Exploring the Eastern Shore of the Chesapeake

Before we had left Vero Beach, a friend had recommended reading James Michener’s Chesapeake while we cruised the area this summer. It was a wonderful suggestion, and we have both read the saga. As Michener is an amazing writer, capable of bringing to life areas in all of his stories, we were excited to see firsthand the landscape and areas from his book. As most of it takes place on a fictional island on the Chesapeake Bay eastern shore, we couldn’t help but look for comparisons between reality and storytelling. We agree with Michener’s recounting – the wilderness of the eastern shore inspires musings of what it must have been like 100, 200, 400 years ago and more.

Sept 14:
We left the Worton Creek anchorage and cruised down the Chesapeake to the Chester River. The estates along this river (and most of the rivers along the Chesapeake) are breathtaking. We had an additional trivia moment when we anchored in the Corsica River in a small bay in front of an old Russian government vacation dacha located on 45 acres – one of the compounds that was “reclaimed” by the US as part of the 2016 dispute over Russian interference in the US election, and we were told that, sadly, it sits empty gathering dust. There obviously is a lot of history – both centuries old and more recent – in this area.

Entering the Chester River, MD
Choppy seas

The cruise was surprisingly comfortable as there was a small craft advisory for the Bay, with 15-20 knot winds. Kathleen noticed that it makes a HUGE difference in comfort if you are cruising WITH the wind as opposed to INTO the wind (as well as giving us a bit of a speed boost). As we rode with both current and wind, with only 1-2 foot swells, the ride was smooth, and we even saw a whopping 10 knots at times!

Unfortunately, along with a return to brackish water, we were back into jellyfish territory, so no swimming at the Corsica River anchorage. Weighing anchor the next morning, we used the wing engine. It is an auxiliary engine (27HP, 3 cylinder Yanmar diesel) coupled to its own shaft with a folding prop, and is used in case there is a main engine and/or drivetrain failure. It is mounted off the centerline, port side, and can propel the boat 3-4 knots. However there is a persistent starboard steer. It’s really important to run the Yanmar to to keep it in good operating condition. We have heard too many stories where the wing engine will not run when really needed (during an emergency or a boat purchase survey) due to lack of use. This is what Neil has told Kathleen many times, and she keeps repeating to herself under her breath while being frustrated trying to drive our girl at such a low speed and challenging steerage…

Circled in above photo – The auxiliary engine shaft and folding propeller located on port side of hull
Close up view of auxiliary propeller in folded position
Auxiliary engine throttle cable sticks and won’t hold the full throttle position. Clipboard acts as low tech cruise control until we fix the issue, most likely replace the throttle cable that snakes all the way from pilothouse down to the engine room. On the fix list when we visit Zimmerman Marine in North Carolina early in November.

We anchored 11 miles further up the river, just outside of Chestertown, a wonderful colonial town on the Chester River (maybe not the most creative town name, but it works). After anchoring, we lowered the dinghy, and drove up to the harbor. We docked, intending to get some gas for the dinghy, but as seemed to happen often for us, that particular day the marina and fuel dock were closed. Not to be deterred, we explored the area, enjoying the historical architecture and using an app for a self-guided walking tour for a bit of the neighborhood. We capped the afternoon off with a light meal at the marina grille before heading back to our anchorage and our home. All day, the sun was hazed over, but we couldn’t see clouds. It was the smoke from the west coast fires, up in the atmosphere. It didn’t affect us at all that we could tell, but it was eerie and incredibly sad that so much had burned that it had covered our skies so far away.

At anchorage near Chestertown
Hazy due to smoke from west coast wildfires
Schooner SULTANA at dock in Chestertown harbor. It is a replica of a 1768 British revenue cutter and used as a schoolship for educating students on the Chesapeake Bay
Seeing the historic sites of Chestertown
Chestertown’s historic downtown
A well deserved break for a refreshment
River Packet cruise ship passing us at our Chester River anchorage

One of the more mundane tasks that we easily do and for the most part, without a lot of forethought while on land, is grocery shopping. We no longer have a car, and in these pandemic days, it makes the logistics a bit more tricky, as Uber and Lyft are few and far between in marina areas. We set out with totes and a rolling cart (always a good look) and had a pretty walk to a grocer, through historic Chestertown, a large portion through a tree lined, shady walk, with leaves just beginning to flutter down around us, another reminder of the changing seasons. Once we loaded up as much as we could – backpacks, totes, rolling cart – we headed over to the nearby CVS pharmacy for a flu shot and then headed back to the marina to load up our dinghy, realizing how glad we were that it was as big as it is. Oh, and Neil filled up the dinghy gas container at the marina.

Hiking a couple miles to the nearest grocery store

After a great dinner, we partook of one of our favorite activities – stargazing. We watched the stars in the evenings here – less light pollution – and were greatly rewarded with Jupiter, Saturn, gorgeous moon, Mars, Big and Little Dippers, Polaris, and our new favorite, Cygnus (cuz it’s easy to find). We wouldn’t feel comfortable tossing the radar and navigating by the stars (props to those who do), but it beats Netflix every time.

The next day, September 17th, we cruised back out to the entrance to the river, across from our original anchorage so we could have an early start the next morning, with fewer miles to travel. It was a bit of a rest day, as we caught up on boat chores and chatting with family.

Leisurely cruise back down the Chester River

One thought on “Exploring the Eastern Shore of the Chesapeake

  1. Very envious of your lifestyle. Wish you nothing but the best in your travels. Can’t wait to see what you post next time. Take care.


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