Middleton Tavern — Restaurant in Annapolis

Whenever we go to Annapolis, we always try to find this place for lunch or dinner, or just to grab a bite to eat and spend some time. We love the atmosphere, the food, and the service. I've written this review so you don't miss this lovely spot in this beautiful city.

🏛️ Middleton Tavern: A Taste of History and American Flavor in the Heart of Annapolis, MD Located in the vibrant historic district of Annapolis, Maryland, Middleton Tavern is much more than a restaurant—it’s a living monument where centuries of American history meet outstanding food and an inviting, classic atmosphere.

🍽️ Authentic American Cuisine with a Local Touch Middleton Tavern offers excellent food with generous portions and authentic flavors that reflect the rich culinary traditions of Maryland and the Northeastern U.S. One of the standout specials is the “Burger & a Pint” deal every Wednesday for just $14, paired with live music from 6 to 9 PM—a local favorite.

If you're in town on a Sunday, don't miss the brunch from 10 AM to 1 PM, perfect for wrapping up your weekend in true Annapolis style.

🎶 Live Music and a Warm Social Scene Live entertainment is one of Middleton Tavern’s hallmarks. The venue features live music every weekend, including piano performances upstairs with Donald Wolcott and local bands downstairs in the lounge. The energy kicks off at 9 PM every Friday and Saturday, with a welcoming crowd and great drinks.

Other weekly events include:

🎤 Trivia Night every Thursday at 7 PM with prizes and drink specials

🎸 Live music in the lounge every Wednesday evening

🍻 Happy Hour Wednesday to Friday, 3–7 PM in the bar and lounge

🕰️ A Rich and Storied History Founded in 1750 by Horatio Middleton, the tavern began as a portside stop for sailors traveling between Rock Hall and Annapolis. Over the centuries, it has hosted notable figures including George Washington, Thomas Jefferson, and Benjamin Franklin.

In colonial times, taverns like Middleton were vital hubs—not just for eating and sleeping, but also for conducting business, sharing news, and discussing politics. The tavern also played a key role in transportation services and shipbuilding, led by Samuel Middleton, Horatio’s son.

It also served as a meeting place for influential social groups like the Maryland Jockey Club and the Tuesday Club, a respected society of Annapolis’ most enlightened gentlemen.

🖼️ A Décor Full of Heritage The tavern’s interior is filled with artifacts and details from Maryland’s colonial past. You’ll see everything from old herb barrels and tobacco tools to oyster bar illustrations and historical prints that tell the story of Maryland’s agricultural and maritime roots.

The Oyster Bar pays homage to the fishing industry, while framed prints from the late 1800s show how oysters were harvested and served when they were the height of fashionable dining.

🇺🇸 Maryland Pride and the John Shaw Flag The restaurant also honors Maryland’s political and cultural heritage, including the legacy of John Shaw, who designed one of the first Maryland state flags flown over the State House in the 1780s. That same spirit of history and patriotism echoes throughout the tavern.

💬 Final Thoughts Middleton Tavern is not just a place to eat—it’s an experience. With its rich history, inviting American-style atmosphere, and vibrant entertainment schedule, it’s one of Annapolis’ must-visit landmarks. Whether you're a local or a traveler, you’ll enjoy excellent food, warm hospitality, and a deep connection to America’s past.

📍 Location: Downtown Annapolis, MD 📆 Closed Mondays & Tuesdays 🎶 Live music every weekend 🍔 Don't miss Burger Night Wednesdays + the...

Maybe it's the cost of living adjustment (since I was visiting from the south), but for the prices I paid for dinner, I expected much better. It wasn't even about the food (entirely). My son enjoyed his Salmon Oscar, and my Filet was decent...

For me, there were two points of failure...

1. The service (or lack thereof). My son sat twice with an empty glass. The first time, I had to ask someone else to send our server over to get it refilled. The second time, he just turned his attention to his water since we were done and ready to go. I had to ask the server to bring bread (even though the menu stated it came with the dinner). The server never offered us any dessert options at the end of the meal, but she was quick to bring a dessert plate to the people seated next to us. Was it because we were in jeans and Polos while the other folks were in shirts and ties? Did she serve them before and just happened to know them? I don't know - but what I do know is neglecting your clients is the best way to not retain them and to get a bad review.

2. The second point of failure for me was the plating of the food. It was very plain. Nothing was garnished. My filet looked out of place as the sole occupant of the plate while my potato sat on another. Even the soup and salad I and my son ordered were plated very plainly. Very disappointing for the prices. For the prices we paid, we could have gotten much better service, equally (or better) tasting food plated better, and 2 extra people in our dinner party at a chain restaurant like Longhorn Steakhouse.

I was on business travel from Charleston, SC and during the week, I had a chance to meet up with my son and have dinner with him (he lives in MD). This was a chance to have a great and special time with my son - but the overall experience was disappointing. When I am back in the area in December and he and I go out to eat in Annapolis again, we won't be stepping into...

We go to Annapolis every 4th of July. Last year was a first for this restaurant which we had a horrible experience with undercooked food, warm salad and chewy croutons, drinks incredibly overpriced to not taste good at all. Well yesterday was our second experience thinking we would give them another chance. We definitely shouldn’t have! The server (Jay) was awesome but the food was worse this time having to send back 2 dishes because they were horribly prepared. Caesar salad again was warm and the croutons chewy as you can tell they were refrigerated. Crabcake was ok but shells quickly turn you off. About 10 fries served on some of our plates with others piled on how they should be. Kids grilled cheese was horrible and cold. Burgers were cooked well done (we asked for medium well) and microwaved to reheat but the core was cold. Chicken tenders are 70% breading and were fried and then microwaved to reheat so they weren’t crunchy. The brisket was unbelievably dry and resembled roast beef sliced instead of actual brisket shredded. By the look of the bbq sauce, you can tell it was microwaved and we sent it back to be replaced with a chicken Caesar wrap that ended up being salad in a wrap with very dry and very little chicken which we also sent back. The orange crush tequila drinks were full of pulpy orange juice with a ton of seeds. I couldn’t drink it 1. Because I don’t like pulp. 2. Because who wants pulp coming through a straw with their tequila?? $14 for a cup of pulp is insane!! The manager looks super drunk with blood shot eyes last year and again this year and speaks to the staff horribly! He smoked cigarettes in the open next to our table with our small children then put the cigarettes out and placed them in his pocket! He’s sloppy and rude! The jalapeño poppers on my picante burger were also half frozen so I took them off. $178 bill for horrible food! Also, DO NOT GET THE WINGS!! You will be highly...