Challenging Rides in Kent and Cecil County, Maryland

Last summer I found a website with three rides all starting in Chestertown, Maryland on the Eastern Shore. I did the shortest of the three last summer. This past month I went back to knock off the two 80–ish mile rides.

The first ride, called the Historic County Loop actually covers much of the ground of the shortest ride. Still I managed to make a wrong turn or two and stretch an 81-mile ride into 86 miles. It’s a talent.

To be honest the maps and cue sheets are old so it’s not surprising that I got lost. That’s my story and I’m sticking to it. I mean your talking about somebody who did the 50-States Ride in DC 11 times and still missed the first turn on his 12th ride.

The roads in Cecil and Kent Counties are in good shape. Higher speed roads have very wide paved shoulders. There’s a bit of truck traffic probably because these routes are close to US 301, a major divided highway running north and south. Most of the roads I was on are marked as bicycle routes so local drivers are used to seeing bikes on the road.

The Historic County Loop travels through miles of farmland and diverts now and then to the Chesapeake Bay. To be honest, I’ve seen better bay views in a dozen other places. The farms appear to my city-dweller eyes to be corn and soybeans. If you spun a Hoosier around they would swear they are right back home in Indiana. If memory serves, Indiana farms are much bigger, but these farms will do nicely for visual purposes.

I did the second ride, called the Pump House Primer, a couple of days ago. This one is a bit more interesting. Once again I encountered corn and soy but over the line in Cecil County the terrain became more rolling and the farms were a bit more diverse. One farm had a stand of hops (they grow on wooden poles). Another had some sheep. The most interesting farms were stud farms for breeding thoroughbred horses. These farms look very much like those in central Kentucky. Unfortunately, I couldn’t manage a decent picture of the horses. They are beautiful beasts.

One highlight of the route is the descent to a drawbridge over the Sassafras River. The bridge connects Georgetown in Kent County with Fredericktown in Cecil County. The drawbridge has a metal grate for a surface so rider beware, especially when it rains.

The northern most point of the ride is at Chesapeake City on the Chesapeake and Delaware Canal, which connects the Chesapeake Bay in the west to the Delaware River to the east. Years ago I rode on the Canal trail which is worth doing if you’re in the area and aren’t already mashing out 80 miles on the roads.

The ride back from Chesapeake City makes a small loop. The route then starts another small loop, or so the cue sheet and map say. Alas, one of the roads on this loop is closed. I checked it out and found a barrier across the road and woods beyond. From the age of the trees and underbrush, I suspect this route map is more than a decade old.

Using my phone, I improvised a course correction and managed to screw that up. I back tracked and found a road on the cue sheet. Following the route, I rode 19 miles back to Chestertown, going back over the first 19 miles of the ride. I ended up riding 78 miles with a nice tailwind for the last 14 miles. As it turns out, the part of the Pump House Primer route I lopped off was on the Historic County Loop route so I actually didn’t miss a thing.

I did these rides on The Mule but need to try them again on Big Nellie. Level and gently rolling terrain is what recumbent bikes are made for. All I need is a repeat of the amazing weather I had for these two rides.

If you are interested in these rides, plan to spend some time wandering around Chestertown, Chesapeake City, and Georgetown. They are small towns with buildings dating back to the 18th and 19th centuries.