Annapolis serves up history, one drink at a time.
Annapolis, one of America's best-preserved colonial towns, sits right on the Chesapeake Bay. Painted clapboard houses line its brick pavements, and boats bob gently in the harbour below. Its history runs right through its pubs and taverns too, several of which have been serving drinks for well over a century, some for well over two. Here's where to start.
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Middleton Tavern
Founded in 1750, Middleton Tavern is one of the oldest continuously operating taverns in America, which makes it about as good a place as any to begin. Settle in on the ground floor for oysters and a cocktail by the fireplace, or head upstairs to the piano bar for something livelier, with a good range of draught beers and signature cocktails either way.
Historic 1747 Pub at Reynolds Tavern
As its name suggests, this one has been around rather longer than most. The pub occupies the original 1747 kitchen of local merchant William Reynolds' tavern, and it still looks the part: stone and brick walls, low ceilings, walk-in fireplaces and the original staircase all remain. Settle in with a plate of proper pub fare, think bangers and mash or a bowl of cream of crab soup, and one of the pub's own Colonial Punches.
Drummer's Lot
Tucked away, practically hidden, inside the historic Maryland Inn, Drummer's Lot has been open since 1784. Beyond its threshold is an old-time charm, a warm blend of family and elegance. Order a classic bourbon Old Fashioned and enjoy your drink much the same way kings and heads of state might once have taken theirs in colonial times.
Rams Head Tavern
Once known as the Crown and Dial Tavern in the 18th century, Rams Head Tavern is a lively, easy-going stop on any crawl. It's a proper beer-lover's pub: the original home of Fordham craft beers, with a huge selection besides, and a characterful downstairs bar and back garden that only add to the appeal.
The Federal House Bar and Grille
Founded in 1830, The Federal House pairs its history with genuine energy: live music plays here every night of the week. In the winter you can warm up by the outdoor fire tables, and the Champagne Super-Nova, a house favourite, is a fine way to kick off the evening. Don't leave without trying the cream of crab soup, a real local point of pride.
Galway Bay Irish Restaurant
Housed in a building dating from 1897 to 1903, once home to the historic Little Campus Inn, Galway Bay brings a proper Irish welcome to the heart of colonial Annapolis. There's live traditional Irish music through the week and an award-winning whiskey bar stocked with rare Irish drams, reason enough to settle in for the evening.
Harold Black
For something a little different, duck below Acqua al 2 at the corner of Church Circle and Main Street, where you'll find Harold Black, a speakeasy founded in 2022. The building above was raised in the early twentieth century, on the remnants of three 19th-century structures, for the Annapolis Banking & Trust Company. Below, it's all low light, carefully made cocktails and an Italian menu, a proper hidden gem.
The Parley Room
On the ground floor of the historic Capital Hotel on State Circle sits the Parley Room, set inside a building some 250 to 300 years old but fully renovated with a distinctly 1920s feel. Think inventive small plates, build-your-own charcuterie boards and bespoke cocktails. It's one of the newer additions to the Annapolis scene, having opened in November 2022, but well worth seeking out.
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Whichever route you take, and whichever pubs you stop at along the way, an Annapolis tavern trail is one of the most memorable, and most delicious, ways to get under the skin of a genuinely historic American city. Great company, great drinks, and plenty of stories behind every bar.
Posted by: Visit Annapolis & Anne Arundel County
Posted on: 11/08/2026