Session 28-Rock Hall & Chestertown, MD-Hitting Bottom

Are you ready for the action sequence of our journey? Have you been waiting for it this whole time? Well, you’re in luck.

There is a very good reason many boaters encouraged us to purchase a Tow Boat US yearly membership. Long story short—shi# happens. 

If you’ll remember, Tom and crew had to use the same tow service on Therapy’s maiden journey to Marathon Key way back in 2019. The ram-rod apparatus busted and the boat needed towing a short distance into the marina. All ended well.

Fast forward to Tuesday, September 22 as we pulled into Rock Hall harbor in Maryland. As we slowed and started to cut across the center portion of the basin, there was a bit of a bump then some…stoppage. In the middle of the basin, we hit bottom. We were close enough to the marina for Mahomes to hit it with a football, but stuck all the same.

The marina lady told us through the VHF that it happens all the time. She sent out one of her guys with some sort of boat-pushing device to try and back us up the direction from whence we came to no avail.

Boat-pushing fella suggested we call Tow Boat US and that’s what we did.  45 minutes later he appeared—The Tow guy. He hooked us up and eventually freed us from our spot and guided us back into the deeper channel. 

We worried about damage to the props, but we seem to have come out of it unscathed. Plus, we provided lunchtime entertainment for the many, many diners and boaters coming in and out of the basin. 

We spent one night at Haven Harbor Marina in Rock Hall which turned out to be a very nice marina with a lovely sunset spot. After getting stuck in their harbor, however, one night was sufficient for us.

We took off very gingerly the next morning so as not to drag the bottom on our way out. No worries. The trip up the Chester River ended up being gorgeous and sprinkled with stately homes and a few that we would consider compounds.

 We slid easily into a very new Chestertown Marina set in a picturesque spot along the river with the historic part of town just a three block walk. We, however, opted to take the courtesy trikes—yes—I said trikes. They were in great shape and each was complete with a basket. I’m sure we were quite a sight.

Side note:  Have you looked at the state of Maryland—ever? It’s a funky shaped little state and I feel sorry for those elementary kiddos who have to draw it or make a diorama because it can-NOT be easy.

Anyhoo, Chestertown  was founded in 1706 and boasts the second largest collection of 18th and 19th century structures in Maryland second only to Annapolis. I particularly enjoyed the old churches and their chimes throughout the day. We don’t have that in our neck of the woods. 

We were able to take in the local farmer’s market while there even though it was a rainy day. Dinner that evening ended with a dessert of the red velvet kind. We got a chuckle reading the circled item on the menu. I’m betting the weekends can be an ok time to be kitchen help.

We really enjoyed every part of Chestertown. It is a lovely town in a lovely setting with a lot going on. There are several festivals throughout the year and I am sad to say that we missed the  Harry Potter Fest October 2-3. Maybe next year. 

We made the short trip from Chestertown up to Annapolis on Sunday, September 27th. This is where I realized that the back pain I had been experiencing in Chestertown was going to present a real challenge. Stay tuned.

Categories: Uncategorized


  1. Endless adventures💕


    • Oh dear Julie. What’s with the back pain? My sister lived in Chestertown and I went to middle school there. Peggy also lived in St Michaels. Annapolis was my home town for 15 years so your trip is to places very dear to me. Please let me know about your back


      • Jo, I am much better now. Still having a bit of trouble with it but sleeping and getting around much, much better. We are currently packing the boat to head home for the winter. I hope all is well in your world.


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