Best Pubs and Taverns in Annapolis (Self Guided), Annapolis
America’s Sailing Capital, Annapolis, has no shortage of exciting places where locals and visitors alike can enjoy great beer and seafood till late at night. For extra fun, on top of regular treats, the majority of local pubs, saloons, and bars host live music shows on a regular basis, as well as different contests.
Galway Bay Irish Pub, nestled in the heart of downtown, offers an authentic Irish experience with traditional music, hearty food, and a wide selection of drinks. McGarvey's Saloon & Oyster Bar is another popular spot known for its laid-back atmosphere and fresh seafood. Middleton Tavern, a historic establishment dating back to 1750, exudes charm and sophistication, serving delicious regional dishes and signature cocktails.
Dock Street Bar & Grill is a favorite among locals for its waterfront location and delicious pub fare, perfect for enjoying views of the harbor. Castlebay Irish Pub channels the spirit of Ireland with its cozy interior, friendly staff, and extensive beer selection.
Rams Head Tavern, further along, offers a diverse menu and live entertainment, making it a hotspot for nightlife in Annapolis. Finally, just steps away from it, Stan and Joe's Saloon is a beloved neighborhood haunt known for its casual vibe, tasty comfort food, and lively crowd.
Whether you're a local or just passing through, be sure to stop by one (if not all!) of these iconic establishments and immerse yourself in the warm hospitality of Annapolis. Your taste buds will thank you for that! Just gather your friends, raise a glass, and enjoy yourself. Cheers to unforgettable memories and good times in Annapolis, Maryland!
Galway Bay Irish Pub, nestled in the heart of downtown, offers an authentic Irish experience with traditional music, hearty food, and a wide selection of drinks. McGarvey's Saloon & Oyster Bar is another popular spot known for its laid-back atmosphere and fresh seafood. Middleton Tavern, a historic establishment dating back to 1750, exudes charm and sophistication, serving delicious regional dishes and signature cocktails.
Dock Street Bar & Grill is a favorite among locals for its waterfront location and delicious pub fare, perfect for enjoying views of the harbor. Castlebay Irish Pub channels the spirit of Ireland with its cozy interior, friendly staff, and extensive beer selection.
Rams Head Tavern, further along, offers a diverse menu and live entertainment, making it a hotspot for nightlife in Annapolis. Finally, just steps away from it, Stan and Joe's Saloon is a beloved neighborhood haunt known for its casual vibe, tasty comfort food, and lively crowd.
Whether you're a local or just passing through, be sure to stop by one (if not all!) of these iconic establishments and immerse yourself in the warm hospitality of Annapolis. Your taste buds will thank you for that! Just gather your friends, raise a glass, and enjoy yourself. Cheers to unforgettable memories and good times in Annapolis, Maryland!
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Best Pubs and Taverns in Annapolis Map
Guide Name: Best Pubs and Taverns in Annapolis
Guide Location: USA » Annapolis (See other walking tours in Annapolis)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 7
Tour Duration: 1 Hour(s)
Travel Distance: 1.2 Km or 0.7 Miles
Author: AudreyB
Sight(s) Featured in This Guide:
Guide Location: USA » Annapolis (See other walking tours in Annapolis)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 7
Tour Duration: 1 Hour(s)
Travel Distance: 1.2 Km or 0.7 Miles
Author: AudreyB
Sight(s) Featured in This Guide:
- Galway Bay Irish Pub
- McGarvey's Saloon & Oyster Bar
- Middleton Tavern
- Dock Street Bar & Grill
- Castlebay Irish Pub
- Rams Head Tavern
- Stan and Joe's Saloon
1) Galway Bay Irish Pub
Galway Bay Irish Pub is a restaurant and bar inspired by traditional pubs in Ireland. It opened in December 1998 and was founded by Michael Galway and Anthony Clarke. From the beginning, the idea was to create a place where people could gather for simple meals, conversation, and music, similar to neighborhood pubs in Ireland. Today it attracts both local residents and visitors exploring the nearby harbor and historic landmarks.
Inside, the pub has the feel of a traditional Irish tavern. Exposed brick walls, warm wood finishes, and stained glass details create a comfortable setting for food and drinks. Wooden tables fill the dining area, and many guests sit at the long bar to talk and enjoy a drink. The walls display Irish signs, photographs, and memorabilia. Televisions are generally absent, encouraging conversation among guests.
The menu includes Irish dishes such as shepherd’s pie, bangers and mash, Irish stew, and fish and chips. Local seafood is also served, including Maryland crab cakes and cream of crab soup. The bar offers Irish beers and whiskies, with Guinness poured in the traditional way. Live Irish folk music and trivia nights are regular events, and the pub becomes especially busy during St. Patrick’s Day celebrations.
Inside, the pub has the feel of a traditional Irish tavern. Exposed brick walls, warm wood finishes, and stained glass details create a comfortable setting for food and drinks. Wooden tables fill the dining area, and many guests sit at the long bar to talk and enjoy a drink. The walls display Irish signs, photographs, and memorabilia. Televisions are generally absent, encouraging conversation among guests.
