OUR STORY
Founded in 1672, St. Michaels was a renowned shipbuilding center. From Native American-inspired dugouts to swift Baltimore Clipper schooners, our yards produced the very vessels that drew British fire in 1813, earning us the title "the town that fooled the British." This technical evolution birthed the bugeye—a unique schooner-rigged vessel that became the lifeblood of local watermen. Today, the legacy of skipjacks and log canoes remains the heart of our rich maritime history.
Pictured: The Chesapeake Bay Maritime Museum. Pictured below a historic cannon at Muskrat Park.
SIGNATURE EVENTS
St. Michaels celebrates all year with beloved signature events—from spring waterfront festivals and summer boat shows to vibrant fall traditions and magical holiday gatherings. Each annual event brings locals + visitors together to enjoy the town’s coastal charm.
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A Patriot Wedding
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Miles River
Log Canoe Races
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July 4th Fireworks
+ Big Band Night
LIVE LIKE A LOCAL
Experience St. Michaels the way residents do—favorite restaurants, local shops, scenic walks, & hidden spots that define the town’s coastal charm. Dive into authentic moments that capture the heart of this historic waterfront community.
Pictured: Gina's Cafe + St Michaels is an incredibly Dog-Friendly town.
STAY
Stay invites you to relax in the charm of St. Michaels with boutique inns, waterfront hotels, and cozy B&Bs that capture the town’s peaceful Chesapeake spirit. Find the perfect place to unwind, recharge, and experience the beauty of this historic coastal community.
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The Inn at Perry Cabin
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The Old Brick Inn
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The Snuggery
SHOP
Shop showcases St. Michaels’ diverse boutiques, artisan shops, and galleries filled with coastal style, handmade goods, and thoughtful gifts. Enjoy a relaxed shopping experience that reflects the town’s warm spirit and Chesapeake heritage.
Pictured:
Window shopping at DBS Fine Jewelry.
Pictured: The Bench
EAT+DRINK
Eat + Drink highlights St. Michaels’ diverse dining scene—from dockside seafood and gourmet cuisine to charming cafés and craft cocktails. Savor fresh flavors, local ingredients, and memorable meals inspired by the Chesapeake Bay.
Pictured: Oysters on the half shell
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Bistro St. Michaels
Pictured:
Lyon Rum // Windon Distilling
SEE+DO
See + Do invites you to discover St. Michaels through scenic walks, boat tours, museums, artisan shops, and outdoor activities. Whether relaxing or exploring, you’ll find memorable experiences shaped by the town’s coastal beauty and history.
Pictured: Lady Patty / Sailing Charters
St. Michaels Museum
