Did you know there’s a New England-style destination right on Maryland’s Eastern Shore?
Named one of the “Top 10 Best Small Coastal Towns in America,” by USA Today and “Most Beautiful Town in Maryland,” by Conde Nast, St. Michaels is worthy of a weekend getaway or a romantic staycation.
In St. Michaels, Maryland, history surrounds you. Wander its preserved downtown, lined with gourmet restaurants, boutiques, and wineries. See beautiful federal and Victorian homes and old churches. Step back in time at a local museum then take in sailboat-filled harbor views at a local park. Or, simply have an orange crush overlooking a yacht-lined marina.
Don’t forget about the incredible sunsets the Eastern Shore is famous for. Whether you do a little or a lot here is up to you.
On a recent trip to this captivating Chesapeake Bay haven, we couldn’t help but fall in love with St. Michaels.
Here are some of our favorite places to see, dine, shop, and things to know before you go.
The History of St. Michaels, MD
The oldest town in Talbot County, St. Michael’s, dates back to the 1600s. In 1672, they named it after the first church started there, called the Christ Episcopal Church of St Michael Archangel.
After 340 years, the church continues to serve the community. Today you can visit the 1878 church on Talbot St in the heart of downtown St. Michael. Many of the headstones in its churchyard cemetery are from the 1800s.
St. Michaels is on a peninsula and surrounded by two beautiful Chesapeake Bay-fed bodies of water.
The Miles River is the larger of the two and is to the west. On the river, you’ll find the Chesapeake Bay Maritime Museum, Muskrat Park, marinas, restaurants, and a few hotels. At Muskrat Park, enjoy live music on Thursday nights throughout the summer.
To the east of downtown is the quieter Broad Creek, perfect for kayaking. You can catch views of it from St. Michael’s beautiful Waterfront Park.
Things To Do In St. Michaels, MD
St. Michaels is easy to explore in a day! Its downtown and most points of interest are all within a ½ mile radius.
Most shops and restaurants are found along Talbot Street. For more time to browse shops and relax, plan for at least 2 days. It’s a great place to bring your bike too. Rentals are available, but some hotels like the Wildset offer bikes free to guests.
St. Michaels earned the proud title of “The Town that Fooled the British.” It’s even displayed on the town sign as you drive in.
Legend has it that during the War of 1812, the people of St. Michaels learned the British were sailing into the Miles River. They were getting ready to attack the famous shipbuilding town.
The locals forged a plan. They placed lanterns high in trees so the British would overshoot and miss the town with their cannonball fire. The plan worked, and the British only struck one house, known as the Cannonball House. A private residence, it still stands today.
People have been summering in St. Michael’s since the 1880s. With plenty to do, see and eat, it continues to be a haven for travelers.
Stroll downtown and shop one of the many unique clothing, home décor, or jewelry boutiques. Or get inspired at an art gallery.
Drink a crush cocktail, indulge in crab everything, sample local raw oysters, have a slice of Maryland’s famous Smith Island Cake and a gourmet coffee at Skipjack’s St. Michaels, or cool off with a sundae from Justine’s Ice-Cream Parlour.
For some imported Italian specialties like gourmet pasta, condiments, home goods, and Italian wines, head to Simpatico. Then pop into Olivins for an olive oil and vinegar tasting.
For adult friendly beverages, try locally brewed beers at the award winning Eastern Shore Brewing or St. Michael’s own distilled rum at Lyon Distillery. Wine lovers can try locally grown and produced wines in the tasting rooms at St. Michael’s Winery or Bordeleau Winery across the street.
Nature lovers can relax in one of the many parks, or hike or bike the easy 1.3 mile St. Michael’s Nature Trail that takes you through a covered bridge in Waterfront Park where you can catch stunning views of Broad Creek.
Those wanting to get out on the water can book a local cruise, or rent a kayak to explore the coast.
Getting to St. Michael’s, Maryland
Only 90 minutes from Washington D.C., Baltimore and Wilmington, Delaware and under 2 hours from Philadelphia, St. Michaels on Maryland’s Eastern shore is just off the Ocean Gateway (Route 50).
Those coming by boat can call ahead and have a slip ready at the local marinas or drop anchor in the St. Michaels harbor and catch the Harbor Shuttle water taxi into town. (Call 410-819-9606 or VHF Channel 71)
Parking
Arriving by car: St. Michaels has several public lots with free street parking and immaculate public bathrooms.
Arriving by boat: Dock at a local marina and take a short stroll to one of its waterfront or downtown restaurants.
Places Mentioned
St. Michaels Hotels
The Wildset Hotel
209 N Talbot St, St. Michaels, MD 21663-2103
https://thewildset.com
St. Michaels Dining
Ruse (In the Wildset Hotel)
209 N Talbot St, St Michaels, MD 21663
https://ruserestaurant.com
Bistro St. Michaels
403 S Talbot St, St Michaels, MD 21663
https://www.bistrostmichaels.com
Carpenter Street Saloon
403 South Talbot Street, St. Michaels, MD 21663
https://carpenterstreetsaloon.com
Foxy’s Harbor Grille
125 Mulberry St, St Michaels, MD 21663
https://www.foxysharborgrille.com
Antiques
Antiques on Talbot
211 N Talbot St # 4, St Michaels, MD 21663
https://antiquesontalbot.com
St. Michaels Museums
Chesapeake Bay Maritime Museum
213 N Talbot St, St Michaels, MD 21663
https://cbmm.org
St. Michaels Museum
201 E Chestnut St, St Michaels, MD 21663
https://www.stmichaelsmuseum.org
Classic Motor Museum
102 E. Marengo Street St. Michaels MD 21663
https://www.classicmotormuseum.org
Breweries, Wineries and Distilleries
Eastern Shore Brewing
605 S Talbot St, St Michaels, MD 21663
easternshorebrewing.com
St. Michaels Winery
609 S Talbot St, St Michaels, MD 21663
St-michaels-winery.com
Bordeleau Winery @ St. Michaels
500 S Talbot St, St Michaels, MD 21663
https://www.bordeleauwine.com
Lyon Distillery
605 S Talbot St UNIT 6, St Michaels, MD 21663
https://www.lyonrum.com
St. Michaels Coffee, Ice Cream and Gourmet Shops
Skipjack’s St. Michaels
111 S Talbot St, St Michaels, MD 21663
https://www.facebook.com/SkipjacksMD
Justine’s Ice Cream Parlor
106 N Talbot St, St Michaels, MD 21663
http://justinesicecreamparlor.com
Simpatico
104 Railroad Ave, St Michaels, MD 21663
https://www.simpaticostmichaels.com
Olivins Tasting Room – Aged Infused Fine Olive Oil & Vinegars
110 N Talbot St, St Michaels, MD 21663
http://www.olivinsstmichaels.com
