3. Middleton’s Tavern
Address: 2 Market Space, Annapolis, MD 21401, United States
Nope, don’t expect to find the Duchess of York walking through the doors any time soon. While this bar bears the same name, it’s certainly not your formal establishment. You won’t find men in tuxes and women in long dresses here, unless the entourage decided to make a quick stop on the way to the wedding. This was where the Free Masons once congregated. Nowadays, you’ll find people looking to taste the famous oyster shooters. This bar’s got energy, and once you’re there, you’ll want to bask in the fun hustle and bustle it offers.