The Eastern Shore

Written October 4, 2021

Jim and I have visited a bit of the Eastern Shore by car and done some boat training and boat shopping there, but this is our first time to really get to explore a bit of it. Something we were really looking forward to.

After leaving Havre de Grace, we headed across the Chesapeake and up the Chester River. We had a late start leaving Havre de Grace so decided to anchor part way up the river as it is 10 miles up the Chester River to Chestertown, our destination. We chose the Corsica River, a large tributary. We thought we’d have the anchorage to ourselves, but three other boats arrived and rafter up. There are lots of boaters on the Cheaspeake.

Our anchorage on the Corsica River looking up Emory Creek. We wanted to spend some time in the dinghy but we still seem to have trouble just saying we’ll spend another day. More schedule than we’d like sometimes.


The next day we headed up on to Chestertown where we had a mooring at the City dock for 1 night. We’d wanted to come here as we’d heard it was a pretty and very “original” Colonial town and also, Jim has ancestors from this area. I know, we are doing the genealogy thing again! Jim has 3 sets of 6th Great Grandparents who arrived in Kent County, MD, a couple 7th Great Grandparents and and a handful of 5th and 4th’s. Gale, Rasin, Everett, Moore and Medford; the family names. Lots still not completely understood of these families, but they arrived in this area as early as 1662 (or there abouts) and had migrated on to Kentucky ad then Indiana by the late 1700’s. These are the roots of Jim’s maternal Grandmother Ollie Long’s line that ended up in Illinois. As a child Ollie came with her family to Arkansas where she married and had Jim’s mother Liz. But back to Kent County. One of the concrete piece of evidence of this clan was the marriage of Rasin Gale and Martha Moore in St Paul’s Church in Kent County, MD in 1755. Amazingly, we’d driven past the church when we were boat shopping 4 or 5 years earlier. We finally got to visit it.

The church was established in 1692, a wood frame building. This building was built in 1713 is the oldest continuously used Episcopal Church building in Maryland. Just think, Jim’s 5th Great Grandparents were married inside this church. Amazingly, in this age were churches are no longer open for people to freely visit, this church was. What a treasure to be able to see the inside.
I imagine the inside of the church is much nicer than it was in 1775, but a pretty little church.

Pic inside

We looked around the cemetery here and visited several others as well as taking in the ambiance of the area. Unfortunately, I’ve yet to be able (and may never) discover where anyone is really buried. These families were plantation owners and sadly were slave owners, but this area of Maryland does not seem to have any of the old plantation houses still standing. I’ve gathered some information fro the historical society and have the card for their genealogist so we’ll see if I can uncover any further information.

Chestertown is a very cute town though. Full of it’s own ambiance and old world feel. Apparently it is one of the towns with the most Colonial brick building still around.

There were MANY buildings such as this around town. There is something very warm and inviting to them.

Plus, lots of very pretty streets that are a joy to wander.

Street after street of cute houses. They really get into fall decorating as well.

We’d managed to extend our stay a day (turns out it was my Birthday and we really wanted to spend another day anyway). Saturday was farmers market day. As well as lots of produce, there were meats and seafood and crafts and dairy. A very nice market!

One of the many vendors at the farmers market

To top it off, there was also the Chestertown Car Show that afternoon! Who could have asked for more? It was fun to see a different batch of cars than the ones we see at every car show in New Mexico (although there were lot that could have been transplanted with ease.) A good show though. Not too big, but some fun stuff to see.

Ok, you might see a Morgan at a New Mexico car show. I though this car was particularly pretty.
I have a soft spot for Thunderbirds

The other fun part is the replica sailing ship that was moored across the dock from us. Twice daily it takes folks out for rides. I have to say, we’ve been docked next to some pretty interesting boats on this trip.

Our dock mate. We had a very quite spot on the dock which we loved.

Chestertown is a hidden gem that many folks apparently do not visit. Our luck!

The Kent Narrows

It was a half day trip back down the Chester River and through the Kent narrows to St Michaels. The Kent narrows is the short cut to St Michaels through a narrow passage. This area has now been developed with marinas and restaurants and the landing point for the Chesapeake Bay Bridge on the Eastern Shore. This bridge is not an issue, but there is a very narrow and shallow dredged channel from the north from the Chester River to the narrows. It is well marked, but on a Sunday afternoon, it has lots of traffic. The mean low water in may places is 6.5 feet and we have a 5 foot draft. The channel is not terribly wide and can quickly silt up. The Tow Boat US guy was waiting in one of the harry turns for a “patron”.

See the red nun (mark) on the right and the one in the distance, and the green post on the left? One had to stay within these lines as the water quickly dropped to 2 – 3 feet outside of this channel. Yes, the traffic as this crazy, it is not an illusion. Just beyond the larger blue hulled boat was the Tow Boat US boat, waiting for business.

Once you get through the channel, it opens up by the marinas and restaurants. But there is a bridge with 18 foot clearence. Time it for the hour or half hour requested opening. Only 3 boats needed the openinng as many/most did not plan to go through or were short enough they could slip under. A good current through this narrow bridge opening. On the other side, open water and little traffic. A crazy spot but saved several hours and fun, especially as we did not ground ourselves.

St Michaels

After Chestertown, I was a bit nervous to visit St. Michaels. Everyone says you must go, but all the hype made me worried I might find it a tourist trap. The anchorage was quite crowded, but we found a nice spot and slipped in and dropped the hook. Turns out we learned the next day there was a small boat show over the weekend and this undoubtedly added to the traffic. The anchorage has about a third of the boats as last night.

We visited the maritime museum today. Lots of interesting exhibits. Each maritime museum, of which there are many on the east coast seems to be unique enough to be enjoyable. One of the things they are doing here is building a reproduction of a big sailing ship. We chatted with one of the guys making rigging for the boat which will go to St Marys when complete.

There are something like 13 full-time boat builders working to build the Dove, the boat that will sail to St. Marys next year. This guy is working on rigging for the boat while others are completing the wooden hull. Int eh background in one of the masts. This ship will be similar to the one we were moored by in Chestertown.

The museum has lots of old boats, some in the water, some on land. My head is still swimming in all the types of boats and how to tell them apart and their special purposes.

A few of the floating stock at the museum. Please do not ask me to tell you about these different boats and what they were used for. They all had a life on the Chesapeake and most (all?) were real working boats in the bay.

There are lots of quaint buildings here as well, but I particularly likes this lovely bridge just after the dinghy dock heading into town. There were people there updating the flowers on the bridge as we walked across.

Across the bridge is town. To the left is part of the harbor. What a nice entrance for visitors arriving by dinghy.

We’ll spend a bit more time in St. Michaels tomorrow at the museum then probably head up the Wye River for a night. Still planning our next few days.

St Michaels in the distance from our anchorage. A lovely evening after an enjoyable day in St. Michaels.


The Eastern Shore — 4 Comments

  1. Once again you’ve taken me into your adventures. So interesting to see and hear about places I will never see in person. Thank you

  2. Loved the bridge at the dinghy dock. Much nicer than the dinghy dock we experienced at Contrecoeur, which was admittedly under renovation. The weather much nicer too. In fact you seem to be having a spate of great fall weather. Yippee. Hope it holds

  3. Apparently fall is the best time on the Chesapeake and it does seem to be the case. We have had a bit of wind the past couple days and some sprits of rain, but still pretty darn nice.