16 Best Things To Do In St. Michaels, Maryland

The best ways to spend your time in “the town that fooled the British.”

The beating heart of Maryland’s Eastern Shore, this nook of a town on the Chesapeake Bay has an individual spirit steeped in maritime history. At once a languid small town full of charm and a bustling vacation town within an hour and a half drive from Washington, D.C., St. Michaels positively shines in the summer. Rich in history (the town was founded way back in 1677) and proud of its nickname as “the town that fooled the British” in the War of 1812, St. Michaels is also known, of course, for its Maryland crabs, the season of which runs April through November. The charming, walkable downtown is lined with Victorian buildings now housing local shops and outfitters. Although it does put on a stunning show in the summer, St. Michaels is the quintessential Eastern Shore getaway anytime of the year.

What To Do

Learn About the Area’s History

St. Michaels and the surrounding area are rich in history and have centuries' worth of stories to tell. The compact St. Michaels Museum centers its exhibits on 19th-century local history and offers excellent historic walking tours, including a tour offered the first Saturday of every month that explores Frederick Douglass’ three years in St. Michaels.

stmichaelsmuseum.org, 201 East Chestnut Street, St. Michaels, MD 21663

Examine Maritime Artifacts and Vessels

Head to the waterfront Chesapeake Bay Maritime Museum for an overview of hundreds of years of St. Michaels history through a rich collection of Chesapeake Bay artifacts, exhibitions, and vessels. The museum offers a host of public programs and workshops, including the Apprentice for a Day Shipyard Program for the curious of all ages.

cbmm.org, 213 North Talbot Street, St. Michaels, MD 21663

Window Shop

St. Michaels is a town made for strolling and South Talbot Street, which runs the length of the village, is where you should begin. Olde Town Candy Company, The Preppy Redneck, Chesapeake Trading Company, and The Shops at Sea Captain’s Cottage are town mainstays.

Head Out On the Water

No trip to the Eastern Shore is complete without heading out on the Bay. Sail Selina II offers a wealth of options for enjoying and exploring the Chesapeake, from two-hour day-time water tours, to wine and beer tastings on the water, to moonlit sails, to private charters. Their guides are equally schooled in history and safety, and provide in-depth context for your visit to St. Michaels and the wider Chesapeake Bay region.

sailselina.com, 101 North Harbor Road, St. Michaels, MD 21663

Pedal Your Way Around Town (and Beyond)

Why walk when you can bike? Cruiser bikes provide the perfect mode of transport for exploring the town and the waterfront. For an extended bike adventure, pedal your way to the Oxford-Bellevue Ferry, and board the historic vessel (it’s believed to be the nation’s oldest privately operated ferry) for a 10-minute ride across the Tred Avon River. Many local hotels have bikes available for guests; Shore Pedal & Paddle offers rental options as well.

shorepedalandpaddle.com, 500 South Talbot Street, St. Michaels, MD 21663

Grab a Bite in Oxford

In Oxford, sit fireside at the quaint Robert Morris Inn and order the Smoked Bluefish Pate Crostini. The seafood-forward Capsize OXMD offers waterfront views, cocktails, and appetizers like Jumbo Lump Crab Balls and Crab Cocktail. Follow up with handcrafted ice cream scoops and sundaes at Scottish Highland Creamery. With 600 flavors in rotation, visitors will always find something new.

robertmorrisinn.com, 314 North Morris Street, Oxford, MD 21654

capsizeoxmd.com, 314 Tilghman Street, Oxford, MD 21654

scottishhighlandcreamery.com, 103 South Morris Street, Oxford, MD 21654

Pamper Yourself at the Spa at Harbour Inn

Enjoy a couple's massage or book some solo time at the Spa at Harbour Inn. Services include hot stone massage, paraffin hand and foot treatments, seasonal facials, body scrubs, and wraps. Extend your relaxation with an overnight stay at the Harbour Inn. Many rooms and suites are appointed with private balconies overlooking the harbor. Dine on-site at the inn’s Harbour Lights restaurant with water views, sit poolside, or tour the area on hotel bikes.

