The Ultimate Guide: Best Things to Do in St. Michaels, MD

St. Michaels, Maryland, is one of the prettiest places for a day trip or weekend trip from Washington, DC.  It’s about a 1.5-hour drive from the District on Maryland’s Eastern Shore, and it oozes coastal charm.  If you are looking for classic East Coast summer vibes, St. Michaels has it by the boatload with water views, classic seafood restaurants, and walkable streets.

Here are some historical facts about St. Michaels before it became a tourist destination:

• St. Michaels shipwrights were famous for designing and building “Baltimore Clippers”—incredibly fast, sleek schooners that could easily outrun heavy British naval vessels. The town used these ships heavily as privateers during the War of 1812, making it a vital asset to the American war effort and a major thorn in the British military’s side.

• St. Michaels was defined by the oyster and crab industries, with large packing houses lining the Miles River. Fleets of traditional sailing workboats like skipjacks and bugeyes dredged the bay for oysters, shipping them rapidly to restaurants in Baltimore and beyond. 

Best Time to Visit St. Michaels, MD

Late spring to early fall are great times to visit this small town in Maryland.  If you want typical New England summer vibes, go in the spring for cooler weather.  If you enjoy Maryland’s hot and humid days, then go in the summer months.  For classic fall charm, head to St. Michaels in early fall.

The Best Things to Do in St. Michaels, MD

St. Michaels, MD is a relaxing destination with a slow pace.  It’s a great way to unwind away from the city.

If a slow day is up your alley, here are some things to do in St. Michaels at a leisurely, relaxed pace.

Take a Boat Trip

St. Michaels is on the water; after all, it’s a harbor town.  So one of the best things to do in St. Michaels is to experience the town from the water.  

There are a few options for a boat tour in St. Michaels.   

Patriot Cruises

Patriot Cruises is the most popular water experience in St. Michaels.  With this boat tour you get a narrated history while cruising down the Miles River on a 65-foot, USCG-inspected vessel built to resemble a traditional Chesapeake Bay steamboat.  During the boating season from April to November, Patriot Cruises departs from St. Michaels harbor at the Chesapeake Bay Maritime Museum. Free parking is available in CBMM’s lot.  Depending on the day the cruise departs at 12:30 pm or 2:30 pm and ranges in price from $5 per person to $30 per person based on age.

Private Cruise

A private boat charter is another option to experience St. Michaels from the water.  This is a great idea for a birthday or celebration!  Boat rentals start at $400 per hour.   A sunset cruise is also a great option.  https://www.smharborshuttle.com/st-michaels-party-boat-1

Sailing

A sailing boat is another option if you are up for an adventure.  Sailing boats start at $95 per person.   https://www.stmichaelssailingcharters.com/sailing-trips/2-hour-chesapeake-day-sails/

Kayaking

If you want to get a workout in, then kayaking is a great way to have a day on the water.  Kayak rentals start at $60 for a half day.  https://www.smharborshuttle.com/shore-pedal-paddlerentals

Have Drinks and Seafood at St. Michaels Marina

You can’t leave St. Michaels without a stop at the Marina, and not just to get on a boat.  The views are incredible, with a variety of restaurant options.  Foxy’s is a classic East Coast beach bar.  Grab an orange crush here.  Eat Maryland Blue Crabs at the Crab Claw, a local institution since 1965!  They serve up an authentic crab-picking experience right on the docks. Grab a wooden mallet, order a half-bushel of Maryland blue crabs dusted with Old Bay, and enjoy the waterfront views.

Relax at Muskrat Park

If you want to enjoy a place to sit on the water without having to buy food or drinks, Muskrat Park is the spot.  It is right on the water; there’s even a bench.  But you can totally bring a book and throw down a blanket for a little picnic or just to do some reading in the sun.

Window Shopping on Talbot Street 

Talbot Street is lined with cute little shops and is perfect for a stroll plus window shopping.  Go to the Bench and design your own patch sweater.

Bike Around Town

There’s no better way to see a small town than renting a bike!  Biking is a great way to see all the cute houses around the town.  Be careful, though; soon you’ll be calling your real estate agent on how you can own a house in St. Michaels!

Scenic Ferry Oxford-Bellevue

The Oxford-Bellevue Ferry is America’s oldest privately owned ferry, continuously operating since 1683!  For just $20, score a ride with your car across the Tred Avon River between historic Oxford and Bellevue, Maryland.  Passage travelers have taken this route for over three centuries.  Explore Oxford and stop by Doc’s Sunset Grille for sunset dinner and a drink.

The Chesapeake Bay Maritime Museum

No trip to St. Michaels is complete without a visit to the Chesapeake Bay Maritime Museum. Spread across an 18-acre waterfront campus, this museum preserves the the area’s nautical roots.   

Must-Sees at the Museum:

• The Hooper Strait Lighthouse: Climb to the top of this iconic 1879 lighthouse for stunning panoramic views of the harbor.   
• Working Shipyard: Watch master shipwrights restore historic wooden boats in real-time.
• Historic Fleet: Step aboard traditional skipjacks and bugeyes that once dominated the bay’s oyster dredging industry

Explore the Grounds at the Inn at Perry Cabin

Inn at Perry Cabin is known as the set for the movie Wedding Crashers.  The property is absolutely gorgeous.  It is a luxury hotel with rooms starting at $550 per night.  But if their accommodations are out of your price range, you can still visit the property.  

Stop by their restaurant STARS for coastal cuisine on the Miles River.  Brunch is delicious here!  Have a stroll through their gardens; it’s stunning. 

St. Michaels, MD FAQs

How long should I stay in St. Michaels?

St. Michaels is a perfect day trip if you live in DC, Maryland, or Virginia.  But if you want to experience all the activities a Friday through Sunday trip is perfect.

How do you get to St. Michaels?

St. Michaels is easily accessible by car from major airports in the area, including BWI, DCA, and IAD.

Is St. Michaels dog friendly?

Yes, it is!  Everyone had their dogs with them, including me!

Is there a beach in St. Michaels?

St. Michaels does not have a beach, but there are a few beaches not far away on the Chesapeake Bay, such as Claiborne Beach.