The menu includes Irish dishes such as shepherd’s pie, bangers and mash, Irish stew, and fish and chips. Local seafood is also served, including Maryland crab cakes and cream of crab soup. The bar offers Irish beers and whiskies, with Guinness poured in the traditional way. Live Irish folk music and trivia nights are regular events, and the pub becomes especially busy during St. Patrick’s Day celebrations.
2) McGarvey's Saloon & Oyster Bar
McGarvey’s Saloon & Oyster Bar opened on June 19, 1975. It was founded by retired Air Force Captain Michael Ashford. The name “McGarvey” comes from Ashford’s family history. It was his grandmother’s maiden name, and he later registered it in memory of a great-uncle, Manus McGarvey, who worked as a streetcar conductor in Chicago. Over the years, the restaurant became a well-known gathering place for residents, sailors, and visitors spending time near the harbor.
Inside, the restaurant has the feel of a traditional saloon, with a long wooden bar, simple tables, and nautical decorations. A notable feature is the collection of military flight helmets donated by customers, reflecting the area’s strong naval and aviation ties. More than 100 marriage plates are also displayed, honoring couples who had their first date here and later married.
The menu focuses on seafood connected to Chesapeake Bay traditions. Fresh oysters and crab cakes are among the most popular dishes. The restaurant is also known for regional soups such as Maryland crab soup and cream of crab soup. Many visitors stop here for a meal or a drink while exploring the harbor area, and the restaurant often stays busy, especially during the warmer months when people gather near the waterfront.
Inside, the restaurant has the feel of a traditional saloon, with a long wooden bar, simple tables, and nautical decorations. A notable feature is the collection of military flight helmets donated by customers, reflecting the area’s strong naval and aviation ties. More than 100 marriage plates are also displayed, honoring couples who had their first date here and later married.
The menu focuses on seafood connected to Chesapeake Bay traditions. Fresh oysters and crab cakes are among the most popular dishes. The restaurant is also known for regional soups such as Maryland crab soup and cream of crab soup. Many visitors stop here for a meal or a drink while exploring the harbor area, and the restaurant often stays busy, especially during the warmer months when people gather near the waterfront.
3) Middleton Tavern
Middleton Tavern is a historic restaurant whose story goes back to around 1750. The building was constructed by Horatio Middleton, a local merchant involved in trade along the Chesapeake Bay. In the eighteenth century, the busy harbor nearby brought sailors, traders, and travelers to the area. Taverns like this one were important places where people could eat, rest, and exchange news about business and politics.
Over time the tavern became connected with several well-known figures from early American history. Records link it with visitors such as George Washington, Thomas Jefferson, and Benjamin Franklin. During the years around the American Revolution, taverns like this often served as meeting places where officials, merchants, and residents gathered to talk and share news.
The building keeps features typical of eighteenth-century port architecture, including brick walls and tall windows. Inside are several dining rooms and bar areas on different levels, with wooden beams and fireplaces. Today the tavern serves casual meals such as crab cakes, oysters, soups, and sandwiches, continuing a tradition that has lasted for more than two centuries.
Over time the tavern became connected with several well-known figures from early American history. Records link it with visitors such as George Washington, Thomas Jefferson, and Benjamin Franklin. During the years around the American Revolution, taverns like this often served as meeting places where officials, merchants, and residents gathered to talk and share news.
The building keeps features typical of eighteenth-century port architecture, including brick walls and tall windows. Inside are several dining rooms and bar areas on different levels, with wooden beams and fireplaces. Today the tavern serves casual meals such as crab cakes, oysters, soups, and sandwiches, continuing a tradition that has lasted for more than two centuries.
4) Dock Street Bar & Grill
Dock Street Bar & Grill is a casual restaurant and bar located near the harbor, a short walk from the busy waterfront where boats regularly pass through an area known as Ego Alley. The building once served as the Annapolis City Jail and later became a restaurant and tavern that attracts both visitors and locals. Many people stop here while walking around the harbor or after spending time on the water, especially during the busy boating season.
The menu includes American bar food and Chesapeake Bay seafood such as crab cakes, crab chowder, steamed shrimp, and fish and chips. Burgers, wings, pizzas, sandwiches, and salads are also served. The bar offers bottled and canned beer, wine, and cocktails, and outdoor tables overlook the harbor and passing boats in Ego Alley.
Inside, the restaurant has a relaxed tavern atmosphere with nautical decorations, sailing pictures, and maritime memorabilia. The space has two levels with areas for dining and socializing. During the day, large windows bring in natural light, while evenings become livelier as people gather for drinks. Televisions show sports events, and on some weekends the upper level hosts dancing and DJ music.
The menu includes American bar food and Chesapeake Bay seafood such as crab cakes, crab chowder, steamed shrimp, and fish and chips. Burgers, wings, pizzas, sandwiches, and salads are also served. The bar offers bottled and canned beer, wine, and cocktails, and outdoor tables overlook the harbor and passing boats in Ego Alley.
Inside, the restaurant has a relaxed tavern atmosphere with nautical decorations, sailing pictures, and maritime memorabilia. The space has two levels with areas for dining and socializing. During the day, large windows bring in natural light, while evenings become livelier as people gather for drinks. Televisions show sports events, and on some weekends the upper level hosts dancing and DJ music.
