Annapolis is a great pick for your next night out on the town. It offers a little bit of everything: eclectic dining options, a thriving music scene, master mixologists and cozy pubs, and dozens of lodging options. And however you choose to spend your evening in Annapolis, you’ll find all your options within easy walking distance of one another. 


If your idea of a night out involves great live music, Annapolis has what you’re looking for. From nationally-recognized names to the many local musicians performing around town on a nightly basis, our small town offers a thriving music scene. One of the best things about the music venues in town is that many are housed in restaurants, making for a great night out with a bite to eat followed by some excellent music. 

Such is the case with Rams Head on Stage (located right next to Rams Head Tavern), in the heart of downtown Annapolis on West Street. Known nationally as the best music venue with under 500 seats, it is the place to go to catch a national or local act every single night. Like many other venues in town, Rams Head is a restaurant by day, serving locals and visitors their tasty dishes. However, by night, the stage is set for whatever big name star happens to be playing that night. 

Many of the area’s talented local performers frequent the town’s smaller establishments, creating an intimate, low-key setting to take in some great music. Plus, the venues are a short walk away from one another, making it easy to find a show that speaks to you. 

Master mixologists, creative cocktails, and specialized bars

Drink options are a big draw for any nightlife-lover. And Annapolis has quickly become well-known for its creative, tasty drinks served up by master mixologists. These expert bartenders change their flavors with the seasons, making sure you’re getting the freshest, best cocktails available in town. Whiskey? Tequila? Rum? No matter your taste, there’s a great bar in Annapolis serving something to your liking: rum bars, whiskey bars, tequila bars, wine bars, and those that offer a wide range of local and nationally-recognized craft beer choices. 

Annapolis Cocktail Trails

Check out local FoodieAnnapolis blogger Darin Gilliam’s "Annapolis Cocktail Trails" for a streamlined trail of bars offering a great twist on your favorite drinks. Then, park the car, hop a peddle bike, taxi, or e-cruiser and follow the trail, bouncing from place to place in search of your newest favorite drink in town. Catch highlighted cocktails from around the county on our Cocktail of the Month section, too! And, click here to browse through the many pubs, taverns, and bars in town. 


Nothing beats a great meal out on the town. Luckily, Annapolis offers a wide range to meet any taste, whether you’re looking for a fine-dining experience or want to get messy with a bushel of Maryland Blue Crabs. Restaurant goers can dine outside, on a rooftop, with a view of the Annapolis Harbor, or right next to a cozy fire, making dining here a great experience no matter the season. In addition to a variety of dining settings, you can also choose from several areas for your next meal out in Annapolis, each with unique appeal. 

Chart House

Head over to the Arts District (the first block of West Street next to Church Circle) for a bite to eat at one of the many restaurants before stopping into the many art galleries lining the street. Eastport is another great choice for great food and music. Hop over the bridge into this quaint neighborhood for some of the best views of the city. Main Street and City Dock are Annapolis staples when it comes to food, drinks, and entertainment, and a great way to experience this historic town. Maryland Avenue, one of the city’s oldest streets is home to two great restaurants, a handful of shops, and the fastest route to the United States Naval Academy. The Westfield Annapolis Mall and the Annapolis Towne Centre are two more great options for dining and entertainment.

Check out all the dining options by clicking here.

Stay the Night

After a night out on the town in Annapolis, why not stay over? With full-service hotels, B&Bs, and alternative lodging options – all a short walk away from downtown (and several in downtown) – it’s the perfect way to end a night out in Annapolis. A few of the city’s favorite restaurants are located inside these of hotels, making for a great excuse to enjoy a nightcap or midnight snack.

For a list of local accommodations, click here