A Bayside Escape – Chesapeake’s St. Michaels

Stories and photos by Roxie LaFever (unless otherwise indicated)

The Laid Back Vibe in St. Michaels on the Chesapeake

That Laid-Back Chesapeake Feel in St. Michaels in Chesapeake Bay in Maryland
That Laid-Back Chesapeake Feel in St. Michaels

Feeling the wind in my hair as my legs dangle over the edge, the water rhythmically sloshing the pilings below me, I let out a sigh of relief and feel the stress melt away.  I have escaped from the DC suburbs to a small town across the Bay Bridge.   Yes – it is Chesapeake time. 

While some may be drawn to Annapolis, I wanted to get away – socially distanced in a more laid back and relaxing way.  I was in search of fresh seafood, historic sites, a small-town feel, strollable streets, and a bit of rest and solitude.  Remembering St. Michaels from a prior trip, it beckoned me for a repeat performance.

Sitting on the Dock of the Bay in Maryland

I could not have picked a better time to visit this beautiful corner of Maryland.  It is quiet but not deserted and they take their pandemic face mask-wearing seriously – it is mandatory throughout the town.  Being October, the summer visitors have gone home, boats are stored, and yet the locals or distantly local (from an hour away) like me, know it is the perfect time of the year to visit.  The weather ranges from 60 to 80 degrees and it is perfect to stroll, eat, drink, and shop.  Hum along – yes, that song – as we explore this small town on the Chesapeake Bay in Maryland.

The Quiet Solitude at the End of the Dock at Navy Point in Chesapeake Maryland
The Quiet Solitude at the End of the Dock at Navy Point
Looking Across the Inlet of Gorgeous Blue Water Bring Peace and Tranquility
Looking Across the Inlet of Gorgeous Blue Water Bring Peace and Tranquility

Surrounded by History – Here are a Few Highlights

St. Michaels, named after Archangel Michael, was established in 1672 as an Episcopal Parish.  While St. Mary’s was the first British settlement in what became Maryland, it was closely followed by St. Michaels, where locals easily lived off the Bay as tradesmen offering oysters and crabs, or building the ships needed to collect them.  Farmers also tilled the lands and tobacco became another significant trade. The Chesapeake Bay Maritime Museum offers a historical perspective and has relocated old ships/vessels, historic homes and buildings from Saint Mary’s, and has a lighthouse from the bay to explore during your visit.

The Museum’s current project is the building of a replica of the Dove – one of two ships used by the British when they settled this area in the 17th century.  Sailing together, known as the Ark and the Dove, the Dove was the smaller ship, able to handle 42 tons.  A prior replica of the Dove was constructed for Maryland’s 350th Anniversary and was commissioned in 1978.  That replica was also used extensively to represent the Mayflower in the 1979 “made for TV film” of the same name.  While St. Michael’s Dove has been delayed a bit (see photo), they still have plans to complete it by late 2021.  Please stop by, as the shipbuilders welcome the opportunity to talk about their project.  

1978 Dove Replica By Acroterion - Own work, CC BY-SA 3.0
1978 Dove Replica By Acroterion - Own work, CC BY-SA 3.0
Progress at Chesapeake Maritime Museum with Plans to Finish their Dove Replica in Late 2021 in Maryland's Chesapeake Bay
Progress at Chesapeake Maritime Museum with Plans to Finish their Dove Replica in Late 2021

Star Spangled Banner National Historic Trail on Chesapeake Bay

This is also a great place to learn about the War of 1812 by following the Star Spangled Banner National Historic Trail.  Note their website is www.starspangledtrail.net for more information.  Specific to St Michaels, the story is told about how the town was saved by the locals one morning in 1813 when an early warning was received that the British were sailing up the River intending to shell the town.  After evacuating most of the inhabitants in this Maryland seaside town, a few hung lanterns in treetops outside of town and extinguished all lights in St. Michaels.  The British were fooled and ended up missing most dwellings and the town’s people were able to return unharmed.

Make History Come Alive on the Historic Trail of the War of 1812 including Star Spangled Banner
Make History Come Alive on the Historic Trail of the War of 1812

Frederick Douglass was Born Into Slavery

Frederick Douglass Historical Marker of His Humble Beginnings birthplace
Frederick Douglass Historical Marker of His Humble Beginnings

This is also the county where Frederick Douglass was born into slavery.  While being shuffled from owner to owner as a child, he taught himself how to read and write and began educating others.  His path led him to become an outspoken abolitionist in Massachusetts and New York, where he succeeded in freeing many slaves.  As a writer and orator on social reform issues, he gained the respect of others and became a statesman, a newspaper publisher, and author of several books.  His place in history demonstrates how a single individual can truly make a difference.

Where to Play in St. Michaels on Chesapeake Bay

The main attraction at the Maritime Museum is the 1879 Hooper Strait Lighthouse.  Unlike the typical tall free-standing lighthouse, the Hooper Strait was one of four surviving Chesapeake Bay hexagonal screw-pile lighthouses.  It screwed into pilings out to sea rather than being land-based.  First set up in Dorchester County back in 1879, it was manned until 1954 and later relocated to St. Michaels.  Touring the inside shows the close living quarters, including a small kitchen and sleeping arrangements at that time. 

Just a few feet away, the Patriot offers historic cruises of the Bay, with as many as 20,000 passengers a year.  Designed in 1989, it resembles a steam ferry that would have been used to transport passengers from Baltimore to St. Michaels back in the day.  The U.S. Coast Guard inspects the vessel, which can carry up to 149 passengers and five crew.

