458 Forest Beach Rd., Annapolis
Cantler’s is almost synonymous with crabs around Annapolis—hence the hour-plus wait at peak times. The dimly lit inside still feels like the original 1974 creek house—charming in its own way but not necessarily our first pick. Instead, angle for a picnic table on the deck overlooking the calm water for a mess of hot crabs plus hushpuppies, sweet corn, and plenty of light beer. Just get there early or, better yet, on a weekday.
314 Tilghman St., Oxford
Tucked away on quiet Town Creek, this nautical-chic restaurant/bar woos boaters with free docking. Small companions are welcome, too—there are special menus for both children and dogs. Adults will find lengthy cocktail and craft-beer menus—drinks are best enjoyed at the friendly dock bar—and an eclectic assortment of dishes, including Korean shrimp tacos, spicy Jamaican-style jerk-shrimp cocktail, chilled lobster rolls, and steak-frites.
304 Burns St., St. Michaels
The Crab Claw’s a classic—and a tourist mag-net—for a reason. Located on charming St. Michaels Harbor near the Chesapeake Bay Maritime Museum, the red-hued restaurant packs in visitors along outdoor picnic tables and inside a retro dining room. The food hasn’t changed drastically since the Jones family opened the place in 1965—not a bad thing when it comes to beautifully fried oysters, crispy crab balls, and steamed hard-shells.
104 W. Pier St., Oxford
As its name suggests, sunset is one of the best times to visit this restaurant—its stunning vistas of the Tred Avon River are particularly gorgeous at golden hour. You’re here for the unparalleled view first, standard crabhouse fare second—though a lively bar is a fun stop in the otherwise sleepy sailor town.
125 Mulberry St., St. Michaels
It always feels like island time here—a no-shoes-no-problem kind of dock bar inspired by the legendary Foxy’s in the British Virgin Islands. The oft-crowded watering hole overlooking St. Michaels Harbor just expanded to an adjacent property, giving patrons more room for coconut-pineapple-rum painkillers and blackened-mahi platters.
433 Kent Narrow Way N., Grasonville
On a dock overlooking Kent Island Narrows, this seafood spot—a fixture near the Bay Bridge for more than 40 years—is our favorite waterfront stop on trips to the Delaware beaches and the Eastern Shore. Multiple outdoor decks, tasty fry baskets, and Chesapeake specialties make it a destination in itself. In addition to steamed crabs, look for soft-shell clams, rockfish, and oysters from the shucking house next door.
910 Kentmorr Rd., Stevensville
You don’t need to drive to Rehoboth for a beach and an orange crush thanks to this (manmade) sandy stretch just over ten minutes from the Bay Bridge. Head to the restaurant for steamed crabs and crabcakes, a dozen styles of oysters, or crowd-pleasing pizzas before hitting the tiki bar and private beach dotted with hammocks, cornhole, and even palm trees (open Friday through Sunday, with a $5-to-$10 access fee).
1100 E. Fort Ave., Baltimore
“Waterfront” this divey Locust Point institution is not, but on the breezy rooftop you’ll catch postcard harbor views. The place is classic Charm City, with pitchers of Natty Lite and a creaky interior packed with character. We keep the well-steamed crabs—and the hushpuppies and Old Bay–sprinkled fries—coming.
6178 Tilghman Island Rd., Tilghman
Smoke and water come together beautifully at this barbecue spot on sleepy Tilghman Island. A sunny deck overlooking Knapps Narrows is a prime perch for digging into delicious spice-rubbed wings, ribs, chicken, and pulled pork. Don’t overlook seafood—the nearby Watermen’s Museum speaks to the island’s historic trade, and Marker’s crab soup is among the bay’s best.
784 Locklies Creek Rd., Topping
At roughly two and a half hours from DC, Rappahannock Oyster Co.’s scenic Virginia “tasting room” is for serious oyster day-trippers (or better yet, overnighters at the seafood company’s “Oyster Bed” Airbnb nearby). Regardless, it’s worth the drive—the surrounding water views are tough to beat, the oysters couldn’t be fresher (many are plucked from the nearby farm beds), and an outdoor grill works its magic on local seafood.
3030 Riva Rd., Riva;
1402 Colony Rd., Pasadena
If you’re tired of clawing at crowds for space at Annapolis or Baltimore crabhouses, head to these two spacious seafood destinations where you may find more boats pulling up than cars. Both the 63-year-old original in Riva and “Mike’s North” have tons of waterfront tables, tiki bars for plastic-cup crushes, heavy crabs, and tasty snacks including clams casino and hushpuppies.
700 Mill Creek Rd., Arnold
At many waterfront crabhouses, it’s a tradeoff between ho-hum fare and a great view. Not so at this typically crowded indoor/outdoor spot at Mill Creek Marina, just outside Annapolis. The setting is laid-back and lovely—especially at brunch or early evening—but chef/co-owner Bobby Jones’s deviled eggs, crabcakes, and fish tacos are even better. It’s a good sign that watermen pull up with basketloads of crabs for steaming.
305 Mulberry St., St. Michaels
St. Michaels locals lean toward this low-key restaurant in an 1830s oyster barn near St. Michaels Marina, often choosing it over the typically crowded Crab Claw across the harbor. You’ll frequently find weathered boaters at the outdoor bar and groups cracking Miles River crabs on patio picnic tables. (Part of the indoor dining room has water views, too.) Chef/owner Eric Rosen takes a from-scratch approach with the menu—nicely fried soft-shells and crispy oysters are tasty—and you can always call and reserve crabs in high sea-son. The Chesapeake fare is best washed down with a local St. Michaels Brewery beer or a Lyon Rum cocktail from the nearby distillery.
1993 Baltimore Annapolis Blvd., Annapolis
In a sea of crabhouses and dock bars, this airy New American restaurant stands out—and not just for gorgeous views of the Severn River, Annapolis, and the neighboring Naval Academy. Two waterfront decks are the best vantages in nice weather—though you can still get river panoramas inside—whether you’re brunching on crispy-oyster omelets and pulled-pork biscuits or catching the sunset over chef Nick Baker’s stellar crabcakes with fried green tomatoes.
Wylder Hotel, 21551-A Chesapeake House Dr., Tilghman
Though visiting scenic Tilghman Island is doable as a day trip, it’s worth planning a weekend at this hotel—a stylish revamp of a century-old inn, with a saltwater pool, waterfront bonfire pits, and an indoor/outdoor restaurant. Chef Jordan Lloyd, a Shore native whose résumé includes stops at Citronelle and Easton’s Bartlett Pear Inn, is behind locavore menus that range from steamed crabs to cheffy creations like rockfish imperial or steak tartare.