When you’re in Annapolis, Maryland, looking for the best happy hours to unwind after a long day, there are several enticing options that might just pique your interest. From waterfront settings to cozy atmospheres, the variety of bars and restaurants offering great deals on drinks and appetizers is sure to cater to your preferences. So, if you’re curious to discover which spot stands out as the ultimate happy hour destination in Annapolis, keep on exploring to uncover the hidden gem waiting for you.

Looking to raise a glass without breaking the bank in Annapolis, Maryland? Look no further! We’ve rounded up the top best happy hour spots in this charming Annapolis area waterfront city where you can enjoy good deals on drinks and bites. Whether you’re a local looking for a new spot or just passing through, these savings will have you saying cheers in no time! 

MCGARVEY’S

If you find yourself in Annapolis, Maryland looking for a spot to unwind with great deals on drinks and delicious bites, head over to McGarvey’s for their fantastic happy hour specials.During their happy hour, which runs from Monday to Friday, 2:00-6:00 PM, you can enjoy $5 wines, beers, and single liquor drinks. Known for serving the best cheeseburgers, oysters, and crab balls in town, McGarvey’s also offers signature appetizers like crab dip for only $8.The cozy atmosphere between Middleton Tavern and the historic Shiplap House creates the perfect setting for you to relax and socialize while indulging in local oysters and small plates. Pair your crab dip with a glass of red wine for the ultimate happy hour experience at McGarvey’s. Don’t miss out on this hidden gem in Annapolis where you can savor delectable dishes and refreshing drinks at unbeatable prices.

SEVERN INN

Continuing your exploration of happy hour spots in Annapolis, Maryland, venture over to Severn Inn for a picturesque dining experience with food and drink specials that will surely delight your taste buds. Overlooking the stunning Chesapeake Bay in downtown Annapolis, Severn Inn offers a perfect setting for unwinding after a long day. During their happy hours, indulge in fresh oysters for just $1 each and savor the flavor of grilled sweet chili wings. Quench your thirst with beer specials featuring Abita for $3.95 and Natty Boh for $2.95, or enjoy a glass of select wine for $6.95. The elegant wall of windows at Severn Inn provides sweeping views, creating a scenic backdrop for your evening. Make the most of your weekdays from Monday to Friday, 3:00-6:00 PM, by taking advantage of Severn Inn’s daily specials and relaxing in this charming waterfront setting.

PUSSER’S

Nestled along the waterfront in Annapolis, Pusser’s Caribbean Grille beckons with its vibrant atmosphere and tantalizing Caribbean-inspired cuisine. This waterfront restaurant is a gem for happy hour enthusiasts, offering a delightful selection of drinks and appetizers at special prices. As you unwind with a refreshing beverage, take in the stunning views of the harbor that add to the charm of the experience. Pusser’s is renowned for its authentic Caribbean flavors, allowing you to savor the essence of the islands right in Annapolis. Don’t miss out on trying their signature Painkiller cocktail, a true delight for your taste buds. The Rum Bar at Pusser’s adds to the allure, offering a wide range of rum selections to complement your Caribbean culinary journey. The lively atmosphere, complete with live music events, enhances the overall dining experience. Whether you choose to sit indoors or opt for outdoor seating, Pusser’s provides a relaxing ambiance perfect for enjoying sunsets and creating unforgettable memories.

THE POINT

The Point offers a variety of discounted drinks and appetizers during its lively happy hour, making it a popular choice for locals and visitors in Annapolis. You can indulge in 1/2 priced appetizers, $2 Domestic drafts, and $3.50 craft/import drafts, perfect for unwinding after a long day.

If you’re a wine lover, make sure to visit during Wine O-Wednesdays to enjoy 1/2 price bottles of House Wine and enjoy your favorite glasses of wine at a great price.  The atmosphere at The Point is enhanced with live music every Wednesday and Thursday from 5:00-8:00 PM, adding a vibrant touch to your evening.

