Chestertown, Maryland

Betsy on the hard


Tucking tail for Chestertown was the right thing on several counts. Best part is it turned one adventure into two. It’s a cool little town, and I would have missed it if I hadn’t got run off the river.






A local bakery in the heart of the historic district offered second breakfast and a loaf of fresh bread for the boat, plus use of their wifi. It made a good home base for the next 24 hours. A lot of weddings in town for the weekend made it challenging to find a spare room, and nothing was cheap. Finally found something on the edge of town. Got a hot shower and came back.


Big Cat ~ Little Cat


There was space in the marina to park the trailer, next to a big catboat. A fellow walked up to ask about the Melonseed. Said he was having a classic rowing skiff built up in Still Pond. The second person to say I should stop in there. Took a walk through the town and headed back to the bakery.

Chestertown is an old and historic town. It was a booming port in the mid 1700’s, and the wealth brought by ship produced both lasting architecture and culture. Many grand old homes line the waterfront, a variety of shops seem to do steady business on the main street, and the college where George Washington got a law degree insures a constant population of youth and exuberance.



 Chestertown street view












It makes an intresting contrast with Rock Hall, just down the river. Chestertown is the county seat with the courthouse, and was a nexus of politics in the early years. Rock Hall is mostly a watermen’s town, more blue collar and hard drinking, with a lot of boat builders and craftsmen. The law-makers here, the law-breakers there. There’s a row of one room attorney’s offices next to the courthouse, each one seemingly trying to outdo the others in style. All want proximity to the courthouse, so they’re lined up like sideshow tents at the circus, and seem to be doing quite well. Advantage law-makers.


Attorney’s offices next to the courthouse


The people in town are really friendly. Several locals pegged me for a visitor and eagerly shared that it was First Friday, and that all the galleries would be open late serving free wine and hors d’ouvres. Sweet. Since I was blowing my budget on a hotel room, some free snackage for supper would be just the ticket. I could become an art critic for the evening, no problem.

There was some very good art, too. A watercolor show with dynamic, realistic paintings of watermen at work was especially nice. Maybe it’s just a coincidence, but it seemed the quality of the wine corresponded closely with the quality of the art, and vice versa. There was good and bad.











Bridesmaid, one of many


Rain came and went, but never much of it. In a sprinkle I ducked into a doorway next to the bakery and checked the latest on the weather. Someone nearby said, “You want to go for a ride?” I looked up and realized the question was addressed to me, by a pretty young barefoot woman straddling a rickshaw. Indeed.



Turns out there was a sort of Indian film festival going on at the theater across the street, complete with a talk by the film makers. Free curry and aromatic finger foods, and rickshaw rides in a pair of rigs they’d brought with them from India. I guess no one was biting, and I looked rustic enough to brave the drizzle and prime the crowd. Would not have guessed my first visit to Chestertown and my first rickshaw ride would occur at the same time. A nice way to tour the town, I must say. Video of the trip below.












Later that night, back at the hotel, the storms finally arrived with appropriate gravitas. Tornados did wreak some havoc in Tidewater Virginia and Pennsylvania. Here just a brief but intense storm. I went outside to have a look, and noticed Doug’s boat trailered up behind mine. Moments later we ran into each other in the lobby, and made plans for the next day.


A kids’ fishing tournament was scheduled for the morning at Turner’s Creek, closing the ramp until 1pm. I emailed a photo of the sign to Kevin. The new plan was to meet at Betterton and hope for reasonable facilities. We would meet there at 9am.

The next morning, on the way to Betterton, I stopped in Still Pond. The boat shop was closed up, but there was a sleek small log canoe in for repairs, and I managed a couple of shots through the windows.















3 Replies to “Chestertown, Maryland”

    1. Price was high, for sure, but the loaf was dense. Pound for pound it wasn’t a such a bad deal. Not great, but not bad. Let’s just say I shared and still didn’t finish it. Was good.

      More to come . . .

  1. Chestertown and Still Pond hold many fond memories from my youth. It is my favorite area on the Eastern Shore of MD. Love that shot of the Schooner Martha White.

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