Events/Music

Lobster Night event photo

Lobster Night

Thursday January 8th

Thursdays every week

Starting Aug 14th  Lobster night Every Thursday Night  $21.95

05:00 PM - 11:30 PM

2026-01-08 17:00:002026-01-08 23:30:00America/New_YorkLobster NightStarting Aug 14th  Lobster night Every Thursday Night  $21.95Middleton TavernMiddleton Tavernmiddletontavern2@gmail.com
January Entertainment event photo

January Entertainment

Friday January 9th

Every Friday

Live Entertainment on both floors Friday and Saturday

Tuesday nights Singer songwriter Night

Wed Acoustic Music and Burger night

10:00 PM - 01:30 AM

2026-01-09 22:00:002026-01-09 01:30:00America/New_YorkJanuary EntertainmentLive Entertainment on both floors Friday and SaturdayTuesday nights Singer songwriter NightWed Acoustic Music and Burger nightMiddleton 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
St. Patrick's Day event photo

St. Patrick's Day

Tuesday March 17th

Grab your best green garb and join us for St. Patrick's Day!

11:00 AM - 11:00 PM

2026-03-17 11:00:002026-03-17 23:00:00America/New_YorkSt. Patrick's DayGrab your best green garb and join us for St. Patrick's Day!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