Imagine Manning This Lighthouse 24 hours a Day on Chesapeake Bay in Maryland
Imagine Manning This Lighthouse 24 hours a Day
Patriot Cruises has been Safely Offering Historic Tours of the Chesapeake Bay for 50 Years
Patriot Cruises has been Safely Offering Historic Tours of the Bay for 50 Years

Strolling along St. Michaels Main Street Shopping

Souvenirs, antiques, and local arts and crafts are available at the Museum Shop, or scattered along the main street – known as Talbot.  Since this is a small town on the Chesapeake Bay, most items tend to have either a nautical or homemade essence but offer good quality, and any item will bring back great memories from this trip. 

Discovery Map for St. Michaels Streets and Shops Available at Visitor Center
Discovery Map for St. Michaels Streets and Shops Available at Visitor Center
Souvenirs from the Maritime Museum Store on the Chesapeake Bay
Souvenirs from the Maritime Museum Store
Antiques and Shore Décor from the Sea Captain’s Cottage in Maryland
Antiques and Shore Décor from the Sea Captain’s Cottage
Local Artwork on Display in Shop Windows Along Talbot Street on Chesapeake Bay
Local Artwork on Display in Shop Windows Along Talbot Street

Where to Eat in St. Michaels

After all that walking in this iconic Maryland town, it is now time to find something to eat, and the options are endless.  Whether you want to hammer away at crabs along the side of the dock at the Crab Claw Restaurant (bibs provided), or you like your fresh seafood with an Italian flare like the mussels and clam appetizer I had at Limoncello, you’ll find plenty of great seafood from Chesapeake Bay.  Or sink your teeth into a nice American staple – the burger – at the local saloon at the corner of Carpenter and Talbot Street, along with a nice pint.

Hammer on a Dozen Crabs at the Crab Claw Restaurant in Maryland
Hammer on a Dozen Crabs at the Crab Claw Restaurant
Highly Recommend My Appetizer at Limoncello for Fresh Seafood with an Italian Flair on Chesapeake Bay
Highly Recommend My Appetizer at Limoncello for Fresh Seafood with an Italian Flair
Pull Up a Bar Stool at the Carpenter Street Saloon for a Pint and Burger, crab, or lobster in Maryland's seaside
Pull Up a Bar Stool at the Carpenter Street Saloon for a Pint and Burger

When it is time for Happy Hour, enjoy the local libations conveniently located in one town block.  Both St. Michaels Winery and Eastern Shore Brewing offer plenty of outdoor seating next door to each other.  Around back, find Window Distilling, with an outdoor bar set up for easy access to hard liquors distilled onsite.  So, pull up a chair, get samples, tasting flights, or a bottle and enjoy as the sun sets on this wonderful day on the Chesapeake.  Or spend the weekend and pick up something to take back to your room.

Eastern Shore Brewing with Outdoor Seating to the Left to eat and drink
Eastern Shore Brewing with Outdoor Seating to the Left
St. Michaels Winery with Outdoor Seating to the Right for wine and food on the Chesapeake Bay in Maryland
St. Michaels Winery with Outdoor Seating to the Right
Window Distilling for Easy Pickup at the Bar Behind for whiskey and bourbon
Window Distilling for Easy Pickup at the Bar Behind

Where to Stay in St. Michaels

St. Michaels deserves more than a day trip, so think about spending a weekend.  A couple of accommodations to check out would be the Inn at Perry Cabin, which is located along the Miles River, and is surrounded by 26 acres of forest and farmland.  In a casual and relaxing environment, visitors can also play tennis on the green-clay courts or tee off at their new 18-hole Pete Dye designed golf course.  They take pride in offering locally raised meats and poultry and fresh produce as well as oysters from the oyster-farm next door in their restaurants.  Oh – and do not forget the spa.

Another option on this Maryland road trip would be the St. Michaels Inn on the way into town.  While not offering all the amenities of the Inn at Perry Cabin, it feels more like home, has the convenience of being close to most of St. Michaels, and will not leave a dent in your wallet either.

Inn at Perry Cabin Offers Acres of Exploration and Fun is a great place to stay in St. Michael's
Inn at Perry Cabin Offers Acres of Exploration and Fun
St. Michaels Inn Offers Easy Access to Everything and is an excellent place to stay in St. Michaels
St. Michaels Inn Offers Easy Access to Everything

Come Enjoy the Laid Back Attitude of St. Michaels

After spending a day or weekend in St. Michaels, to unwind plan to return throughout the year for other seasonal activities on Chesapeake Bay.  Take a look at the town’s website – www.stmichaelsmd.gov – where you’ll also find a list of 50 Free Things To Do.  And we’ll leave you with one last photo about attitude….if it starts to dip….it is time to return to St. Michaels for another adjustment.

Maintain that Bay Attitude with crab, lobster, beer, and whiskey in St. Michael's
Maintain that Bay Attitude

Based in the Washington, DC metropolitan area, Roxie LaFever likes her town but knows she needs to explore the world and search out her own truth.  Without creating even an “unofficial bucket list,” she’s been to all 7 continents, seen all 7 Wonders of the World and over 40 countries. With each trip – she tries to identify a way to step out of her comfort zone – and grow.  Whether she’s jumping off a mountain in Rio to hang-glide down to the beach, exploring the world’s largest waterfalls by ultra-lite or zodiac, hiking at high altitudes in Bhutan and Peru, or doing the “Walk of Faith” on the world’s longest glass bridge in China, you’ll want to travel along.  In addition to freelance travel writing and photography, Roxie manages a lifestyle and travel blog at www.RoamingwithRoxie.com.