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!

Lodging
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.


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.

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.
Dining
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.

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?
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.
Touring
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.

We read names of boats moored at private docks.




And watched the Wednesday Sailboat Races from a distance.

Saving the best for last, Captain Bryan drove past Hooper Strait Lighthouse just as the sun set on St. Michaels.
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
travelgarb
It looks like a lovely place!
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
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.
Prior...
I will keep you posted if we visit !!
Oh, the Places We See
Great! Thanks.
pam@ichoosethis
You continue to make me green with envy with the boats!! And those crabs look pretty delish.
Oh, the Places We See
Boats and crabs. Doesn’t get much better than that!!
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.
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.
Anonymous
One of my favorite places, too!
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
Oh, the Places We See
Would love to travel Hwy. 50. Cant wait to see what you found. The Eastern Shore has a charm all its own — and very different from the Oregon Coast. I’m ready to go again!
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!
Oh, the Places We See
Thanks for your lovely comments. I think you’d enjoy a stay at St. Michaels. And there’s shopping, too. I just don’t take pictures this time.
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! 🙂
Oh, the Places We See
The crab dish was a simple one – just broiled with butter. But so good. An indulgence.
We Travel Happy
It is, isn’t it? And we can’t have it too often.
anbaworldwide
Looks so charming and sounds like you had a great time.
Oh, the Places We See
It’s a classy little town in a beautiful spot on the Eastern Shore. We enjoyed what little time we had there.
anbaworldwide
Even little is definitely better than none 🙂
tappjeanne
one of the places I want to go! Thanks for the virtual tour
Oh, the Places We See
It’s definitely a pretty place!!!
Ingrid
Looks and sounds like a lovely vacation spot. I’m always entertained by boat names and curious about the stories behind the name.
Oh, the Places We See
We are as well. The name Someday was most intriguing!!
Nancy Stanley
What a picturesque town!!! And the sight of that crabmeat dish! 😋
Oh, the Places We See
That was a lot of crabmeat — and I ate it all. We love St. Michaels. But I guess this was our last trip. A lot of folks from Washington and Baltimore vacation there. You can see why!