Destination reached: St. Michaels, MD — Road Trip 2020

Boats, St. Michaels, MD

Perhaps your GPS talks like ours does: “You have arrived at your destination. Your route guidance is finished.” And when “she” told us we had arrived (for only the second time in our lives) at our chosen spot — St. Michaels, Maryland — we were glad we had braved the pandemic to spend a few days with harbors, quaint homes, and great seafood on the Eastern Shore. It’s no wonder St. Michaels was named one of the Top 10 Small Coastal Towns in America by USA Today!

Waterfront, St. Michaels MD


We weren’t really sure we could find a place to stay when we were planning this trip. September in St. Michaels is prime time for tourists, so many of the quaint BnB’s were booked, at least for the weekend. But the Old Brick Inn, with five properties in town, had a vacant cottage on a quiet street waiting for us — and free gourmet breakfast the next morning served in an outside courtyard!

St. Michaels Lifestyle

People who live in St. Michaels or come for extended stays have no problem finding things to do. After all, it’s the Eastern Shore. So, fishing, boating, and relaxing probably rank high on anyone’s list.

Tools of the trade:  St. Michaels MD
Ready for crabbing.
Just another day on the Chesapeake.

But now it was our turn — and only two short days in a place meant for longer. What would we do besides relax?

We began at the Chesapeake Bay Maritime Museum where we were greeted by Freedom’s Figurehead — masked as she should be! — that had to be removed from the 88-foot schooner yacht Freedom. Seems this 450-pound adornment fashioned by John M. Cook in 1950 was a bit heavy, so it found a new home here.

Freedom's Figurehead, St. Michaels MD
Freedom’s Figurehead, c.1950 by John M. Cook — as seen at the Chesapeake Bay Maritime Museum, St. Michaels.

The Chesapeake Bay Maritime Museum offers hands-on experiences and real people who share knowledge and experience. But you can also tour the 1879 Hooper Strait Lighthouse and see the Chesapeake from a better vantage point for the same price of admission.

Chesapeake Bay Maritime Museum, St. Michaels MD


With sightseeing behind us, the search was on for great Eastern Shore food. St. Michaels has more restaurants than we had time for, but we listed our priorities: Crabmeat would have to be high on the menu with outdoor seating near the water a close second.

St Michaels Crab and Steak House
Watch the boats go by; dine on crab and steak.
Does it get any better than this?

From St. Michaels Crab and Steak House, we ordered the chef’s special — broiled crabmeat — and took a seat at a picnic table at water’s edge. Who knew a simple concoction of pure lump crabmeat sautéed in butter would make for memorable luxury?

Sauteed crabmeat at St. Michaels Crab and Steak House
Chef’s special at St. Michaels Crab and Steak House

At The Crab Claw on the second night, we watched as two young cooks steamed baskets of crabs and then plopped them onto a platter for good pickin’ and good eatin’ by the guests who could hardly wait.


But it may have been Captain Bryan’s water taxi tour of St. Michaels that gave us the best glimpse of this lovely Chesapeake Bay town. We rode past the Inn at Perry Cabin where guests enjoyed drinks at sundown in white Adirondack chairs.

Inn at Perry Cabin, St. Michaels, MD
Guests relax at sundown at the Inn at Perry Cabin, St. Michaels.

We read names of boats moored at private docks.

Three boats, St. Michaels MD
Halcyon Days, St. Michaels harbor
Someday, St. Michaels MD

And watched the Wednesday Sailboat Races from a distance.

St. Michaels MD Sailboat Races
Wednesday night sailboat races on the Chesapeake Bay.

Saving the best for last, Captain Bryan drove past Hooper Strait Lighthouse just as the sun set on St. Michaels.

Sundown on Hooper Strait Lighthouse, St. Michaels MD

Our destination exceeded expectations, and our only regret was that the time was too short.

Coming up: Look for our next post featuring homes of St. Michaels and a surprise covered bridge!

If you’re even thinking of seeing charming seascapes at every turn of your vacation, book a trip to St. Michaels, Maryland, now. Remember, weekend rooms go fast!

Travel the waterways,

Rusha and Bert

26 thoughts on “Destination reached: St. Michaels, MD — Road Trip 2020

  1. Prior...

    what a helpful post! I will bookmark this for the future e- my brother-n-law lives in MD and this could be a nice place to add to a combined visit
    and the plate of buttered and sautéed crabmeat was a great shot – reminds us that less can b more – and I bet it was so good

    1. Oh, the Places We See

      I have a feeling that any meal in any restaurant in St. Michaels would be good. This wasn’t even a fancy place. But the crabmeat was divine! Your brother has probably heard if St. Michaels. It’s a vacation destination for folks living in Washington DC and Baltimore. Thanks for looking and commenting. I always appreciate your thoughts.

  2. WanderingCanadians

    This coastal town looks absolutely stunning. I love the charming architecture and sailboats. There’s just something about being so close to the ocean that I find so refreshing and calming.

    1. Oh, the Places We See

      We feel the same way. It’s a pretty place steeped in history, but it’s also a seemingly positive environment as well. So many residents went out of their way to be nice and to share their love of St. Michaels. Thanks for taking a look.

  3. Curt Mekemson

    It looks like a delightful little town, Rusha. And your photographs definitely made me want to visit. I noticed it was just off Highway 50, one of the roads that Peggy and I explored on our wandering this past summer. I’ll soon be doing a post on it as it makes its way across Nevada, ‘the loneliest road in America.” Thanks for the tour. –Curt

  4. Toonsarah

    We’ve never been to Maryland on our many US trips but if we do in the future St Michaels will be on our itinerary for sure! I can see that it’s just the sort of place we like – coastal setting, seafood, attractive old houses, and the cottage looks perfect 🙂 I love your last photo in particular!

  5. We Travel Happy

    Oh my gosh, that crab dish! Looks super good. I love crabs. Here in Singapore it’s cooked with chili sauce or black pepper. That town looks so quiet, I’d love to go there too! 🙂

It makes our day to hear from you.