Events/Music

Keno & Racetrak event photo

Keno & Racetrak

Wednesday July 9th

Runs until Saturday, November 1st, 2025

Come in and play Keno while enjoying a beverage !!

10:00 AM - 10:00 PM

2025-07-09 10:00:002025-07-09 22:00:00America/New_YorkKeno & RacetrakCome in and play Keno while enjoying a beverage !!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Burger & Crabcake Special All Day event photo

Burger & Crabcake Special All Day

Wednesday July 9th

Every Wednesday

Burger and a Pint  $14.00  Crabcake and a Pint $25.00

10:00 AM - 10:00 PM

2025-07-09 10:00:002025-07-09 22:00:00America/New_YorkBurger & Crabcake Special All DayBurger and a Pint  $14.00  Crabcake and a Pint $25.00Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com

National Mojito Day

Friday July 11th

Grab a cold refreshing Mojito because it's National Mojito Day!

11:00 AM - 02:00 AM

2025-07-11 11:00:002025-07-11 02:00:00America/New_YorkNational Mojito DayGrab a cold refreshing Mojito because it's National Mojito Day!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Keno & Racetrac event photo

Keno & Racetrac

Friday July 11th

Every Friday

LET'S PLAY !!

Gaming at Middleton Tavern  was popular during Colonial times, when our neighbors gathered for friendly games of whist by the fireplace or wagered on upcoming horse races on West Street. 

This tradition carries on in our Oyster Bar, where you can win playing Keno, betting on horses (a George Washington favorite) with RaceTrac, or testing your mettle at Monday night Trivia. 

11:30 AM - 11:30 PM

2025-07-11 11:30:002025-07-11 23:30:00America/New_YorkKeno & RacetracLET'S PLAY !!Gaming at Middleton Tavern  was popular during Colonial times, when our neighbors gathered for friendly games of whist by the fireplace or wagered on upcoming horse races on West Street. This tradition carries on in our Oyster Bar, where you can win playing Keno, betting on horses (a George Washington favorite) with RaceTrac, or testing your mettle at Monday night Trivia. Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
WE MISS YOU MIKE CONROY event photo

WE MISS YOU MIKE CONROY

Friday July 11th

Every Friday

04:00 PM - 06:00 PM

2025-07-11 16:00:002025-07-11 18:00:00America/New_YorkWE MISS YOU MIKE CONROYMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Donald Wolcott  Every Friday & Saturday!!! event photo

Donald Wolcott Every Friday & Saturday!!!

Saturday July 12th

Every Saturday

Every Friday and Saturday  Upstairs in the Piano Bar!!! 

09:00 PM - 01:00 AM

2025-07-12 21:00:002025-07-12 01:00:00America/New_YorkDonald Wolcott Every Friday & Saturday!!!Every Friday and Saturday  Upstairs in the Piano Bar!!! Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Trivia Monday event photo

Trivia Monday

Monday July 14th

Every Monday

07:00 PM - 08:30 PM

2025-07-14 19:00:002025-07-14 20:30:00America/New_YorkTrivia MondayMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com

National Scotch Day

Sunday July 27th

Come down and try our Scotch selection for National Scotch Day on July 27th!

11:00 AM - 11:00 PM

2025-07-27 11:00:002025-07-27 23:00:00America/New_YorkNational Scotch DayCome down and try our Scotch selection for National Scotch Day on July 27th!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com

National Prosecco Day

Wednesday August 13th

Start your night with some bubbly for National Prosecco Day!

11:00 AM - 11:00 PM

2025-08-13 11:00:002025-08-13 23:00:00America/New_YorkNational Prosecco DayStart your night with some bubbly for National Prosecco Day!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com

National Tell a Joke Day

Saturday August 16th

...so come on down and tell us a few

11:00 AM - 02:00 AM

2025-08-16 11:00:002025-08-16 02:00:00America/New_YorkNational Tell a Joke Day...so come on down and tell us a fewMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com

National Rum Day

Saturday August 16th

Join us on National Rum Day on August 16th!

11:00 AM - 02:00 AM

2025-08-16 11:00:002025-08-16 02:00:00America/New_YorkNational Rum DayJoin us on National Rum Day on August 16th!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com

National Pinot Noir Day

Monday August 18th

It's National Pinot Noir Day! Come enjoy a glass from our excellent selection!

11:00 AM - 11:00 PM

2025-08-18 11:00:002025-08-18 23:00:00America/New_YorkNational Pinot Noir DayIt's National Pinot Noir Day! Come enjoy a glass from our excellent selection!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com

National Whiskey Sour Day

Monday August 25th

It's National Whiskey Sour Day! Come down and let our awesome bartenders make you a great Whiskey Sour!

11:00 AM - 11:00 PM

2025-08-25 11:00:002025-08-25 23:00:00America/New_YorkNational Whiskey Sour DayIt's National Whiskey Sour Day! Come down and let our awesome bartenders make you a great Whiskey Sour!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com

National Red Wine Day

Thursday August 28th

It's National Red Wine Day! Come enjoy a glass from our excellent selection!

11:00 AM - 12:00 AM

2025-08-28 11:00:002025-08-28 00:00:00America/New_YorkNational Red Wine DayIt's National Red Wine Day! Come enjoy a glass from our excellent selection!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com

Labor Day

Monday September 1st

Come celebrate the long Labor Day weekend with us!

11:00 AM - 11:00 PM

2025-09-01 11:00:002025-09-01 23:00:00America/New_YorkLabor DayCome celebrate the long Labor Day weekend with us!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com

National Cheeseburger Day

Thursday September 18th

Come grab a giant juicy cheeseburger for National Cheeseburger Day Sept 18th!

11:00 AM - 12:00 AM

2025-09-18 11:00:002025-09-18 00:00:00America/New_YorkNational Cheeseburger DayCome grab a giant juicy cheeseburger for National Cheeseburger Day Sept 18th!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
National Drink Beer Day event photo

National Drink Beer Day

Sunday September 28th

Join us for National Drink Beer Day on Sept 28th and try one of our many craft brews!

11:00 AM - 11:00 PM

2025-09-28 11:00:002025-09-28 23:00:00America/New_YorkNational Drink Beer DayJoin us for National Drink Beer Day on Sept 28th and try one of our many craft brews!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
National Coffee Day event photo

National Coffee Day

Monday September 29th

Sit back, relax and enjoy a coffee for National Coffee Day September 29th!

11:00 AM - 11:00 PM

2025-09-29 11:00:002025-09-29 23:00:00America/New_YorkNational Coffee DaySit back, relax and enjoy a coffee for National Coffee Day September 29th!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Racetrax & Keno event photo

Racetrax & Keno

Wednesday November 12th

Wednesdays every 20 weeks

Horse racing was a popular sport in Colonial Annapolis. No one enjoyed it more than George Washington, a frequenter of Middleton Tavern. Place your bets today in the Oyster Bar with RaceTrax, from the Maryland Lottery. 

11:30 AM - 11:30 PM

2025-11-12 11:30:002025-11-12 23:30:00America/New_YorkRacetrax & KenoHorse racing was a popular sport in Colonial Annapolis. No one enjoyed it more than George Washington, a frequenter of Middleton Tavern. Place your bets today in the Oyster Bar with RaceTrax, from the Maryland Lottery. Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com