spaatharbourinn.com, 101 North Harbor Road, St. Michaels, MD 21663

Where To Eat

Enjoy Oysters at Ruse

Ruse, located in hip The Wildset Hotel, takes its name for the legendary trick the people of St. Michaels used to save the town from a British invasion in the early 19th century. Serving as both a touch point for hotel guests and a meeting place for locals, the restaurant’s menu is Chesapeake Bay-centered and features an impressive list of oysters from up and down the East Coast.

ruserestaurant.com, 209 North Talbot Street, St. Michaels, MD 21663

Order Bottomless Mimosas at The Galley

Down South Talbot Street, The Galley is what small-town restaurant dreams are made of: lively dining rooms and a line out the door on weekend mornings. The restaurant serves bottomless mimosas every Sunday and partaking in the celebration is practically a rite of passage here. The menu includes cold-pressed juices, local handmade crabcakes bene, omelettes, and a maple waffle sandwich. The 1806 building also is home to a popular top-floor Tree Top Lounge which is a local favorite spot to grab a post-dinner drink.

thegalleysaintmichaels.com, 305 South Talbot Street, St. Michaels, MD 21663

Feast on Seafood at The Crab Claw

For a quintessential Maryland seafood experience, head to The Crab Claw. The waterfront restaurant is a relaxed, decades-old, come-as-you-are institution. Get your fill of fresh seafood here–there are plenty of dishes to try, like Oysters Casino, Maryland Crab Soup, steam buckets, and sandwiches. For traditionalists, crabs with Old Bay seasoning are the thing to order.

thecrabclaw.com, 304 Burns Street, St. Michaels, MD 21663

Savor a Casual Meal at Foxy's Harbor Grille

Foxy’s Harbor Grille is another great, local-approved casual dining option serving Caribbean-style dishes, seafood, handhelds, and specialty cocktails. Located in the St. Michaels marina, this spot has some of the best waterfront views and a deck that's perfect for warmer weather.

foxysharborgrille.com, 125 Mulberry Street, St. Michaels, MD 21663

Reserve a Table at STARS

For an upscale dinner, or special occasion, head to STARS at the Inn at Perry Cabin, which seats guests both in their dining rooms and also arranges private, waterfront tables. The three-course tasting menu changes daily and draws heavily from what’s in season—crabs, oysters, lobsters, as well as local produce.

innatperrycabin.com/dining/stars, 308 Watkins Lane, St. Michaels, MD 21663

Where To Drink

Get a Pint at Eastern Shore Brewing

Before or after dinner, stop in for a beer at Eastern Shore Brewing. Selections range from seasonal beers, flights, and growlers to go. Enjoy events like live music and trivia throughout the week. Try the St. Michaels Amber Ale, their flagship beer.

easternshorebrewing.com, 605 South Talbot Street, St. Michaels, MD 21663

Sample Spirits at Lyon Rum

Visit the Lyon Rum distillery to learn about the small-batch process, taste their signature and seasonal American rums, and purchase some to take home with you. Rum liqueurs like Coffee Rum and Curacao Orange are infused by hand, and their rums are distilled in traditional pot stills using Louisiana cane sugar.

lyonrum.com/visit-the-distillery, 103 East Marengo Street, St. Michaels, MD

Where To Stay

Stay in the Historic Inn at Perry Cabin

The historic Inn at Perry Cabin looms large in St. Michaels. The classic resort went down in film history for being part of the cult-hit movie Wedding Crashers, but today guests will find a stay here an elegant, peaceful, and secluded affair. The Inn boasts 26 acres of gardens, orchards, lawns, and shore. Its restaurant, as well as a highly regarded spa and golf course, keep guests returning year after year.

innatperrycabin.com, 308 Watkins Lane, St. Michaels, MD 21663

Relax in Style at The Wildset Hotel

The Wildset Hotel, a Scandinavian-chic boutique hotel stretched across four 19th-century buildings, burst on the scene in 2021 and places you centrally in the buzz of the town. Breezy modern rooms, firepits, and its Chesapeake-centric restaurant make this a standout.

thewildset.com, 209 Talbot Street, St. Michaels, MD 21663

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