Events/Music
Trivia Monday
Monday August 4th
Every Monday
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
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
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
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
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
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!!!
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
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
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
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
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
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
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
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