After crossing the Chesapeake Bay Bridge, follow U.S. Route 50 down the Delmarva Peninsula and hook west along the scenic stretch of Route 33 to stumble upon Maryland’s coastal cottage town of St. Michaels. Part of the beauty of this idyllic destination – just a 1.5-hour drive from D.C. – is its postage-stamp size. Between the main dining-dense drag of Talbot Street to cute cobblestone side streets leading the way to water, soaking up the picturesque harbor’s top attractions in one weekend — or simply 24 hours — is easy as pie.

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For an on-brand Maryland arrival

It wouldn’t be a trip to the Eastern Shore without waterfront orange crushes and blue crabs, so why not dive right in with both. At trusty boater bar Foxy’s Harbor Grille (125 Mulberry Street), order the fresh-squeezed seaside staple by the bucket and Chesapeake’s star crustacean all kinds of ways (crab cakes, soup, sandwiches, and chilled claws). For the ultimate crab-cracking, Old Bay-blasted experience, 60-year-old seafood house The Crab Claw (304 Burns Street) is the move. Trays topped with steamed crab stay in season here through October. To quench post-picking cravings for beer, head to local pioneer Eastern Shore Brewing (605 South Talbot Street) to sample its award-winning St. Michaels Amber Ale flagship in an old-world setting. Sip and stay on its gravel-lined patio or grab a growler and take the party to-go.

Lodging

The heart of St. Michaels upped its laid-back luxury game in summer 2021 with the anticipated arrival of the Wildset — a stylish, 34-room boutique hotel where a check-in desk doubles as a hip cafe with Ceremony espresso drinks scribbled on a big brown paper roll next to a well-curated sundry shop. Settle into the nautical-chic sanctuary fit for Vogue by flicking on a matte fireplace and relaxing on a private balcony or porch with a read from the room. Complimentary guest perks include custom bikes to roam around town and an abundant breakfast spread full of fresh pastries, coffee, and yogurt. Stroll around its well-manicured grounds and lounge around a stone-framed fire pit at twilight to toast s’mores over a glass of wine. 209 Talbot Street

How to Plan a Perfect Weekend Getaway to St. Michaels, Maryland

Other options: For the ultimate overnight splurge, there’s the luxe Inn at Perry Cabin. Made famous by the movie Wedding Crashers, the postcard-perfect resort with a golf course, pool, spa, and bocce courts is home to special-occasion spot Stars Restaurant. 308 Watkins Lane

Activity interlude: Hit the waterways and rent kayaks or paddleboards from Shore Pedal & Paddle, with pickup points from San Domingo Creek and St. Michaels Harbor.

Aperitivo hour

A surprise slice of the Italian coast lies right off the main drag. Naples natives run nearly decade-old standby Limoncello (200 S. Talbot Street), where Italian wines pour freely from a cheery bar alongside a daily lunch-and-dinner selection of homemade pastas and char-grilled flatbread. To stock up the room (or trunk) with bottles of hard-to-find varietals, along with all-imported Italian cheeses, ceramic plate ware, and jewelry, check out charming retail store Simpatico (104 Railroad Avenue), which now hosts a restaurant pop-up on Saturdays full of seafood stew and eggplant Parm. For more European feels in the center of St. Michaels, consider French-themed Bistro (403 S. Talbot Street). Established in 1995 and reinvented in recent years, the cozy stalwart is the spot for steak frites, tuna nicoise salads, and mussels. During happy hour (4:30 p.m to 6 p.m.), enjoy $8 martinis, $9 lemon vodka-infused cosmos, and a smaller portion of its famed mussels.

Dinner

The team behind Nashville’s award-winning Henrietta Red brought the strip a chic, seafood-centric American restaurant in summer 2021 with the debut of Ruse at the foot of Wildset. A bright and airy raw bar wrapped in hand-painted terracotta tile swaps customers’ pencil-checked shellfish sheets for shucked oysters sourced from nearby tributaries like Harris Creek and other East Coast waterways. Peak ingredients from local farmers and fishermen dictate dishes of the day, which means the super-seasonal menu changes as frequently as the tide. Bel Air, Maryland native Michael Correll, who just snagged a 2025 James Beard nomination for Best Chef Mid-Atlantic, celebrates summer with dishes like a New Jersey sea scallop crudo dressed with buttermilk, dill, and smoked trout roe, which pairs nicely with its natural wine list and well-executed cocktails. Saturday brunch service returned this summer and runs through October. 209 N. Talbot Street

Dessert

Justine’s Ice Cream Parlor, an old-timey Maryland draw since 1987, keeps scoops coming until 9 p.m. or later daily. Its cherry-red facade is hard to miss, inviting diners to indulge in a massive milkshake selection (77 in all), dozens of ice cream flavors, and sundaes. Daring dessert fans can now enter a “Titanic Sundae” challenge: devour a nearly seven-pound sundae bucket in under 15 minutes for prizes and big community cred. 106 N. Talbot Street

Go for a nightcap, come back for breakfast

Historic tavern Carpenter’s Street Saloon, lovingly called C-Street by locals, is the kind of all-day dive dreams are made of. The brick-lined bar draped in colorful flags doubles as a morning mainstay for scrapple (a Delmarva Peninsula favorite), biscuits and gravy, and home fries. C-Street seamlessly transitions by day into a late-night, no-frills hangout for plastic cups of booze, crab balls, and buzzed requests from a modern-day jukebox that plays just about every song under the sun. The 50-year-old institution even has its own weekend shuttle to get customers home safely. 113 S. Talbot Street

Other options: The Fool’s Lantern, the town’s first and only self-serve bar, features a wall of 12 drafts and 24 wines on tap alongside a menu full of charcuterie, sandwiches, and affordable crab cake feasts ($24.95). From 4 p.m. to 6 p.m. on Fridays, beers are as low as $3. 310 S. Talbot Street

A leisurely morning (and afternoon)

Check out and swing by roadside roaster Rise Up Coffee (1216 St. Michaels Road) to fuel up on single-origin beans from around the world. This tricked-out, drive-thru trailer is the location that started it all in 2005; the beloved brand has since ballooned to over 13 outposts across Maryland and Delaware. Make room in the trunk and stop by the town’s resident distillery Lyon Rum (103 E. Marengo Street) to buy bottles of its popular, small-batch spirits or saddle up to its newly expanded tasting room to sip Lyon-infused cocktails. For the ultimate collectable car buff, the Classic Motor Museum (102 E. Marengo Street) is right across the street. For a $10 admission, peruse exhibits of pre- and post-WWII automobiles, midcentury muscle cars, and vintage trucks parked inside a big barn, with a seasonal “Cars and Coffee” meetup on Saturday mornings.

After hopping in your car to drive back to reality, be sure to make one meaty pit stop to Easton’s edgy Rude Burger (4 S. Aurora Street) for excellent barbecue and bourbon in a retro pump-station setting. The tiny Maryland town of Easton is also flush with fine-dining restaurants and cafes as of late. Speaking of, the team behind Easton bagel bar Bāgery just took over St. Michaels’ historic coffee shop the Blue Crab this spring with an expanded daytime selection of quiche, burritos, and shrimp salad. Tucked inside a 19th-century Odd Fellows lodge, the yellow-toned building also carves out room for a charming Airbnb up top (102 S Fremont Street).