Maryland has some controversy over which bar claims the title of the oldest. Matt Meltzer’s Yahoo article on oldest bars credits Middleton Tavern as the oldest bar in Maryland, established in 1750, however just up the street we found a bar, Reynolds Tavern that claims they have 3 years on Middleton. If we discount Reynolds because they had converted over the years to a private residence and to a bank, than we may have to discount Middleton anyway because “The Horse You came in on Saloon” established in 1775 claims to be the oldest continuously operating bar in MD. “The horse” claims they are the only bar in Maryland that operated through prohibition. In any case, we visited both Middleton and Reynolds in Annapolis and love Maryland enough to come back someday to visit “The Horse you came in on” at Fell’s Point in Baltimore.
Middleton Tavern is located right on the end of a really cool historic area surrounding a water inlet in almost a park-like setting. The building itself is old, charming, and beautiful, but the highlight was probably the oysters Bruce enjoyed, including their famous Oyster shooters. This is a shot glass filled with an oyster and cocktail sauce to be slurped and chased with another shot glass of beer. Bruce found new love with that shot! Though the bar itself was open to a two story ceiling and was quite ornate and beautiful, it maintained its local warmth. Joining us at the bar were two regulars, one woman who makes Middleton a regular stop for lunch topped with an oyster shooter and another gentleman who happened to be from the chamber of commerce. To me, when we meet friendly locals at these bars it makes the experience more authentic and says a lot about the character of the bar.
The next stop on this double bar tour in this historic section of Annapolis was Reynolds Tavern. Reynolds Tavern was converted into a bed and breakfast tea house, but the old original kitchen in the cellar was converted into a bar. When you walk in, it feels like walking into a museum with antiques decorating the elegant dining rooms. Though we had confirmed prior to arriving that they are a tavern, I wondered if we had made a mistake since this certainly did not feel like a tavern. When we asked if they still had a bar, they lead us down stairs to a pleasantly cool cellar. The old stone walls, large kitchen fireplace, and low beamed ceilings gave the place a pleasantly quaint atmosphere. They featured local artisan beers and surprisingly a full service bar in its seemingly hidden location. The owner even joined us to talk about the buildings history which included a complete conversion in the early 1900’s to Farmer’s Bank.
Walking through this historic neighborhood of centuries old buildings, it was easy to picture what it may have been like over 200 years ago. As we passed a sign showing were the Treaty of Paris of Paris was signed, it was daunting to think of the great men including George Washington, Thomas Jefferson, Benjamin Franklin, and James Monroe, who walked these streets and even frequented Middleton Tavern, the very same place where we had just eaten lunch!
Most of these posts are written by Cheryl and edited and added to by Bruce. Learn more about us on our About us page.