Annapolis hums at night. No matter what season. People are constantly adventuring about, hopping from pub to pub into the wee hours. You can stroll into just about any establishment and strike up a conversation with the person next to you and become friends for 10 minutes or an hour.
The nightlife is casual but, with the Naval Academy Middies walking about in their dress-white uniforms, it’s a slightly dressier casual. In the summer, woman tend to wear sundresses or boating-wear while guys sport dress-shorts of assorted colors. Jeans rule in the winter, but some places are dressier and those are noted. It’s not unusual to see people walk-by in formal evening wear year-round on their way to events at the many historic buildings.
Annapolis is a park-and-walk kind of place. Parking spots fill up quickly on weekend nights. Once you park, if you want to venture farther than you want to walk, flag down a trolly, cab, pedicab or the electric cart. (See the Getting Around section.)
Downtown Annapolis near City Dock
The harbor-front area contains a variety of restaurants with sidewalk seating during warmer weather. At night on weekends, many take the tables away as bands or DJs set up. Bars tend to fill up by 10pm when the bands start and go until 1am. Some place stay open until 2am. Here’s what you’ll find:
Using City Dock as a starting point — across the water of Ego Alley, and set away from other bars, is Pussers Caribbean Grille (80 Compromise Street) in the Annapolis Waterfront Marriott. It’s styled like a British pub and clears out for a DJ at night. It’s a big place and can get crowded with 20-30 year olds. It’s also a little dressier with a dance club feel. The restaurant seating area goes to the edge of the water and bouncers standby on summer nights to keep people from falling in among the boats.
About a block away, across Spa Creek, is Blackwall Hitch (400 Sixth Street). It’s in the renovated former Rockfish bar. Blackwall Hitch has a combination of live music and DJ. There’s a rooftop bar overlooking Spa Creek from a distance. You can see the masts of the sailboats and a bit of water. The rooftop closes at 10pm. Inside, they clear the tables away after 10pm and pump up the music. It’s a mixed crowd on the dressier side.
Back at City Dock are Armadillo’s (132 Dock Street) & Dock Street (136 Dock Street), two small dive bars next to each other in historic buildings. Dock Street has either a DJ or band with a cover charge. Armadillo’s serves food until 11pm, but most of the tables are moved at night to squeeze in a rock band and dancing. It also has a cover charge, but 2-for-1 drinks until 10pm.
(Note: “dive bar” is a description for those who enjoy casual bars that have been around many years without much change.)
The next block up has two historic taverns. Middleton Tavern (2 Market Space) was established in 1750. On Fridays and Saturdays, the tables are cleared away in the ground-floor bar for bands that range from oldies rock, to blues and reggae. There’s no cover charge. The crowd tends to be older, 40s and up, and tends to erupt in hand-dancing or singing along with the band.
On the second floor is a laid-back piano bar, across from a dining room. Get there early to perch on one of the stools that ring the piano. It’s a popular place for people of all ages. Sure, you’ll hear plenty of Billy Joel, but you’ll also get current ‘Top 40s’ tunes.
And next to Middleton’s is McGarvey’a Saloon & Oyster Bar (8 Market Space); the only Annapolis restaurant with a tree growing in the middle of the dining room. Food is served until 10pm, then tables are pulled aside. There are two bars. The front bar is narrow with a tin ceiling; naval aviator helmets line the top of the dark wood bar. That’s where you’ll find plenty of TVs for watching Ravens football.
Go through side door in the back, and you find the oyster bar area, an open high-ceiling room with brick and wood-paneled walls and antique-tiled floor. At night, the oyster bar closes and the craft-beer bar takes the lead. Dancing can break out in either bar, but there’s no “dance floor.” The age skews middle range, 30s-50s.
Turning the corner, on your way to main street, is Federal House (22 Market Space), established in 1830. They have live music during the week and DJs on the weekend. They card everyone, even old folk, but the bouncer makes it seem flattering. The main room is an atrium with stairs to a loft dining area. The atrium turns into a disco at night that has the feel of a big city warehouse disco. The DJs feature the latest dance hits, drawing a younger crowd, 20s-30s. The bar features micro brews on tap.
Heading up the hill on Main Street are a variety of bars. We’ll begin with O’Brien’s (113 Main Street), an Irish pub. At night, O’Brien’s breaks-off into an urban dance club. Doors are pulled aside in the back room to reveal a DJ stand and a stripper pole. The pole is not connected on top, so words of advice — no flipping upside-down on the pole.
O’Brien’s has two bars. The front bar is square and surrounded by TVs for sports watching. Tables are removed from the back bar area. The room is big with a small bar to create a wide open dance floor. The DJ features an urban mix of techno and dancehall. “Shot Girls” walk around selling jello shots in fake syringes strapped crisscrossed like ammo belts. The crowd is younger, 20s-30s, and women are a little more dressed up than other dance places in Annapolis. There is a cover charge, for guys only though.
Then there’s Acme Bar & Grill (163 Main Street). It can be easily missed, as it’s a small place tucked between Main Street shops. It’s a dive sports bar with 10 flat screen TVs all the way around the bar, and snow boards hanging on the walls (there’s no place to snowboard anywhere near Annapolis, it’s just a cool look). Beer is served in pitchers. At night, a DJ takes over the long, narrow bar. It’s a young place, 20s-30s.
Castlebay Irish Pub (193 Main Street) is about half-way up Main Street. It’s decorated in traditional Irish pub-style dark, Honduran mahogany and stained glass, and features imported and domestic ales. Police and firefighter patches from across the U.S. cover the bar. Two dart boards can be found in the back. They’ll have acoustic music and small bands Thursday-Saturday nights and karaoke on Sundays. Tuesday is traditional music night.
