Curator’s statement
As a classically trained cook, travel for me is always about getting to know a destination’s culinary traditions, food scene, and the ingredients that paint the picture. I love planning trips around food experiences, and Annapolis, Maryland, is a town full of enthusiasm for the beautiful bounty of the Chesapeake Bay. Annapolis is so easy to enjoy. With its fascinating colonial backdrop and the constant buzz of sailboats on the Severn River, an oyster crawl is a delightful way to experience Charm City. Popping in and out of pubs and restaurants is effortless downtown. Parking can be tricky, and traffic can bubble up quickly in the historic downtown center, so exploring Annapolis on foot is the way to go.
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Things to do in Annapolis, Maryland
Start your oyster crawl around 5 pm, when all the restaurants are open for a busy evening service. Sailor Oyster Bar on West Street is truly special. Not only will they have plenty of local and Eastern Seaboard oysters to enjoy, but SOB also offers a Raw Bar Menu featuring little neck clams, sashimi, octopus, and more. If that’s not decadent enough, you can request a “bump” of Petrossian caviar added to your dish to make this oyster crawl unlike any other. If you’re drinking tequila tonight, Jay’s “New Fashion” is the way to go.
Make your way down West Street, through Church Circle, and then down Main Street to Annapolis Market House. This place is electric and fun. You’ll encounter character bartenders eager to serve you a Market House Lager—try one! Order a dozen Chesapeake locals and chat with your neighbor, or watch the United States Naval Academy Midshipmen stroll by in their smart “summer whites”. From here, you’ll have a great view of Ego Alley, so checking out who has the biggest yacht won’t be a problem.
After finishing your dozen at Market House, head to McGarvey’s, just a stone’s throw away. McGarvey’s is an Annapolis staple, beloved by everyone. This lively watering hole offers local oysters on the half shell for only a dollar, along with plenty of beers on tap. Their full menu is worth exploring, of course, but we’re here for the oysters—so let’s stick to the plan.
Finally, head over the Spa Creek Bridge into the neighborhood of Eastport, where you’ll get the best views of the Severn River—and boats upon boats upon boats! If you’re ready for a proper dinner, plan ahead and make a reservation at O’Leary’s Seafood. This intimate, fine-dining spot offers beautifully prepared seafood dishes and a robust wine selection. If you’d rather keep things casual, The Boatyard is delicious and lively. In addition to your oyster order, a crab cake here is never a bad idea.
Need to know
Annapolis is a lovely destination year round. May is a delight as the Blue Angels visit, the Midshipmen graduate and the weather is warm. Autumn months bring USNA football and winter is a cozy time in Annapolis. If you are traveling here by airplane, BWI is the most convenient. Have more questions? Let's connect and I will guide you along.
Travel Advisor
Christine Hargrove
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