Events/Music
Keno & Racetrak
Monday July 7th
Runs until Saturday, November 1st, 2025
Come in and play Keno while enjoying a beverage !!
10:00 AM - 10:00 PM
Trivia Monday
Monday July 7th
Every Monday
07:00 PM - 08:30 PM
Burger & Crabcake Special All Day
Wednesday July 9th
Every Wednesday
Burger and a Pint $14.00 Crabcake and a Pint $25.00
10:00 AM - 10:00 PM
National Mojito Day
Friday July 11th
Grab a cold refreshing Mojito because it's National Mojito Day!
11:00 AM - 02:00 AM
Keno & Racetrac
Friday July 11th
Every Friday
LET'S PLAY !!
Gaming at Middleton Tavern was popular during Colonial times, when our neighbors gathered for friendly games of whist by the fireplace or wagered on upcoming horse races on West Street.
This tradition carries on in our Oyster Bar, where you can win playing Keno, betting on horses (a George Washington favorite) with RaceTrac, or testing your mettle at Monday night Trivia.
11:30 AM - 11:30 PM
WE MISS YOU MIKE CONROY
Friday July 11th
Every Friday
04:00 PM - 06:00 PM
Donald Wolcott Every Friday & Saturday!!!
Saturday July 12th
Every Saturday
Every Friday and Saturday Upstairs in the Piano Bar!!!
09:00 PM - 01:00 AM
National Scotch Day
Sunday July 27th
Come down and try our Scotch selection for National Scotch Day on July 27th!
11:00 AM - 11:00 PM
National Prosecco Day
Wednesday August 13th
Start your night with some bubbly for National Prosecco Day!
11:00 AM - 11:00 PM
National Tell a Joke Day
Saturday August 16th
...so come on down and tell us a few
11:00 AM - 02:00 AM
National Rum Day
Saturday August 16th
Join us on National Rum Day on August 16th!
11:00 AM - 02:00 AM
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
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
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
Labor Day
Monday September 1st
Come celebrate the long Labor Day weekend with us!
11:00 AM - 11:00 PM
National Cheeseburger Day
Thursday September 18th
Come grab a giant juicy cheeseburger for National Cheeseburger Day Sept 18th!
11:00 AM - 12:00 AM
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
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
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.