You might not recognize the name St. Michaels, Maryland, but chances are you’ve seen glimpses of this Eastern Shore town in Wedding Crashers. Remember that wedding reception scene at the start of the 2005 movie? That was filmed at the Inn at Perry Cabin, a stunning, award-winning retreat right on the Miles River. But St. Michaels isn’t just a Hollywood backdrop—it’s also famous for tricking the British during the War of 1812. Legend has it, locals hung lanterns to misdirect enemy fire, earning it the nickname “the town that fooled the British.”
Brian Ball, general manager of The Wildset Hotel, says visitors love St. Michaels for its “beautiful harbor, historic charm, and laid-back vibe.” This is the kind of place where slowing down is the norm—whether you’re wandering by the water, browsing the nautical shops on Talbot Street, or digging into fresh seafood (Maryland crabs, obviously).
If that sounds like your ideal getaway, let’s plan your trip. Here’s the best of St. Michaels—where to eat, what to see, and what to do.
Top 5 Can’t-Miss Experiences
- Splurge at the Inn at Perry Cabin for luxury, or go boutique at The Wildset Hotel.
- Sail into sunset on the Selina II.
- Dine at Ruse, where chef Michael Correll (a 2025 James Beard nominee) works his magic.
- Visit between April and November for peak crab season.
- Shop your way through Talbot Street’s boutiques and galleries.
Best Hotels
Inn at Perry Cabin
This is the place to stay in St. Michaels. The historic 1800s property blends maritime charm with modern elegance—think breezy rooms, chic nautical decor (no cheesy souvenirs here), and plenty to do. Bike into town (they’ll loan you one), play croquet or tennis, or just lounge by the marina. There’s even a spa and yoga for total relaxation.
The Wildset Hotel
Fresh from a full 19th-century makeover, The Wildset opened in 2021 and quickly became an Eastern Shore favorite. Minimalist style, prime downtown location, and sweet perks (think s’mores kits, free bikes, and breakfast) make it a standout. Many rooms have private balconies, fireplaces, or soaking tubs—perfect for unwinding.
Things to Do
Explore the Harborfront
“The harbor is St. Michaels’ heart,” says Ball. “It’s got gorgeous views and a rich maritime history.” Even just strolling along is worth it, but for something extra, hop on the Selina II for a sunset sail. “It’s pure magic,” adds Emily Wilhelm from the Inn at Perry Cabin. “Keep an eye out for bald eagles, herons, and dolphins.”
Dive into History
Start at the Chesapeake Bay Maritime Museum—it’s a deep dive into the bay’s past. Then, wander the streets to spot historic homes like the Cannonball House, which (you guessed it) took a hit in the War of 1812.
Take the Ferry
Just a short drive from town, hop on one of America’s oldest private ferries. Ball’s tip: “Ride the Oxford-Bellevue ferry to Scottish Highland Creamery—best homemade ice cream I’ve ever had.”
Stroll Talbot Street
This charming strip is packed with colonial buildings, quirky shops, and top-notch eats (from James Beard chefs to wood-fired pizza). After shopping, hit Lyon Rum and Windon Distilling for free tastings—open daily.
Best Shopping
- Guilford and Company – Ball’s pick for “world-class estate jewelry,” especially Victorian, art deco, and art nouveau pieces.
- Book Hounds – Forgot a book? Grab a bestseller here, or bring the kids for story hour. Look for the bright pink door!
- The Bench Goods – The kind of shop where you’ll leave with something unexpected—maybe a vintage sweater, a logo cap, or fun patches.
Best Restaurants
- Ruse – The Wildset’s restaurant, led by James Beard-nominated chef Michael Correll. Think smoked trout dip, anchovy toast, and spicy tuna handrolls.
- The Crab Claw – A 50-year staple for Chesapeake seafood (like crab cakes and fried crab balls). Closed until April 2025—plan accordingly!
- Ava’s Pizzeria – Family- and dog-friendly, with killer wood-fired pizza and famous meatballs.
- Foxy’s Harbor Grille – Sip an orange crush by the water while eating fried oysters, wings, or fish and chips.
Best Time to Visit
St. Michaels shines year-round, but May through October is peak season. Spring brings blooming tulips and daffodils, summer means perfect water weather and crab feasts, and fall offers crisp air for biking or strolling.
How to Get There
The nearest major airport is BWI (70 miles away). Reagan National is another option (85 miles). If you’re coming from the south or west, you’ll cross the Chesapeake Bay Bridge.
Getting Around
Once you’re there, ditch the car—St. Michaels is super walkable. Ball’s advice: “Comfy shoes are a must.” For longer jaunts, rent bikes from Shore Pedal & Paddle.