Hugo A.
Google
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 upstairs Piano Bar