Packed Suitcase | Things to Do in St. Michaels, Maryland
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Things to Do in St. Michaels, Maryland

Things to Do in St. Michaels, Maryland

Welcome to St. Michaels!

St. Michaels, Maryland (the “Hamptons of the Chesapeake”) is where the elite goes to spend the weekend. Located right along the Old Line State’s craggy coastline, it’s an idyllic waterfront retreat where all roads lead to the water. With a deep history and a familiar, small-town feel, it’s the perfect spot for a weekend getaway.

Here are the top things to do in St. Michaels:

Take a Walking Tour
During the warmer months, this 1 1/2 hour Docent-led tour ($10) is the best way to get familiar with the town’s most notable sites in the historic center. Leaving from the St. Michaels Museum at St. Mary’s Square, the tour hits all the main sights and personal stories are interwoven with folklore, historical facts and information about their most famous resident, Frederick Douglass.

St. Michaels Walking Tour


Head Out on the Water
With the sparking water staring you down at every turn, it’s hard not to feel the instinctive urge to get out on the Bay. Luckily, there are tons of options, from harbor tours, sailing and yacht charters, kayaking excursions and more. My favorite? A ride on the traditional historic H.M Krentz skipjack. Here’s a video of my experience:


Take a Bike for a Ride
Besides walking, bikes are the 2nd most used form of transportation in St. Michaels. It’s completely ordinary to see neat little rows of bicycles with baskets in front of every hotel and major establishment. All along the streets, families ride leisurely… the cheery “ding, ding!” of their bells sounded in greeting to friends met along the way. Most B&Bs offer free bike access as part of the room rate, which makes it super convenient for weekend visitors.

Bikes everywhere


Stay at a B&B
The are “hotel towns” and there are “B&B towns.” St. Michaels is decidedly a “B&B town.” At every turn lies a charming inn with a story or two to tell to their guests. My favorite? The Five Gables Inn & Spa. Three historic 19th century homes in the center of town make up a little B&B village. The rooms are quaint and comfortable, the bathrooms feature both a shower and a luxurious whirlpool tub and some rooms have a balcony with two white Adirondack chairs. The generous complimentary breakfast and on-site Aveda spa adds a little something extra to make this the best B&B lodging in town.

5 Gables Inn


Wine and Dine
Even the most discerning foodies will find restaurants and boozy experiences to please the palate and tingle the tastebuds! Here are some standouts:

Ava’s: A pizzeria and wine bar. Start with an appetizer portion of their meatballs. $3 per ball, a little casserole dish comes out piping hot with a perfect meatball covered in tangy marinara sauce with heaps of melted mozzarella and provolone cheese. Pick a wood-fired pizza of your choice, and wrap your delicious meal up with one of their freshly backed cupcakes.

Ava's- pizza

Big Al’s Market: This roadside carry-out cafe has the personality of a place that’s been around for years. With a smoking BBQ grill going out front, passersby are drawn in like a moth to a flame. The fried crabcake sandwich was dually crispy and tender, and the roll slathered with tartar sauce was the ideal accompaniment.

Big Al's Market

Crab Cake from Al's

St. Michaels Winery: The formidable tasting room features wine-barrel tables, warm colors and a very relaxed environment. Some of my favorite varieties include: St. Michaels White (light, nicely balanced, tart), Island Belle (Sangiovese, oaky) and their Chocolate Zin (sweet with a subtle chocolate scent).

St. Michael's Winery

Eastern Shore Brewery: 5 x 5 ounce samples for $10. Good beer. ‘Nuff said.

Eastern Shore Brewery


Take the Oxford-Bellevue Ferry
For a little day trip, take a 10 minute ferry ride across the picturesque Tred Avon River to the quaint town of Oxford. Have lunch at the tavern at the Robert Morris Inn, a grand and welcoming establishment that’s been around since 1710. (Tip: Be sure to get a side of the blue cheese apple cole slaw… it’s a stand out, complete with big chunks of creamy blue cheese.). And, save room for dessert at the nearby Scottish Highland Creamery. As you walk throughout the town, you’ll notice a British trend… Oxford has the Tred Avon River, the Strand… and an authentic black cab car– with a right-handed driver and all!

Oxford Bellevue Ferry


A Night Out in Easton
If you’re looking for a little more hustle and bustle for your getaway, head on over to nearby Easton. A quick 10 mile drive drops you off right in the center of town. Start your night with a pre-dinner cocktail at the historic Tidewater Inn, head over to the iconic Mason’s for a gourmet meal, then catch a show at the Historic Avalon Theatre. Just like that, you’ve got yourself a fun evening out on the town!

Dinner at Mason's

Dinner at Mason’s

A night out at the Avalon Theatre

A night out at the Avalon Theatre


Breakfast at the Inn at Perry Cabin
You can’t visit St. Michaels without stopping in to see the Inn at Perry Cabin, an exclusive resort owned by the Orient-Express company. It’s the only waterfront resort in St. Michaels and utilizes every possibly opportunity to showcase the magnificent views. Needless to say, it is four star luxury to the extreme. But you don’t need to stay here to get a chance to sneak a peek. Make a reservation for breakfast at Sherwood’s Landing, an airy sunroom overlooking the water, and live like the upper crust… if only for a meal.

Inn at Perry Cabin - exterior



**DISCLAIMER: Many of my meals, activities and accommodations for this trip were provided by the Talbot County Office of Tourism. I worked closely with my contacts there to customize an itinerary that best fit my travel perspective and all opinions are my own.**

  • Anne Puspoki
    Posted at 09:43h, 20 April

    Is there a day spa in St. Michael’s or Easton?

    • Christina Ricchiuti-Dubin
      Posted at 19:39h, 25 April

      I haven’t been, but I think you can’t go wrong with a spa treatment at the Inn at Perry Cabin!