If you want to experience intimate, historic colonial pubs, the next two are the best examples:
At the top of Main Street, is the historic Maryland Inn (58 State Circle) established in 1784. Continental Congress delegates stayed there when Annapolis was the temporary U.S. capitol under George Washington. The bar is in the basement. Walk in the side door, down the hall and you’ll find the Drummer’s Lot Pub, a small, intimate bar. It’s small enough that the conversation can cross the length of the bar and new arrivals often join right in. It specializes in fine wines and cocktails. There is no loud music. It’s a dressier place and the crowd trends older, 40s & up. It has a single flat screen TV and the sound is turned up for Ravens games.
The next block up, across from St. Anne’s Parish church, check out Reynolds Tavern’s 1747 Pub (7 Church Circle). You get to the pub by going down stairs at outside of the historic colonial home. The pub is in the original kitchen and ‘Hat Shop’ of William Reynolds. It has stone and brick walls, walk-in fireplace, low ceilings, brick floors, and the original stairwell from the 1737 construction. Over the doorway is “a little rebellion now and again is a good thing,” said by Thomas Jefferson to James Madison, Paris, January 30, 1787. The pub features craft beer and has live music on weekends. In nice weather (year round), they open the patio in back of the tavern.
And off the beaten path — Galway Bay (63 Maryland Avenue), an Irish pub off the state capitol circle. It’s a relaxed, casual place with no TV and proud of it. They hold the “Perfect Pint” award from Guinness (for pouring the beer the proper Irish way), and also serve their own brand of locally brewed lager and ale. It’s a place you go for a quiet drink and conversation and is a popular spot for St. John’s & Naval Academy students and professors, also drawing state capitol clientele and drinkers of all ages.
If downtown Annapolis hums, West Street swings. Most of the larger bars in this uptown area have live bands on the weekends and frequently on weekday nights.
The nightlife area lines West Street from Church Circle and to West Gate Circle. It’s a 10-15 minute walk — about a half-mile — uphill from the waterfront, but it’s not a steep hill. Trolleys, bicycle rickshaws and a electric car (large golf cart) continually circle downtown and West Street for those who’d rather ride.
Starting at Church Circle (at the top of the hill), is Rams Head (33 West Street) an English pub often with a tour bus parked in front because there are two parts to Rams Head: On Stage, which features live music nightly — often major acts stopping in Annapolis between gigs in major cities — and the Tavern, which may have a small combo in the back garden or in the basement pub.
The building has been a tavern of various forms since 1700s and current owners have maintained the original feel. On Stage is a open room filled with tables to encourage people to order food and drinks before the act begins.
The Tavern is a combination of several bar and restaurant areas. It’s slightly more upscale than other West Street bars and has an older crowd. On the left as you walk in are large beer vats. Before it was Rams Head, the building was home to Fordham Brewing Company, one of the early craft breweries in Maryland. They’re now Fordham and Dominion Brewing Company based in Delaware. Fordham had to remove the roof to install the vats and left them behind when they moved.
In the front of Rams Head is a small well-polished English bar with brass beer taps. The beer garden is in the back with an ivy-covered trellis providing shade. The casual pub is in the basement with bar seating for ten and table seating for maybe 30 if everyone squeezes and gets to know each other. Pewter mugs hang from the low ceiling.
Next door is Stan and Joe’s Saloon (37 West Street), a beat up (well-loved) Irish sports bar. It’s the kind of place where the local sports teams go for a draft and darts after the game. In other words, very casual. It’s a long, narrow bar with a pressed-tin ceiling and lined with tables and flat screen TVs. It widens out just enough for a dance floor every night after 10pm. In the back, is a small, colorful outdoor beer garden with picnic tables and beers served in buckets. A crush machine stands at the ready. The cliental trends younger, but there’s a good mix of older folk who prefer casual.
49 West (49 West Street) is deceiving. It’s a coffee house/wine bar and looks like a typical indie coffee house with mismatched chairs and cups. But it has a full bar, and if you walk all the way to the back, there’s a jazz club. It’s a dumpy room with red velvet curtains barely hanging on over the windows, but nearly every night people squeeze around small tables to listen to quality jazz and blues. It has that smokey jazz joint feel without the smoke.
Tsunami (51 West Street) features sushi, but at night turns into a hipsters’ hang-out. It’s a place to sip a cocktail and talk; there’s no band or DJ. The restaurant bills itself as “dark and sexy — perfect for a date night or a night out with friends.”
About midway of West Street is Metropolitan Kitchen and Lounge (169 West Street), in a modern building where the edgier types hang out. That’s where you’re most likely to find those who dress in big city variations of black and bling. The first floor is given over to the restaurant specializing in farm-to-table local food. The second floor is the Met Lounge, a modern grunge bar featuring independent and alternative music, as well as DJs. The Rooftop, on the third floor, an elegant outdoor bar with a mix of modern couches and tables. Long drapes flutter in in the breeze. A California-style glass wall lines the rooftop, opening up the view of West Street. It can be very romantic.
The last of West Street’s big bars is Fado Irish Pub (1 Park Place) at West Gate Circle, the Annapolis version of a popular Washington, DC pub. It’s in a relatively new building (for Annapolis) but the bar looks old. It was designed and made in Ireland then shipped to Annapolis for installation. You’ll find soccer or rugby on the big flat screen TVs rather than the standard background ESPN. They’ll occasionally have a singer with a guitar playing Irish songs. Patrons represent all age range.
There are a number of fine smaller places in between the big bars, including a wine bar, as well as Thai, Mexican and Italian restaurants. Even a Dunkin Donuts that’s open late.