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 day is easy as pie.
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, decades-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.
The heart of St. Michaels upped its laid-back luxury game last summer 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. The manicured grounds will soon grow with a pool. For now, lounge around a stone-framed fire pit at twilight to toast s’mores. 209 Talbot Street
Other options: For an elegant harborside bed-and-breakfast with antiques-filled rooms, consider the restored Hambleton Inn (202 Cherry Street). And for the ultimate overnight splurge, there’s the luxe Inn at Perry Cabin. Made famous by the movie Wedding Crashers, the postcard-perfect resort is home to special-occasion spot Stars Restaurant (308 Watkins Lane).
A surprise slice of the Italian coast lies right off the main drag. Naples natives run six-year-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) and ask its friendly female staff about their bi-annual trip to Umbria. For more European feels in the center of St. Michaels, consider recently reinvented French restaurant Bistro (403 S. Talbot Street). Originally established in 1995, 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 $6 martinis, $7 lemon vodka-infused cosmos, and pimento cheese-stuffed arancini.
The team behind Nashville’s award-winning Henrietta Red brought the strip a chic, seafood-centric American restaurant last summer 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. Tenured chef and Bel Air, Maryland native Michael Correll celebrates late summer with creative use of tomatoes, peppers, cherries, and eggplant, which all pairs nicely with its natural wine list and well-executed cocktails. 209 N. Talbot Street
Justine’s Ice Cream Parlor, an old-timey Maryland draw for over 30 years, keeps scoops coming until 10 p.m. 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. 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. 113 S. Talbot Street
A leisurely morning
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 Maryland brand has since ballooned to over 10 outposts. 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 (FYI: an under-construction tasting room with cocktails will debut in early 2023). 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, mid-century muscle cars, and vintage trucks parked inside a big barn. After hopping in your own 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.