Events/Music

Lobster Night event photo

Lobster Night

Thursday December 4th

Thursdays every week

Starting Aug 14th  Lobster night Every Thursday Night  $21.95

05:00 PM - 11:30 PM

2025-12-04 17:00:002025-12-04 23:30:00America/New_YorkLobster NightStarting Aug 14th  Lobster night Every Thursday Night  $21.95Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Trivia Monday event photo

Trivia Monday

Monday December 8th

Every Monday

07:00 PM - 08:30 PM

2025-12-08 19:00:002025-12-08 20:30:00America/New_YorkTrivia MondayMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Christmas Sing Along event photo

Christmas Sing Along

Thursday December 11th

Come and sing  along with Christmas songs  during Midnight Madness

06:00 PM - 09:00 PM

2025-12-11 18:00:002025-12-11 21:00:00America/New_YorkChristmas Sing AlongCome and sing  along with Christmas songs  during Midnight MadnessMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Ugly Sweater Party With All  You Need Band event photo

Ugly Sweater Party With All You Need Band

Saturday December 13th

10:00 PM - 01:30 AM

2025-12-13 22:00:002025-12-13 01:30:00America/New_YorkUgly Sweater Party With All You Need BandMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Christmas Sing Along event photo

Christmas Sing Along

Thursday December 18th

Come and sing  along with Christmas songs  during Midnight Madness

06:00 PM - 09:00 PM

2025-12-18 18:00:002025-12-18 21:00:00America/New_YorkChristmas Sing AlongCome and sing  along with Christmas songs  during Midnight MadnessMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Ghost Story Dinner  Get your tickets now! event photo

Ghost Story Dinner Get your tickets now!

Tuesday December 23rd

Dinner and Stories    

07:00 PM - 09:00 PM

2025-12-23 19:00:002025-12-23 21:00:00America/New_YorkGhost Story Dinner Get your tickets now!Dinner and Stories    Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Christmas  Closed event photo

Christmas Closed

Thursday December 25th

Happy Holidays to all of our fans! We will be closed so our employees can enjoy the holiday!

11:00 AM -

2025-12-25 11:00:002025-12-25 America/New_YorkChristmas ClosedHappy Holidays to all of our fans! We will be closed so our employees can enjoy the holiday!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
New Year's Eve event photo

New Year's Eve

Wednesday December 31st

Celebrate the New Year with us and join us on New Year's Eve!

Rickshaw Lizard starts @ 10pm in the Lounge.

Donald upstairs on the Piano starting at 9pm

11:30 AM - 01:30 AM

2025-12-31 11:30:002025-12-31 01:30:00America/New_YorkNew Year's EveCelebrate the New Year with us and join us on New Year's Eve!Rickshaw Lizard starts @ 10pm in the Lounge.Donald upstairs on the Piano starting at 9pmMiddleton TavernMiddleton Tavernmiddletontavern2@gmail.com

Valentine's Day

Saturday February 14th

Join us on Valentine's Day for the perfect romantic evening!

11:00 AM - 02:00 AM

2026-02-14 11:00:002026-02-14 02:00:00America/New_YorkValentine's DayJoin us on Valentine's Day for the perfect romantic evening!Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com

National Margarita Day

Sunday February 22nd

Come celebrate National Margarita day with us on February 22nd.

11:00 AM - 11:00 PM

2026-02-22 11:00:002026-02-22 23:00:00America/New_YorkNational Margarita DayCome celebrate National Margarita day with us on February 22nd.Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
Racetrax & Keno event photo

Racetrax & Keno

Wednesday April 1st

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

2026-04-01 11:30:002026-04-01 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