St. Michaels, Maryland {Trip Report}

I hope everyone had a great holiday weekend and enjoyed the unofficial end of summer!

Nick and I spent our long Labor Day weekend in St. Michaels, a charming little waterfront community along Maryland’s eastern shore. We had perfectly sunny weather and temps in the high-80s all weekend.

The town of St. Michaels is small and quaint and filled with boutique shops, a winery and brewery, restaurants offering Chesapeake seafoods, and cute little cafes and inns. This was our first visit, which we’ve been looking forward to all summer, and it was definitely worth the wait.

We left our marina Friday morning with light winds, but we were able to put up the sails for a few hours of the trip. We anchored our boat in San Domingo Creek, commonly referred to as the “back door of St. Michaels”, which is much quieter than the busy Miles River marina and harbor on the other side of the city.
St Michaels
When we arrived Friday afternoon we were one of only a couple of boats in the anchorage, but by Saturday night there were nearly three dozen other boats surrounding us.
On Saturday morning we took our dinghy into town and headed to the Chesapeake Bay Maritime Museum. The museum consists of a lighthouse and a variety of old, preserved buildings that house marine artifacts and help tell the story of the Bay’s maritime history and seafood harvesting. We even toured an old boat building warehouse where they still teach the craft of wooden boat and oar making.

After touring a few of the buildings we made our way to the museum’s annual charity boat auction. There were probably 100 boats being auctioned, everything from old wooden kayaks to 1950s speed boats and modern sailboats.


We helped cheer on the winning bidders of the boats for a few hours before ending our evening at the Eastern Shore Brewing Company for a pint (and a growler to go) and then making our way back to the boat. Our favorite brew was their Knot So Pale Ale.Nickbrewery

We were just finishing dinner that evening when Nick noticed out of the corner of his eye that a sailboat was headed our way. The family had arrived early evening and quickly anchored and rowed into town. Unfortunately, no one was on board and it appeared their boat was dragging its anchor (every boater’s nightmare!). Had it gotten close enough to us, we could have rafted it to our boat, but the wind pushed it closer to shore. We watched with sick stomachs as it floated toward the rocky shoreline and hoped that it would eventually ground itself in the shallow water; luckily, the winds shifted and it eventually wedged itself along a private dock, with no damage to either, where it sat until the owners returned later that night.

anchorboatWe ended the evening with a nice fireworks show that we watched from the bow of the boat.

On Sunday morning, before it got too hot, we paddle boarded around the entire creek, which is surrounded by large beautiful homes. After a late breakfast we took our dinghy back into town for more shopping and exploring. There are so many cute nautical clothing and home goods stores along the main strip.

After a few hours of shopping and exploring the town, we stopped at St. Michaels Winery, where we bought a bottle of their summer white and sat outside to enjoy the nice weather and people watch.

NickwineryLater that afternoon, we headed to the Crab Claw, a St. Michael’s institution, for some Chesapeake Bay crabs on their waterfront patio. It was messy, even after the waitress gave us a demo on how to properly eat crabs, but we still had a great time!


Our on way back to the boat that evening, we came across a couple on a kayak that was taking on a bit more water than they were comfortable with and so we gave one of them a ride back to their boat in our dinghy; they ended up being from our same marina!

After three days at anchor (our first!), on Monday morning we weighed anchor and headed for home (that and our low battery alarm woke us up before dawn, and we figured if we needed to start the engines to charge the batteries we might as well just head home! 🙂 )

All in all, we really enjoyed our time spent in St. Michaels, and definitely plan to visit again. If you ever have a chance to visit this cute little town, I’d highly recommend it!


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