If you look for personality, old world charm, authenticity and a lot of fun when you're out on the town, then historic downtown Annapolis is for you. Park your car and walk along our brick-lined streets en route to dozens of restaurants, pubs, and live music venues that have been serving satisfied customers for centuries.

With great food, world-class mixologists, and spectacular prices, check out happy hours in Annapolis and the Chesapeake Bay. The relaxed and casual atmosphere of this sailing hamlet makes it conducive to happy hour—any day of the week.

Pubs, Restaurants, Live Music and More

Live Msuic

In downtown Annapolis, dozens of bars and restaurants within walking distance of each other offer specials too good to pass up. You can't walk more than a block or two, or turn a corner, without finding local establishments that open their doors and their patios for not-to-be-missed happy hours in Historic Annapolis. Are you a night owl? Whether it’s a dance party, live musical performances, or a low-key night spent in a dimly whiskey bar, downtown Annapolis has it. 

The fun doesn't stop on and around Main Steet. Just over the Spa Creek Bridge, Eastport boasts its own bars, restaurant, and after dark spots where you can catch some live music on "Restaurant Row," a strip of great dining options. If it’s summertime, hop a pedicab to get over the Spa Creek bridge and into Eastport, or head to Ego Alley and climb aboard a water taxi, an ideal mode of transport in Annapolis. 

Be sure to check out our blog, Foodie Annapolis, for the latest news and updates on Annapolis cuisine, nightlife, and live music from local writers.