NOTE: This page and products mentioned are intended only for those of legal drinking age 
Main Street in Annapolis at night
Main Street in Annapolis

Annapolis hums at night. No matter what season. People are constantly adventuring about into the wee hours. You can stroll into just about any establishment and strike up a conversation with the person next to you, becoming friends for 10 minutes or an hour.

The Annapolis 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, women 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 wearing 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 trolley, cab, pedicab, or electric cart. (See the Getting Around section.)

The historic area offers a different type of nightlife experience depending on which section you’re visiting.

City Dock at Night

City Dock, also called Ego Alley, is the Annapolis waterfront area.  Using the top of City Dock as a starting point where it’s closest to downtown, you’ll notice Market House first. It’s an indoor market with several food vendors, a great place for cheap eats and a beer while sitting outside at the metal tables or across the street at the steps facing the water

Behind Market House are rows of historic buildings with lively restaurants connected in the shape of an “L.” Many have live music on the weekends.

The Market Space Party

Federal House (22 Market Space) was established in 1830. 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 microbrews on tap.

Iron Rooster (12 Market Space) is mainly a higher-end comfort food restaurant, but it has a small, quiet bar that’s nice for conversations.

The Party on Pinkney Street

Middleton's Tavern in Annapolis, MD
Middleton’s Tavern. McGarvey’s Saloon is next door on the left.

This short end of the “L” has two historic Colonial 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 will 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’s 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.

Go through the side door in the back, and you find the oyster bar area, an open high-ceiling room with brick and wood-paneled walls, and an 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.

The Party on Dock Street

Dock Street parallels City Dock on the parking lot side. This is where you find two small but beloved dive bars in a row of historic brick buildings — Armadillo’s  (132 Dock Street) & Dock Street (136 Dock Street). Dock Street (the bar) 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. Both overflow with the college crowd on warm summer nights.

NOTE: “Dive bar” is a description for those who enjoy casual bars that have been around many years without much change.

The Party on Compromise Street

Compromise Street is across the water, opposite Dock Street. That’s where you’ll find Pussers Caribbean Grille (80 Compromise Street). 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- to 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.

Nightlife on Annapolis’ Main Street

A variety of restaurants along Main Street now squeeze in sidewalk seating during warmer weather. At night on weekends, many take the tables away as bands or DJs set up inside. Bars tend to fill up by 10pm when the bands start and go until 1am.

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 backroom to reveal a DJ stand.

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. The crowd is younger, 20s-30s, and women are a little more dressed up than in other dance places in Annapolis.

A few buildings up the street is Vitola 121 (121 Main Street), a cigar bar with a bit of a speakeasy feel. This is a private club with wood-paneled rooms containing leather chairs, however, they allow visitors for a $30 fee, which is applied toward cigar purchases. No liquor license yet, but you can bring your bourbon. Amazingly the small entry room doesn’t smell like cigars, due to a state-of-the-art ventilation system.

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 around the bar, and snowboards 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 halfway 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.

At the top of Main Street — 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.

Church Circle

There’s not much happening around the Church Circle, but we have to mention Reynolds Tavern’s 1747 Pub (7 Church Circle). You get to the pub by going downstairs outside of the historic colonial home. It’s a bit like a Colonial speakeasy.

The pub is in the original kitchen and ‘Hat Shop’ of William Reynolds.  It has stone and brick walls, a 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 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 the back of the tavern.

State Circle

State Circle is also a quiet area at night with one place that’s worth a mention, Harry Browne’s Restaurant (66 State Circle) across the street from the Maryland State House. It’s a steak house with white linen tablecloths, but the action is upstairs. That’s where the bar is located. This is where you go for $$$ martinis and wine. The bar stays open later than other places if enough patrons are there having a good time.

Maryland Avenue Nightlife

And off the beaten path — Galway Bay (63 Maryland Avenue), an Irish pub off the state capital 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 brand of locally brewed lager and ale. Galway also has a huge selection of Irish and Scotch whiskey and offers flights. It’s a place you go for a quiet drink and conversation and is a popular spot for St. John’s & Naval Academy students as well as professors. They have traditional Irish music every Sunday afternoon from 4pm-8pm.

West Street Nightlife

West Street Annapolis
West Street is also known as Annapolis’ Arts and Entertainment District.

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.

West Street is the “Arts and Entertainment District” in Annapolis and fills with hipsters. The nightlife area lines West Street from Church Circle to West Gate Circle. It’s a 10-15 minute walk — about a half-mile — uphill from the waterfront. Trolleys, bicycle rickshaws, and an 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 the basement pub.

The Tavern is slightly more upscale than other West Street bars and has an older crowd. 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 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 down 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, is an elegant outdoor bar with a mix of modern couches and tables. Long drapes flutter in the breeze. A California-style glass wall lines the rooftop, opening up the view of West Street. It can be very romantic.

There are 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.

Eastport Nightlife

Eastport, on the other side of Spa Creek from Downtown Annapolis, is a separate world. Eastport is a mix of younger and older, and nobody cares because they share a lifestyle — boating. The nightlife is split between high-end restaurants with quiet bars and rocking boater-hangouts.

The exception is Blackwall Hitch (400 Sixth Street), which combines both. 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.

Going down Severn Avenue, you’ll come across the Boatyard Bar & Grill (400 Fourth Street). It hosts fishermen and boater nighttime events throughout the year and will clear out a section of the bar for a live band and causal dancing. Mostly, it’s just a popular evening hangout.

Around the corner from Boatyard is Forward Brewing (418 Fourth Street), named for the bow of a boat. It’s at the edge of a residential neighborhood and closes early, 9pm Tuesday-Saturday and 7pm on Sundays.

The granddaddy of boater bars in Annapolis is Davis’ Pub (400 Chester Avenue). The inside is a bit tight and people overflow outside, especially on nice evenings. Davis is the nightly hangout for many of the people who live on their boats docked at the marinas encompassing the peninsula that makes up the Eastport neighborhood. It’s also where boaters head after sailboat races, fishing tournaments, or any other boating event during the season.

Digiprove sealCopyright secured by Digiprove © 2022