Additionally, take advantage of $1 off rail drinks and $5 house wines to complement your appetizers. Sit back and relax in the water-side experience that The Point provides, with both inside and outside seating options available, allowing you to enjoy your drinks and food while taking in the beautiful views.

It’s the ideal spot to unwind and socialize in Annapolis.

SAILOR OYSTER BAR

Tucked away in Annapolis, Maryland, Sailor Oyster Bar beckons oyster enthusiasts with its cozy ambiance and fresh seafood offerings. This charming oyster bar features local oysters sourced from the Chesapeake Bay, ensuring a true taste of the region. The dining areas at Sailor Oyster Bar provide a welcoming setting to indulge in these delectable treats while sipping on signature cocktails crafted with care.

During happy hours at Sailor Oyster Bar, which run from Tuesday to Friday between 4-5:30pm and on Saturdays from 12-3pm, you can enjoy these local oysters at a great value. The menu goes beyond just oysters, offering an array of sandwiches, charcuterie options, and a diverse selection of cocktails to complement your dining experience. The relaxed atmosphere and exceptional service make Sailor Oyster Bar a top choice among locals and visitors alike for unwinding after a long day.

BLACKWALL HITCH

With its vibrant waterfront location and diverse menu, Blackwall Hitch in Annapolis, Maryland, offers a sophisticated dining experience for both locals and tourists alike. This upscale establishment is known for its stunning views of the harbor and marina, making it a perfect spot to unwind during happy hours.

Indulge in their fresh seafood dishes while sipping on handcrafted cocktails that are sure to tantalize your taste buds. The lively atmosphere at Blackwall Hitch is further elevated with live music, creating a welcoming environment for socializing and relaxing after a long day.

Whether you’re a seafood enthusiast or a cocktail connoisseur, this modern and stylish setting caters to a wide range of preferences, making it a popular choice among Annapolis visitors. Don’t miss out on the opportunity to experience the charm and elegance that Blackwall Hitch has to offer during your next happy hour outing.

RED RED WINE BAR

Step into Red Red Wine Bar in downtown Annapolis and immerse yourself in a world of exquisite wines and inviting ambiance. This cozy bar caters to wine enthusiasts with its extensive selection of wines available by the glass or bottle.If you’re looking to expand your wine knowledge, Red Red Wine Bar hosts wine tastings and events where you can explore different varietals in a welcoming setting. During their happy hours, you can enjoy discounted wine flights paired with delicious small plates, making it the perfect spot to unwind after a long day or catch up with friends. Located in the heart of downtown Annapolis, this popular wine bar is known for its cozy atmosphere and excellent selection. Whether you’re a seasoned wine connoisseur or just starting to develop your palate, Red Red Wine Bar offers a delightful experience for all wine lovers.

METROPOLITAN KITCHEN & LOUNGE

Indulge in vibrant cocktails and creative small plates at Metropolitan Kitchen & Lounge, a popular happy hour spot in Annapolis with a trendy and modern setting. This Annapolis gem offers discounted craft cocktails, beers, and wines during happy hours, catering to a variety of drink preferences. Situated in the heart of Annapolis, Metropolitan Kitchen & Lounge sets the stage for a lively and social happy hour experience. The happy hour menu at this hotspot focuses on creative and delicious small plates, providing a perfect accompaniment to your drinks.As you sip on your favorite cocktail, enjoy the energetic ambiance enhanced by live music performances and a bustling social scene. Metropolitan Kitchen & Lounge truly captures the essence of Annapolis’s vibrant happy hour scene, offering a perfect blend of craft cocktails, tasty small plates, and live music in a modern setting. Experience the best of Annapolis’s nightlife at this must-visit happy hour destination.

