Local's Guide to History & Food in Annapolis, MD
Curated By
Jessica Rausch
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USA
Maryland
Annapolis
Arts & Culture
Domestic Travel
Food & Wine
Local’s Guide
Kid-Friendly
Sightseeing
Curator’s statement
I grew up in this unique waterfront town and still visit a few times a year. I love that Annapolis feels different during each season, but my favorite time of year is October, when you're surrounded by crisp air and autumn colors during the annual boat shows. There are plenty of great restaurants, bars and boutiques in walkable downtown, many with live music nightly. Don't miss out on getting live steamed blue crabs by the dozen — locals won't mind teaching you how to open and eat!
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Insider knowledge
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Where to stay
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Day 1: City Dock & Ego Alley
Shopping and antiquing on Maryland Avenue — grab coffee from Old Fox Books, walk Main Street and State Circle, see first peacetime Capitol of the United States, which is the oldest state house in the country (1779) still in legislative use and has the oldest and largest wooden dome of its kind in the US.
Have dinner at Harry Browne's or O'Leary's Seafood for crab cakes. You won't find any filler or breadcrumbs, only jumbo lump here!
Take a post-dinner walk past all of the generic ice cream shops and grab a scoop at Annapolis Ice Cream Co. at the top of main street (they have killer pie and cobbler flavors).
Day 2: On the Water
Take a morning walk through the Naval Academy — check visitor requirements/ID here. You could spend an hour or a whole morning exploring, and be sure to visit the museum if you have an interest in naval history.
Book a sailing tour on the Schooner Woodwind you can help hoist sails or just sit back, relax and enjoy the scenic views of the Chesapeake Bay.
Head to Vin 909 in Eastport for a casual dinner. They don't take reservations so arrive early or expect a wait, but you can enjoy a (very) reasonably priced bottle of wine in the garden while you wait OR depending on the season, head to Cantler's Riverside Inn for the area's best steamed blue crabs.
Check the calendar at Rams Head On Stage, a small cabaret style music venue, for local and national acts.
Head back to main street and enjoy a bourbon cocktail at Dry 85.
Day 3: History & Gardens
Brunch at Carrol's Creek Cafe or Iron Rooster or afternoon tea followed by a pint in the beer garden at Reynold's Tavern.
Take a leisurely tour through the William Paca House & Gardens or the Hammond Harwood House.
Travel Advisor
Jessica Rausch
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