Events/Music
Fireside Dining
Sunday February 8th
Runs until Tuesday, March 17th, 2026
Stay warm by our fireplaces!! Good friends, hot drinks, music and games of chance.
Party like it's 1776!!
11:30 AM - 01:30 AM
Happy Hour Wed - Friday 3-7
Tuesday February 10th
Every Tuesday
Join us in the bar & Lounge for Happy hour Wed- Friday 3-7
03:00 PM - 07:00 PM
Aiden Ewald
Wednesday February 11th
06:00 PM - 09:00 PM
Lobster Night
Thursday February 12th
Thursdays every week
Lobster night Every Thursday Night $21.95
05:00 PM - 11:30 PM
Trivia
Thursday February 12th
Every Thursday
07:00 PM - 08:30 PM
Trivia every Thurs
Thursday February 12th
Every Thursday
Every Thursday @ 7pm In the Lounge
with
Extended
Happy Hour
For Trivia Teams
07:00 PM - 08:30 PM
Piano Bar Every Friday and Saturday night!
Friday February 13th
Every Friday
Piano Bar Every Friday and Saturday night! 9pm
09:00 PM - 01:00 AM
Pretty Big Deal
Friday February 13th
10:00 PM - 01:30 AM
Valentine's Day
Saturday February 14th
Join us on Valentine's Day for the perfect romantic evening!
11:00 AM - 02:00 AM
Valentine's Specials
Saturday February 14th
04:00 PM - 10:00 PM
Severn River Band
Saturday February 14th
09:00 PM - 01:30 AM
Alex Lee
Wednesday February 18th
06:00 PM - 09:00 PM
Fess up Music
Friday February 20th
10:00 PM - 01:30 AM
Mike Mchenry Tribe
Saturday February 21st
10:00 PM - 01:30 AM
National Margarita Day
Sunday February 22nd
Come celebrate National Margarita day with us on February 22nd.
11:00 AM - 11:00 PM
Michael K
Wednesday February 25th
06:00 PM - 09:00 PM
Moon Cherry
Friday February 27th
10:00 PM - 01:30 AM
All you need 02/28
Saturday February 28th
10:00 PM - 01:30 AM
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
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
Easter
Sunday April 5th
Come celebrate Easter with us!
11:00 AM - 11:00 PM
Cinco De Mayo
Tuesday May 5th
Grab your best fiesta hat and join us for Cinco de Mayo!