Halloween in St. Michael's

posted by Ardys

Our first night out from Annapolis on our voyage down the East Coast, was a short hop to a charming little town, St. Michael’s on the Eastern Shore of Maryland.  The plan was to meet up with old sailing friends from Duluth, MN who coincidentally, were in the Chesapeake and planned to sail to St. Michael’s with another couple of our mutual friends to spend Halloween.  A delightfully charming little town, and if it’s possible, even more so on Halloween weekend.

 We sailed to St. Michael’s earlier this summer, and, one evening while at anchor in the Miles River, our boat was surrounded by a large group of dolphins who swam around our boat.  They parted at our bow, swam the length of our boat and then slowly moved beyond our stern.   Splashing and moving so slowly, we had to assume they were feeding on the fish schools we’d seen earlier.  There was a full moon, and although not bright enough for photography, at least not with my equipment, we were able to visually follow at least 5 small groups of dolphins at the surface, enjoying their banquet, no doubt.  It was marvelous!  

While we were in Annapolis last summer to buy our boat, we drove over the Chesapeake Bay Bridge to explore the Eastern Shore.  We followed a road to the end of one of the Eastern Shore peninsulas and happened upon St. Michael’s quite serendipitously.  We didn’t know at that time that St. Michael’s is a very popular sailing destination for Annapolitans.  It’s an easy 5 hour sail, give or take, across the Bay.  Houses from the 1800’s, brick sidewalks, picket fences, narrow streets, art galleries, and of course, the tourist trap boutiques which are all very nice, albeit expensive. 

I would recommend the Chesapeake Bay Maritime Museum to anyone.  The history of the Chesapeake Bay and the watermen who have worked on it for decades is very well presented.  There are craftsmen demonstrating wooden ship building on site.  There is an array of historic boats such as the skipjack (a long, narrow sailboat with an incredibly long boom) used for oystering before the oyster population was fairly decimated, and one of the remaining log canoe sailboats which still competes in sailboat races on the Bay. There’s a screw-pile lighthouse that’s been transplanted onto museum land for guests to tour and so much more.  Allow plenty of time to see it all.  

 We tried out a few of the restaurants in St. Michael’s over the course of our three visits.  We really enjoyed Ava’s Pizzeria and Wine Bar, somewhat of a hole-in-the-wall kind of place from the front sidewalk, but with great food, delightful outdoor seating and dog friendly wait staff.  We also really liked a restaurant about 2 1/2 miles outside of St. Michaels’ called Chesapeake Landing Restaurant and Seafood Market where my husband and his nephew, Hayden, shared 2 dozen crabs.  I didn’t feel like putting that much effort into feeding myself that day, and ordered something that I didn’t have to smash with a mallet.  We got it on good authority from a volunteer at the Chesapeake Bay Maritime Museum that that was where the locals went to eat crab and no wonder, it’s less expensive than some of the harbor front restaurants.  There are no fewer than three dog friendly ice cream shops (high on my list of what makes a good walking tour on a hot summer day) and the Eastern Shore Brewery serves patrons during daytime hours— also dog friendly.  It even has its’ own resident dog, an enormous St. Bernard puppy named Barley.  

There couldn’t have been a more beautiful, warm autumn day for Halloween in St. Michael’s.  The little town filled up with boats, many displaying their own Halloween decor, such as a 6’ diameter blow-up pumpkin, orange lights, cobwebs covering the bow and giant spiders climbing the sides of the boats.  One remote controlled bat hovered nearby while we enjoyed a happy hour on our friends’ boat.  There was, of course, the odd pirate or two strolling about, along with other festooned characters.   The main street shops were dressed in all their spooky best, and the entire little town seemed to be up for a “spirited” holiday.  I suspect that St. Michael’s tends to gear up well for other holidays, too.  In fact, I wouldn’t mind spending some other holidays in St. Michael’s just to see.