sure to stop in one of the markets on your way out and grab a drink or a snack. There are no other markets on the way back to St Michaels.

Lowes Wharf Marina Inn (20 mile round trip)

Not up for the full 30 miles to Tilghman? Want to break up your ride in to a shorter jaunt? Try the 20 mile ride to Lowes Wharf Marina Inn, a hidden gem that only locals know about…. Until now! South on Route 33 again but slow down when you see the road sign for SHERWOOD. Look to your right to find Lowes Wharf Rd. If you’re a speed demon on that bike, you may just miss it! Enjoy their private beach, full bar and wonderful food. This ride is 10 miles down and a perfect trip before lunch. Then take your time and enjoy the spectacular views on your way back to St Michaels for a night on the town!!

Oxford Ferry Ride (15 or 30 mile trip)

Why two distances? Most people want to go and visit historic Oxford, Maryland either for the small town atmosphere, the local seafood, or Victor’s Ice Cream at the Scottish Highland Creamery. To ride straight there from St Michaels, travel north on Route 33 (towards Easton) and about 2 miles outside of town, follow the signs to the right to travel on Royal Oak Road. BE CAREFUL AS THERE IS NO SHOULDER. After about 1.5 miles, you will again follow the signs by turning right on Bellevue Road. Even though there are no shoulders here either, traffic is significantly less. Still be cautious as many travelers are taking boats on trailers down to the Bellevue Landing. Once you reach the landing, make sure that you have some cash on you. Current rates are $4 per biker, one way and $6 per biker for a round-trip ticket. The ferry travels every 15 minutes from each side so you may have to wait a moment but it is worth it. As soon as you get off the ferry you will be greeted by the Robert Morris Inn and you are only about 2 blocks away from that delicious home-made ice cream from Scottish Highland Creamery at the end of Tilghman Street.

If you’re out for more than just ice cream and a casual ride, why not go longer? For a nice 22 mile ride (followed by the short 7 miler back from the ferry), head northbound on Route 33 but DO NOT TURN RIGHT. Instead go straight, all the way up to the Easton traffic light. Make a right on MD Route 322 and after about 2 miles, turn right on to MD Route 333 (Oxford Road). Just keep pedaling and you will find yourself in Oxford. Stop in any number of the towns wonderful restaurants and enjoy lunch (and of course ice cream after) and then take the ferry back over towards St Michaels. DON’T FORGET SOME CASH FOR THE FERRY TICKET!!