Easton to Oxford to St. Michaels

Maryland’s Eastern Shore offers many things to do and one of them is great bicycle riding! My wife and I have always loved St. Michaels but have never taken advantage of the great bike riding that the area offers. Amanda has ridden her fitness bike from the St. Michaels yacht club and out towards Tilghman Island but we have never ridden the area together. Over Labor Day weekend we headed over to the shore to ride the Oxford St. Michaels loop via Easton, which would make for approximately a 30 mile ride.

For this ride we decided to park at one of the shopping centers along Easton Parkway (Route 33). Looking back on it when we do this ride again I would probably park at the St. Michaels Elementary School or make a weekend of it staying in St. Michaels to enjoy another ride the area offers and take in all the activities St. Michaels offers.

From the shopping center we headed out the Easton Parkway towards Oxford and made a right onto Oxford Road. The traffic was a little heavy between the shopping center and Oxford Road but the shoulder was generous so it wasn’t a big deal. Once on Oxford Road we began to enjoy the peace and tranquility the Eastern Shore offers. The road is flat and the shoulder generous as you head to Oxford.  As long as there are no headwinds, they can be noticeable on the shore; you should enjoy a pleasant journey through some farms, larger estates and a bridge crossing all offering great scenery. The scenery only gets better as you get closer to Oxford, with a population of less than 1000 the historical homes and tree lined street welcome you to town.  At the end of Oxford Road you’ll find the Oxford Bellevue Ferry which will take you over to Bellevue to allow you to continue your journey into St. Michaels. (Check out the pictures in the photo gallery.) Before you board the ferry to Bellevue take time to explore Oxford and take in the history dating back to the 1600’s.

The ferry cost $4 for a bike and rider for the short ride across the Tred Avon River to Bellevue on a busy weekend you will likely be joined by other cyclist for the ferry ride. This was certainly the case when we arrived and ran into a group of about ten other riders. Here Amanda’s new Project One Madone was the center of attention. It has an amazing pink flame paint job that is a piece of artwork; there are some photos in the gallery. At one point one of the riders said “You didn’t think you will be holding a press conference did you?”

 Once in Bellevue you’ll head out to St. Michaels via Bellevue Road. Your ride will be on nice quite country roads, once the ferry traffic gets by you, you’ll be left only to enjoy the piece and quite the Eastern Shore offers. Next you will enter Royal Oak where you will make a left to St. Michaels, just follow the signs. There are a few antique stores and a Bed and Breakfast in this small town, to enjoy. Once you leave Royal Oak you are heading out to St. Michaels Road (Route 33) which you will make a left to head into town. St. Michaels has something for everyone, shopping, restaurants, B&B, spas, the Chesapeake Maritime Museum and more. There is plenty to do in St. Michaels too much to write about here.

One of our favorite places is the Five Gables Inn and Spa located right on St. Michaels Road. Once you have enjoyed all that St. Michaels has to offer you just need to head back out St. Michaels Road, the way you came for your ride back to Easton. If you would like to ride more than 30 miles head out of St. Michaels the opposite way you came and you can explore much more of the area with such towns has Tilghman Island or Bozman. I plan to write more about this area in the future.

For those of you who prefer to stick with the 30 mile loop you will continue to enjoy wide shoulders and flat roads like you have your entire ride. Your journey back to Easton, will include farmlands and a great view of the Miles river at Newcomb. Once you reach Easton Parkway hang a left and head back to your car. If your time permits venture across Easton parkway to explore the town of Easton listed as “the 8th Best Small Town in America”.

This is a great ride suitable for road bikes, fitness bikes and hybrids. A mountain bike would be fine as well but I would recommend smooth tires. The roads are flat with generous shoulders; the only challenge might be if you encounter a headwind on a portion of your ride. This route would be suitable for the entire family; the only spot of concern would be immediately getting off the ferry in Bellevue. Just  wait a few moments for the ferry traffic to clear and you will be fine.

My recommendation would be to make a weekend of it since there is so much you can do. Stay in St. Michaels or one of the many B&B’s in the area. On one of the days take this route leaving from St. Michaels and head out to enjoy Oxford.  For a second ride head out of St. Michaels towards Tilghman Island and explore all the country roads (I’ll write more about this area in the future) or simply enjoy everything non cycling the area has to offer. Have a great ride! Be sure to check out some ride photos in the Gallery.

About Ernest

Ernest is the owner of the Crofton Bike Doctor located in the Village of Waugh Chapel Shopping Center. Ernest has been in the industry since 1989 when he first started to work at the Bike Doctor of Arnold. During that time I developed a love for cycling and retail. I graduated from the University of Maryland and live and ride locally.

I enjoy riding off road and on the road as well as doing a little bike touring. As a teenager I did a trip in Maine and then over to Novia Scotia which helped cement my love for riding. Since then I have done tours in the Canyons of Utah as well as several trips along the C&O Canal. Today I have both mountain bikes and road bikes that I enjoy riding. One of the most exciting things now is my wife is beginning to develop a passion for riding and we have begun mountain bike together as well as some light road riding.

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