Saint Michaels: the Heart and Soul of the Chesapeake Bay

May 15, 2023

We’ve been zig zagging across the Chesapeake going from one town to another. There is so much to see and do, but not enough time.

Saint Michaels was next on our Must Visit list. When reviewing the Great Loop Facebook page, there was discussion on a few loopers’ anchors dragging; however, those people were on the north side of town and we were going to anchor in the southern side.

We thought to be safe, we would put out a little extra chain (or all of it). 175 feet of chain in 10 feet of water later, we were rafted up and secure. A few other looper boats joined us in the bay as well including Bama Breeze, Beach Side, Pu Hana, and eventually Fika.

The anchorage was great. The only possible issue was the number of crabbing boats cruising by. I’ve never seen this manner of crabbing. They’d drop a weighted line with little sandbag-like-bags that the crabs would grab onto. The fishermen would come by and pick up the line, catching the crabs at the surface with a net or basket. We weren’t bothered by them and it was fun to watch this method of crabbing.

Up the bay was a small dinghy dock that was a few blocks from the heart of town. The town itself is a grid pattern around a central square. The streets are lined with cute houses and shops as well as a museum and waterfront. This is one of my favorite towns so far.

What makes this town interesting, besides sharing a name with my son Michael, is its role in the War of 1812. The British was planning on attacking St. Michaels, but the town knew of this plan and hung lanterns in trees beyond the town. When the British attacked at night, they saw the lights and overshot the town. Only one cannonball hit a house and the town became known as “the town that fooled the British.”

Our first day arriving in St. Michaels, we headed to town to see a distillery and do some wine tasting. I also tried some Chesapeake Gold cheese which was delicious. The first winery, St. Michael’s Winery, had an amazing selection and I went home with some Gollywobbler Peach. I loved the taste and the name. Apparently, a Gollywobbler is a staysail set between the foremast and mainmast of a schooner.

The second winery, Bordeleau, wasn’t bad, but their tasting fee was a little on the higher side ($18 for 5 pours). Thankfully, the pours were generous, but I didn’t bring any home.

The Windon distillery made delicious Lyon Rum. We enjoyed sampling many flavors and types, but my favorite was the coconut rum.

The rest of our stay included walking, shopping, exploring, eating, and even a day of swimming in the bay. After many locals recommending Avas, we went for dinner with a bunch of other loopers. It was great getting to know more people and sharing travel tips.

Here are some photos of our exploration:

When leaving in the morning, we watched the crabbing boats slowly boat around. I was a little concerned with where their lines may rest and discovered one was caught on our anchor when we started pulling her up. A little nudge with a boat hook released it and we were on our way to our next destination. Sadly there were no crabs attached to the line.

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