Social Profile: 
✔️Breakfast ✔️Brunch ✔️Lunch ✔️Dinner ✔️Dine in ✔️Take out
… View more
Longtime fixture offering classic American fare including seafood & steak plus a porch & live music.
Address and Contact Information
Address: 2 Market Space, Annapolis, MD 21401
Phone: (410) 263-3323
Website: http://www.middletontavern.com/
Menu Photos
Photo Gallery
Related Web Results
Middleton Tavern – Downtown, Annapolis, MD
A wonderful traditional colonial pub and restaurant. The bar at the side has Great character and the food is fresh and nicely prepared. I especially recommend …
Middleton Tavern – Wikipedia
Middleton Tavern is a tavern in Annapolis, Maryland. It is one of the oldest continuously operating taverns in the United States. Middleton Tavern in 2009 …
Middleton Tavern | Annapolis MD – Facebook
Middleton Tavern, Annapolis. 8489 likes · 167 talking about this · 53208 were here. A sidewalk café that overlooks City Harbor, Middleton Tavern in…
Reviews
Dennise D
Great space with the fire places and bar area with TVs (for keeping up with sports). The server was great! The crab salad and crab cake sandwiches were delicious. The Bloody Mary was ‘in the middle’- tart string beans which I enjoyed but nit the person who ordered it, the spiked hot chocolate was ok- something different.
… moreSteve DeLon
Super cool Restaurant/Tavern, food and service are great, we sat outside, the view was great. We were able to see boats in the Marina. This entire section is historic and Beautiful. We also visited the Navel Academy and walked the campus. Well worth the time
… moreJessica Johnston
Came here almost 20 years ago and the crab balls were just as remembered…DELICIOUS! Excellent location, incredible food, great service. Definitely get the crab balls and try the crab dip burger. Homemade Caesar dressing was spot on, too. Hope to be back sooner than 20 years next time!
… moreDominic West
Pretty good food for the most part, had the Steam Pot which included some seafood. Personally I’m not a fan of seafood but to me it was good. I would recommend this place to anyone wanting to try some Maryland style food. I also like the history surrounding the place/building.
… moreL. H.
great location! right near the water, a great view of everything. service was great, all of the servers and hostesses were super polite and nice. we were seated very quickly, and were given menus while considering dining here. everything came out in a timely manner, fresh and hot! the menu has a good variety of options if you’re not sure what you want. the mussels are a really generous portion, and the sauce is fabulous! the wonton tuna was excellent- loved the wasabi dressing! great food, definitely will be making our way back!
… moreAlex Donithan
I gave the rating I did due to the food honestly. I got the crab dip burger and my partner got the crab cake. I also ordered the cream of crab soup (soup of the day it was) anyway my partner liked his crab cake. However I found my burger to be really bland. Even with the dip. Nothing made it that great. Our server was awesome tho. We sat at the smaller side tables outside so that was cool. Just wish there was more flavor in my burger and dip.
… moreMark Savoca
We had a great lunch at Middleton Tavern. We sat outside at this very historic tavern dating back to 1750. We had to try the raw oysters, which are local from the Chesapeake bay. They were excellent! Super fresh! My wife had the crab cake sandwich. She loves crab and said this was one of the best she has had. Fresh lump crab. I had the stacked roast beef sandwich which was also very good. Service was good, not rushed.
… moreBriana Buotte
I couldn’t even bring myself to order after visiting the restroom and coming across a 2” American roach! After seeing this little guy (bugs don’t typically bother me) I got looking around… the ceiling was covered with black dust and visible different colored molds.
I found nothing wrong with service or staff. Very friendly! But the place itself could use pest control and a good deep clean.
… moreI found nothing wrong with service or staff. Very friendly! But the place itself could use pest control and a good deep clean.
Brian Dinan
Very old school tavern, and a dying breed style of bar. This place feels lived in, and like the walls could tell some stories if they could talk. I just stopped in for a few brews, but the atmosphere was great. The bartenders were very friendly and made for a memorable experience. + for having Natty Boh on draft.
… moreHugo A.
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
… more️ 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