5) Castlebay Irish Pub
Castlebay Irish Pub is a small restaurant that brings Irish food and pub traditions to the historic waterfront district. It opened in 1998 and was founded by Vincent Quinlan, a native of Dublin, Ireland, who wanted to recreate the atmosphere of a traditional Dublin pub. Since then, it has become a popular place where locals and visitors stop for a meal, a drink, or live music.
The interior resembles a traditional Irish pub, with dark mahogany wood, stained glass, and moss-green walls. The menu includes Irish dishes such as shepherd’s pie, fish and chips, and lamb stew, along with regional seafood like Maryland crab cakes and cream of crab soup. The bar also serves Irish whiskies and beers, including Guinness poured in the traditional style.
Music and social events are an important part of the pub’s atmosphere. Live Irish folk music is often played in the evenings, and karaoke nights are also held regularly. The pub becomes especially busy around St. Patrick’s Day, when many people gather before and after parade celebrations and the doors often open early. Its small size and relaxed setting give it the feel of a neighborhood pub where visitors can enjoy food, music, and conversation.
The interior resembles a traditional Irish pub, with dark mahogany wood, stained glass, and moss-green walls. The menu includes Irish dishes such as shepherd’s pie, fish and chips, and lamb stew, along with regional seafood like Maryland crab cakes and cream of crab soup. The bar also serves Irish whiskies and beers, including Guinness poured in the traditional style.
Music and social events are an important part of the pub’s atmosphere. Live Irish folk music is often played in the evenings, and karaoke nights are also held regularly. The pub becomes especially busy around St. Patrick’s Day, when many people gather before and after parade celebrations and the doors often open early. Its small size and relaxed setting give it the feel of a neighborhood pub where visitors can enjoy food, music, and conversation.
6) Rams Head Tavern
Rams Head Tavern opened in 1989 when Bill and Paula Muehlhauser purchased the property and developed it into a small pub and restaurant. At first it was a small pub with about 30 seats, serving food and drinks in a casual setting. Over time it grew in popularity and became a regular gathering place for meals, conversation, and evening entertainment.
Live music became a larger focus in 1997 when the owners opened Rams Head On Stage, a concert venue connected with the tavern. The room holds about 300 people and is fully seated, with tables placed close to the stage so audiences can watch performers from a short distance. The small size creates a more personal concert experience than a typical theater.
The tavern continues to operate as both a restaurant and a music destination. The menu includes familiar American dishes such as burgers, sandwiches, salads, and seafood. Concerts take place regularly at Rams Head On Stage, featuring touring musicians, tribute bands, comedians, and local performers. Together, the restaurant and the performance space offer visitors a place to enjoy food, drinks, and live entertainment in one evening.
Live music became a larger focus in 1997 when the owners opened Rams Head On Stage, a concert venue connected with the tavern. The room holds about 300 people and is fully seated, with tables placed close to the stage so audiences can watch performers from a short distance. The small size creates a more personal concert experience than a typical theater.
The tavern continues to operate as both a restaurant and a music destination. The menu includes familiar American dishes such as burgers, sandwiches, salads, and seafood. Concerts take place regularly at Rams Head On Stage, featuring touring musicians, tribute bands, comedians, and local performers. Together, the restaurant and the performance space offer visitors a place to enjoy food, drinks, and live entertainment in one evening.
7) Stan and Joe's Saloon
Stan and Joe’s Saloon is a bar and restaurant that has been part of the local nightlife since January 2007. It was opened by Stan Fletcher and Joe McGovern, often called “Little Joe,” two longtime local bartenders who created a casual place for residents, students, and visitors. Since then, it has grown into a well-known neighborhood spot while keeping a relaxed and friendly atmosphere.
Inside, there are several bar areas and rooms with tables where people gather to eat, drink, and watch sports. Televisions are placed throughout the space, making it a common place for watching football, baseball, basketball, and other games. One long-standing tradition is gathering here to watch the Baltimore Ravens play. During important games, the rooms often fill with fans wearing team colors and cheering together.
The menu includes familiar bar food such as burgers, wings, sandwiches, nachos, and seafood inspired by the Chesapeake Bay region. Visitors can choose from draft beers, cocktails, and other drinks. In the evenings, the saloon often hosts live bands, DJs, and karaoke nights. In February 2026, it marked its 19th anniversary, showing how it has remained a regular meeting place for food, music, and a night out.
Inside, there are several bar areas and rooms with tables where people gather to eat, drink, and watch sports. Televisions are placed throughout the space, making it a common place for watching football, baseball, basketball, and other games. One long-standing tradition is gathering here to watch the Baltimore Ravens play. During important games, the rooms often fill with fans wearing team colors and cheering together.
The menu includes familiar bar food such as burgers, wings, sandwiches, nachos, and seafood inspired by the Chesapeake Bay region. Visitors can choose from draft beers, cocktails, and other drinks. In the evenings, the saloon often hosts live bands, DJs, and karaoke nights. In February 2026, it marked its 19th anniversary, showing how it has remained a regular meeting place for food, music, and a night out.
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