PhillyBite Magazine
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(Photo: Mamas Food Facebook) The Players Championship Trucks on 10
Ponte Vedra Beach - Trucks on 10, an outdoor dining location where spectators can find food items from some of the best regional food truck vendors.
Top 10: A Seafood Journey Through Annapolis, Maryland
MARYLAND STATE - Annapolis, perched on the edge of the Chesapeake Bay, is a city where the water doesn’t just shape the landscape—it flavors the plate. The Chesapeake’s bounty, particularly its blue crabs, defines Maryland cuisine, and nowhere is this more evident than Annapolis. Crab cakes reign supreme here, but the culinary adventure stretcher beyoom steamed crabs to oyster shucking and waterfront dining with a view.
We’ll dive into 10 must-try food experiences that capture the soul of Annapolis’s seafood culture. Grab a bib, a cold drink, and an appetite—let’s eat our way through the Sailing Capital.
If there’s a holy grail of crab cakes in Annapolis, Boatyard Bar & Grill might hold it. Tucked in the Eastport neighborhood, this nautical hangout lives by a “no filler, all crab” creed. Their crab cakes are a masterpiece of jumbo lump crab meat, kissed with just enough seasoning to let the sweet, tender crab shine. Served with a subtle house-made tartar sauce, they’re the kind of dish that makes you pause mid-bite to appreciate the Chesapeake’s magic. The vibe is pure Annapolis—laid-back, maritime, and welcoming, with boaters fresh from the docks swapping stories over beers. Pro tip: Pair your crab cake with a view of the Mari,na, and thank me later.
Since 1974, Cantler’s Riverside Inn has been the waterfront king of crab feasts. A short drive from downtown, this rustic gem sits on Mill Creek, where the outdoor deck practically begs you to roll up your sleeves and get cracking. Order a dozen steamed Maryland blue crabs, dusted with Old Bay, and dive into the messy, glorious ritual of picking meat frothe m shell. Want a crab cake instead? They’ve got those too—a perfect blend of lump and smaller crab pieces, served with coleslaw. It’s a locals’ favorite for a reason: the seafood’s fresh, the setting’s unbeatable, and the experience feels like a Chesapeake rite of passage.
Chick & Ruth’s Delly is an Annapolis institution serving crab cakes that could star in a foodie’s dream in the heart of downtown. These colossal beauties are all about jumbo lump crab meat, minimally bound and bursting with flavor. The no-frills, family-run deli has been a fixture since the 1960s, earning nods from locals and luminaries alike—rumor has it even governors have sung their praises. Eat in to soak up the retro charm (and join the daily Pledge of Allegiance at 8:30 a.m.), or order to-go if you can’t resist sharing the love. Either way, it’s a taste oAnnapolis'sis history.
Don’t judge a crab cake by its cover—Dock Street Bar & Grill might look like a dive, but it’s a culinary contender. Perched on Ego Alley, where boats strut their stuff, this unpretentious spot surprises with crab cakewithck big lumps and bold taste. Local polls, like Naptown Scoop’s, consistently rank them near the top, and it’s easy to see why: they’re hearty, flavorful, and served with a side of waterfront vibes. Dock your boat, grab a stool, and savor hidden provinces. Annapolis’s best bites don’t always have a fancy facade.
Location: 410 Severn Ave, Annapolis, MD 21403
For a crab cake with a side of sophistication, Carrol’s Creek Café delivers. This waterfront spot overlooks the Annapolis skyline, pairing stunning views with a well-balanced crab cake from fresh, local crab meat. The focus here is on simplicity—minimal filler, maximum flavor—served in an upscale yet approachable setting. It’s perfect for a special night out or a leisurely lunch when you want to linger over the scenery. Bonus: the outdoor patio in milder months (yes, even February can surprise you with a warm day) makes every bite feel like a celebration.
Oysters are Chesapeake royalty, and The Choptank knows how to treat them right. This modern seafood joint offers a rotating selection of local oysters, shucked fresh and served raw, roasted, or fried. Pair them with a craft beer or a crisp white wine, and settle into the sleek, airy space that nods to Annapolis’s maritime roots. The vibe’s a bit trendier than the old-school crab shacks, but the commitment to quality is pure Maryland. Time your visit for happy hour if you’re craving a deal—those oyster specials are hard to beat.
A stone’s throw from City Dock, Middleton Tavern has been feeding Annapolis since 1750, and their crab dip is a modern classic. Creamy, cheesy, and loaded with crab meat, it’s served warm with bread or crackers—perfect for sharing (or not). The historic setting, with its low ceilings and colonial charm, adds a layer of timelessness to the experience. Sit by the fireplace in winter or snag a spot on the patio overlooking the water in warmer weather. It’s comfort food with a Chesapeake twit, and a must for any foodie’s itinerary.
McGarvey’s is a downtown staple where the crab soup steals the show. Choose between the cream of crab—rich, velvety, and studded with lump meat—or the Maryland crab, a spiced tomato-based broth that’s pure comfort in a bowl. Both showcase the bay’s finest and are hearty enough to stand alone or pair with a sandwich. The saloon’s lively atmosphere, complete with a raw bar and a storied past, makes it an excellent stop for a quick lunch or a long evening of people-watching along Market Space.
When soft-shell crab season hits (typically spring through early fall), O’Learys is the place to be. These delicate, edible crabs are lightly battered and fried, offering a crunchy exterior and a succulent bite that’s pure Chesapeake bliss. The restaurant’s cozy, upscale vibe in Eastport feels like a local secret, though its reputation draws seafood lovers from afar. If you’re visiting outside peak season, their year-round crab dishes—liCrab Imperialial—keep the spirit alive. It’s a treat worth timing your trip for.
Round out your Chesapeake culinary tour at Pusser’s, where the seafood meets a tropical twist. Their crab cakes are solid, but the real draw is the combo of fresh fish tacos or crab-stuffed shrimp with a Painkiller cocktail—a rum-soaked nod to their Caribbean flair. Perched at the Annapolis Marriott Waterfront, the outdoor deck overlooks the harbor, making it a prime spot to watch boats glide by. It’s a laid-back finale to a chapter of eating, blending local flavors with a dash of island escape.
These 10 experiences are just the start of Annapolis’s edible allure. The city’s crab cakes—whether purist masterpieces or dive-bar surprises—set the standard, but the oysters, soups, and soft shells prove there’s more to taste in this Chesapeake gem. Each spot offers a slice of Annapolis life: the boaters at Boatyard, the history at Middleton, and the hustle of downtown at McGarvey’s. Hungry for more? The next chapter takes you onto the water—because in Annapolis, the bay isn’t just a backdrop; it’s the beating heart of every adventure.
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Best Hot Dog Spots in The State of South Carolina?
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