Chesapeake City. Will the “firsts” ever end?

The current and tide dictated an afternoon departure from Delaware City on Sunday so we decided to make it a short day and stop on the other end of the canal in Chesapeake City.  Applying our lessons learned from running into the dike, we carefully reviewed the chart for our intended route and also looked at Active Captain and the Coast Guard’s Local Notice to Mariners.  Anything we weren’t sure of we looked up on Chart Number One, and we wrote reminders on a write on/wipe off board that we had purchased at Staples in Delaware City.  Although I was nervous leaving, all of the preparation made for an overall much less stressful trip.  It looks like we have a new evening routine from this point forward!

While the C&D is reportedly the third busiest canal in the world, we didn’t see any freighters as we motored along.  Not that we were disappointed about that given that they take up their half and the middle too. 

Looks like a freshly painted bridge on the canal – nice shade of blue!

It was an uneventful afternoon and soon we found ourselves setting the anchor in Chesapeake City.  It was a pretty tiny anchorage with stone walls a bit too close for comfort on three sides of it, but we were quickly snuggled in.  I wanted to check out the C&D Canal Museum the next day, so we had decided to stay for two nights and leave on Tuesday.


Although the anchorage filled up that evening, it was a quiet night and we spent Monday morning checking out the museum and poking around Chesapeake City.  While it was cute, there wasn’t much there so we were definitely ready to leave the next day.  Had we known what would happen late that night, we would have left earlier.

Bundled up against the chill and the rain showers.

Cute houses in Chesapeake City.

Around 5:00 p.m. we heard “Ahoy, Pegu Club!”  It was Judy and Steve on s/v Bentana.  A mutual friend from Shenny had connected us and we ended up having a nice visit that evening on their boat.  We picked their brains on the subject of cruisers etiquette, and we are looking forward to seeing them again in Annapolis.  Turning in slightly before cruiser’s midnight, we hit the sack planning an early departure from Chesapeake City.

In the middle of the night we woke up when we felt the wind shift 180 degrees and pipe up to 20 knots.  That’s when we found out that the anchorage at Chesapeake City has poor holding.  Moments after waking up our anchor alarm went off.  We were dragging.  For the first time.  In a crowded anchorage.  At 2:30 in the morning.  

We weren’t the only boat dragging.  We heard someone’s horn toot to alert others, and the blue trawler near us had already raised its anchor and was reanchoring near us.  Another sailboat was also in the process of reanchoring.  Much too close to the stone walls and the other boats at this point, we threw on our jackets, fired up the engine, and raised the anchor.  But where to go?  Did I mention the anchorage was crowded?

Over the next hour we made several attempts to put the anchor down, each time finding ourselves way too close to other boats by the time we let out a decent amount of scope.  The blue trawler had basically taken our spot, the wind was still gusting to 20 knots, and I could barely see anything in the dark.  Jeff came back to the cockpit and said, “We need an idea.”  “I know we do!”.  We looked at each other, and then he suggested going up to the city dock which looked like it had enough space between two other boats.  I said there was no way in hell I was going to parallel park Pegu Club at a dock in the middle of the night in 20 knots of wind.  He kept trying to convince me until I looked at him and firmly uttered our motto, “Most conservative wins. I’m not doing it.”  

Eventually we found a place to anchor closer to the mouth of the anchorage and agreed we would take turns on anchor watch. I volunteered to go first while Jeff slept in the main cabin.  After 45 minutes the wind had eased and we clearly hadn’t moved based on our anchor alarm app, so I went down below and told Jeff that I thought we were o.k.  We crashed for what was left of the night, and as we left Chesapeake City we decided that one visit was enough.  Some googling after the fact turned up many anecdotes of the anchorage’s poor holding when the wind kicked up, with many people saying they would never anchor there again.  Add us to that chorus! 

8 thoughts on “Chesapeake City. Will the “firsts” ever end?

  1. Hopefully only the bad “firsts” will come to an end and be replaced by all the great ones to come!! Just think of what it’ll be like when you’re sitting in a calm Bahamas anchorage watching the sun slip into the ocean (cue green flash here) while enjoying your beverage of choice!! That will make it all worth it!! Be safe!! Jeff and Denise…

    Liked by 1 person

  2. We also spent a couple of days here. Nice quaint town, a couple of other sailboats in the anchorage. No issues with holding, but then again the winds never exceeded 10kn, might have touched 15kn briefly.

    Liked by 1 person

    1. I think it might have been o.k. if there hadn’t been an immediate 180 right before the wind piped up. Hard to say. I’m not anxious to test it out again in that anchorage any time soon! Kimberly


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