Seeing the Eastern Shore by bike

Eastern shore Oxford MD loop biking 3

Biking along the Eastern Shore

To get to the Eastern Shore of Maryland, head east over the Chesapeake Bay Bridge, and you are there.  The Eastern Shore is actually a peninsula that extends for hundreds of miles between the Atlantic Ocean and the Chesapeake Bay.  You will find many fun things to do including beaches, historic towns, water activities and natural areas to explore.  It also happens to be a great place to bike, if you like to bike.

National Public Radio (NPR) recently ran a story about the Oxford-Bellevue Ferry, which operates on the Eastern Shore in Oxford, MD.  After hearing the story on the radio, my sister called me and basically said, “We should go biking on the Eastern shore and include the Oxford Ferry on our trip.”

That’s all the prompting I needed.  I’d wanted to bike the Eastern Shore for a few years, but wasn’t really sure how to go about it.  So I started searching for bike trails that included the Oxford Ferry.  I came across a bike trail known as the Oxford Loop, and as soon as I saw it, I knew it was the one for us.  Here’s a map, which includes that trip as well as others on the Eastern Shore.

We biked along the Oxford/St. Michaels Trail.  It’s about a 30-mile loop (our odometer actually said 34 miles), which we began in St. Michaels, MD, passing through the towns of Easton and Oxford, and then back around to St. Michaels.

Since we wanted to do the whole trip in one day, our day started early.  We are about two hours away and left in time to arrive in St. Michaels around 9:15 am.  St. Michaels is a small, but really cute touristy town.  We parked in the middle of town at the Chesapeake Maritime Museum.  After unloading our bikes, making final bathroom trips, and packing up our bags, we finally headed off at about 10:00.

The trail first wanders through St. Michaels a bit, taking you through the center of town and then along the water.

Eastern shore Oxford loop St. Michaels

Our first stop, still in St. Michaels

There were some beautiful homes in that stretch of the trail.  Then we headed down the main road to Easton, MD.  The road we were on had a bit of traffic, and the speed limit for the traffic was 50 miles per hour, so the cars were whizzing by.  I felt like we had plenty of room on the shoulder, but also felt like I was glad all of our kids were old enough to be very confident on a bike.

Eastern shore Oxford MD loop biking

Watch out cars, here we come!

At one point, we had to turn left on the main road at a traffic light.  So we joined in with the car traffic, used our hand signals and turned left with no problem.  The cars there are very considerate of bikers, but I was glad that we were comfortable riding with traffic.

In Easton, we found a fun, little grassy park where we stopped for a snack.  It was shaded and had benches, although most people were more interesting in standing or sitting on the grass since we had already been biking for about 12 miles.

Eastern shore Oxford MD loop biking park in Easton, MD

A shady park in the middle of Easton

After a nice break, we hopped back on our bikes.  The next stretch of our trip, like all the other parts, was on flat land, so the biking was easy.

Eastern shore Oxford MD loop

A stop on a bridge along the trail

Eastern shore Oxford MD loop biking 4

A view of the water along the trail

We were in Oxford, MD before we knew it.

Oxford was the highlight of our trip!  Natalie is still telling friends how she wants to live in Oxford, MD some day.  It is such a charming, quiet, friendly town.  As we biked down the main street of the town, we stopped and chatted for a while with a very nice couple.  They gave us tips on where to stop for lunch (the park right off the main road on the beach), where to get great ice cream (Scottish Highland Creamery on Tilghman Street), houses to check out near the ferry (a beautiful road near the shore), and some of the town highlights (currently a picket fence display throughout town).  It’s people like them that really added to the charm of the town.

We spent a couple of hours in Oxford—about one hour at the park having lunch and playing, ½ hour getting ice cream,

waiting for ice cream in Oxford, MD at the Scottish Highland Creamery

Waiting for ice cream in Oxford, MD at the Scottish Highland Creamery

and another ½ hour looking at the houses near the ferry and playing on the dock.

Eastern Shore-the dock in Oxford, MD waiting for the ferry

Natalie waiting for the ferry in Oxford.

We finally boarded the ferry to finish our trip.

Eastern Shore boarding the Oxford, MD ferry on bikes

Boarding the ferry with our bikes

The ferry ride took us across a part of the Chesapeake Bay, and took about 15 minutes.  The owners were so kind to us, and let all the kids take a turn “driving” the ferry.  Our ferry experience just added to our love of the Oxford area.

Luckily after the ferry, most of our trip was done—only because we had tired kids at that point.

Eastern shore Oxford MD loop biking 2

Making progress on our bikes along the trail

We had about seven miles left to get back to St. Michaels, which didn’t take too long.  We pulled into the Maritime Museum at around 4:00.

As we were finishing our trip through the main street of St. Michaels, my sister and I wished we were spending the night there because the area looked so fun for walking through, looking at shops, and eating.  And we wanted to visit the Maritime Museum too.

It you’re not up for a day of biking, still visit the Eastern Shore!  Visit the three towns that we biked through:  St. Michaels, Easton, and Oxford, then cross the ferry in your car.  Whether traveling by bike or by car, you are guaranteed to have a great day!…and to top it off you’ll probably meet some very nice people along the way.

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