Events/Music

Trivia Monday event photo

Trivia Monday

Monday August 4th

07:00 PM - 08:30 PM

2025-08-04 19:00:002025-08-04 20:30:00America/New_YorkTrivia MondayMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Annapolis Songwriters Showcase event photo

Annapolis Songwriters Showcase

Tuesday August 5th

Every Tues in the lounge from 6-9pm  Happy Hour all Night

06:00 PM - 09:00 PM

2025-08-05 18:00:002025-08-05 21:00:00America/New_YorkAnnapolis Songwriters ShowcaseEvery Tues in the lounge from 6-9pm  Happy Hour all NightMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Lobster Night event photo

Lobster Night

Thursday August 7th

Thursdays every week

Starting Aug 14th  Lobster night Every Thursday Night  $21.95

05:00 PM - 11:30 PM

2025-08-07 17:00:002025-08-07 23:30:00America/New_YorkLobster NightStarting Aug 14th  Lobster night Every Thursday Night  $21.95Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
WE MISS YOU MIKE CONROY event photo

WE MISS YOU MIKE CONROY

Friday August 8th

Every Friday

04:00 PM - 06:00 PM

2025-08-08 16:00:002025-08-08 18:00:00America/New_YorkWE MISS YOU MIKE CONROYMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Moon Cherry event photo

Moon Cherry

Friday August 8th

09:00 PM - 01:30 AM

2025-08-08 21:00:002025-08-08 01:30:00America/New_YorkMoon CherryMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com
August Entertainment event photo

August Entertainment

Friday August 8th

Every Friday

10:00 PM - 01:30 AM

2025-08-08 22:00:002025-08-08 01:30:00America/New_YorkAugust EntertainmentMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Donald Wolcott  Every Friday & Saturday!!! event photo

Donald Wolcott Every Friday & Saturday!!!

Saturday August 9th

Every Saturday

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

09:00 PM - 01:00 AM

2025-08-09 21:00:002025-08-09 01:00:00America/New_YorkDonald Wolcott Every Friday & Saturday!!!Every Friday and Saturday  Upstairs in the Piano Bar!!! Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Severn River Band event photo

Severn River Band

Saturday August 9th

10:00 PM - 01:30 AM

2025-08-09 22:00:002025-08-09 01:30:00America/New_YorkSevern River BandMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Trivia Monday event photo

Trivia Monday

Monday August 11th

Every Monday

07:00 PM - 08:30 PM

2025-08-11 19:00:002025-08-11 20:30:00America/New_YorkTrivia MondayMiddleton 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
National Dessert Day event photo

National Dessert Day

Tuesday October 14th

Indulge in dinner and a dessert on National Dessert Day!

11:00 AM - 11:00 PM

2025-10-14 11:00:002025-10-14 23:00:00America/New_YorkNational Dessert DayIndulge in dinner and a dessert on National Dessert Day!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Halloween event photo

Halloween

Friday October 31st

Bring your best costume and join us on Halloween!

11:00 AM - 02:00 AM

2025-10-31 11:00:002025-10-31 02:00:00America/New_YorkHalloweenBring your best costume and join us on Halloween!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