Before America was even a country, this legendary tavern was already serving food, pouring drinks, and welcoming travelers through its doors.
276 years later, people still pull up a chair inside the same historic building for classic Maryland comfort food.
Between then and now, the tavern has hosted colonial lawmakers, Revolutionary War figures, sailors, tourists, and generations of Annapolis locals.
It is lively, packed with seafood, and still buzzing with energy nearly three centuries after opening.
And once you see what is inside, you will understand why people keep coming back.
Where Is It?
Middleton Tavern is located at 2 Market Space in downtown Annapolis, Maryland, right along the historic City Dock.
You’ll find it within walking distance of Ego Alley, the U.S. Naval Academy, and waterfront streets lined with sailboats and seafood restaurants.
It’s also about a 40-minute drive from Baltimore, around 45 minutes from Washington, D.C., and roughly 2 hours from Philadelphia.
About
Middleton Tavern is one of the most famous waterfront restaurants in Annapolis, and the second you walk inside, you can tell this place has stories to tell.
It feels cozy and lively, with two levels and a main dining room filled with old-fashioned tavern décor, wooden tables, and a fireplace.
The walls are decorated with nautical artwork, framed photographs, and memorabilia inspired by Annapolis and Chesapeake Bay culture.
You’ll also spot a long wooden bar surrounded by sports banners, hanging flags, TVs, and lively crowds during game days and busy weekends.
The highlight here though is the outdoor seating area, where tables sit just feet from the narrow waterway.
It’s an easy spot to settle in, enjoy the fresh air, and linger over good food for hours.
Speaking of the food, the menu leans heavily into classic Maryland favorites.
You’ll find crab cakes loaded with jumbo lump crab meat, oysters from the Chesapeake Bay, crab soup, and shrimp salad sandwiches.
The tavern is also well known for its raw bar specials, including steamed shrimp, clams, and mussels.
If seafood isn’t your thing, there are Black Angus burgers, roast beef sandwiches, steaks, and desserts like crème brûlée, chocolate cake, and cheesecake.
Whether you come for the food, the history, or the lively atmosphere, Middleton Tavern is easily a must-visit in the city.
History
Now for the fun part, because Middleton Tavern has been around longer than the United States itself.
When Horatio Middleton ran a ferry across the Chesapeake Bay in 1750, colonial law required operators to provide lodging for travelers.
As a result, Middleton Tavern opened as an inn and tavern that welcomed sailors, merchants, and visitors passing through Annapolis.
It eventually grew into one of the city’s major social gathering spots, hosting clubs, meetings, and well-known local organizations of the time.
What makes it even more interesting is its connection to America’s Founding Fathers.
George Washington, Thomas Jefferson, and Benjamin Franklin all visited the tavern during its early years.
That little detail adds to the experience, because your meal could be served in the same rooms where early American leaders once talked politics over drinks.
After the Revolution, the tavern continued to serve Annapolis as the city grew, changed, and shifted from a colonial port town to Maryland’s capital city.
And even after years of renovations and repairs, the building holds onto its old tavern charm that people still love today.
That long history makes Middleton Tavern one of the oldest continuously operating taverns in the United States.
After 276 years, it still does what it was originally built to do by feeding people, bringing them together, and keeping the conversation going.
Know Before You Go
Hours
Middleton Tavern is open daily, with slightly different hours depending on the day.
- Monday to Thursday: 11:30 a.m. to 10 p.m.
- Friday to Saturday: 11:30 a.m. to 1:30 a.m.
- Sunday: 10 a.m. to 10 p.m.
Best Time to Visit
If you want the best waterfront experience, try visiting between late spring and early fall.
That’s when Annapolis really comes alive with outdoor dining, sailboats filling nearby Ego Alley, and warm weather that is perfect for walking around after a meal.
For a quieter experience, weekday afternoons offer the same gorgeous views and historic atmosphere without the long wait for a table on a weekend.
Parking
Parking downtown can get crowded fast, especially on weekends, so arriving early gives you a much better chance of finding street parking.
One of the nearest backup options for parking is the Hillman Garage at 150 Gorman Street, roughly five minutes away on foot.
Things to Do Nearby
Once you finish your meal, you can easily spend the rest of the afternoon exploring nearby attractions and historic landmarks around downtown Annapolis.
You can walk about 10 minutes to the U.S. Naval Academy Museum, which features exhibits, guided tours, and displays exploring Navy history.
There’s also the Maryland State House, located about a 6-minute walk away and known as the oldest state capitol still in continuous legislative use since 1772.
If you want to keep wandering afterward, head to Main Street for boutiques, bookstores, coffee shops, and ice cream spots.
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