DAVIS’ PUB

Since the 1920s, locals in Annapolis have cherished Davis’ Pub as a neighborhood favorite known for its creative pub fare and renowned crab cakes. Whether you’re a local looking for the best happy hours or just visiting, Davis’ Pub offers a cozy and welcoming atmosphere to enjoy some delicious food and drinks. Their menu features not only their famous crab cakes but also other tasty options like crab balls, Pub Tots, Chicken and Sausage Gumbo, and Buffalo Chicken Salad. While some mixed reviews on food quality post-COVID exist, Davis’ Pub remains a popular spot, especially for their crab pretzels and crab dip. Plus, if it’s your second time in Annapolis, returning to Davis’ Pub for happy hour is a must to experience the local favorite dishes and vibe that keeps patrons coming back for more. So, head over to Davis’ Pub for a laid-back and enjoyable happy hour experience in Annapolis.

FOX’S DEN

Nestled in the heart of Annapolis, Fox’s Den offers a unique and inviting happy hour experience with special discounts on select drinks and appetizers. The cozy atmosphere at Fox’s Den sets the perfect backdrop for unwinding after a long day. You’ll find yourself drawn in by the warm ambiance as you settle in for a delightful evening. During happy hour, indulge in a variety of small plates that are perfect for sharing with friends or enjoying solo. The handcrafted cocktails at Fox’s Den are a must-try, expertly prepared to tantalize your taste buds with each sip.Located conveniently in Annapolis, Fox’s Den is a popular spot for those seeking a laid-back vibe and exceptional service. Whether you’re a local resident or just passing through, Fox’s Den offers a welcoming environment where you can relax and enjoy the best that Annapolis has to offer during happy hour.

Galway Bay

Galway Bay, an authentic Irish restaurant and pub in the heart of Annapolis, offers a cozy and welcoming atmosphere for patrons seeking traditional Irish dishes and brews. If you’ve had a long day and crave a taste of Ireland, this is the spot for you.Away from the bustling city, Galway Bay provides a sanctuary where you can unwind with a pint of Guinness and indulge in classic Irish fare like cod fish and sailor oysters. Live music performances on weekends add to the vibrant ambiance, enhancing your overall experience. To ensure you secure a table, it’s advisable to call ahead, especially during peak hours. Customers rave about the quality of the Guinness pours and the authentic Irish coffee, immersing you in true Irish hospitality.

Dry85

Dry85, a popular spot in Annapolis, offers a unique and creative cocktail experience for its patrons. Located on Main Street, this establishment attracts a bustling crowd in Eastport, where locals and visitors gather to enjoy the diverse selection of artisanal cocktails during happy hour.The happy hour at Dry85 provides an opportunity to savor affordable drink specials while indulging in the lounge’s range of small plates that perfectly complement the cocktail offerings. With a focus on eco-friendly American cuisine, Dry85’s stylish setting creates a welcoming atmosphere for those looking to unwind and socialize on the Eastern Shore. Whether you’re a cocktail connoisseur or simply looking for a happy hour spot with a distinctive charm, Dry85 promises to deliver a memorable experience in the heart of Annapolis.

Downstairs bar at Rams Head

For a cozy and intimate happy hour experience in Annapolis, head over to Down bar at Rams Head, where you can enjoy an extensive selection of craft beers and specialty cocktails in a relaxed atmosphere. This charming spot is known for its welcoming ambiance, making it the perfect place to unwind with friends or colleagues after a long day. During happy hour, you can indulge in discounted appetizers and drink specials while socializing and enjoying the laid-back vibe. Located in the heart of Annapolis, Down bar at Rams Head is a convenient spot for both locals and visitors to gather and enjoy great company along with fantastic deals.Whether you’re a craft beer enthusiast or a cocktail connoisseur, this venue has something to offer everyone looking for a memorable happy hour experience in the city. So, grab a seat, sip on a refreshing drink, and savor the moment at Down bar at Rams Head.

Boatyard Bar & Grill

Nestled along the waterfront in Annapolis, Boatyard Bar & Grill beckons with its nautical theme and delectable seafood offerings. This popular spot is a favorite among locals and visitors alike, known for its wide selection of craft beers, cocktails, and stunning harbor views from its outdoor seating area. On weekends, live music events enhance the vibrant atmosphere of Boatyard Bar & Grill. The menu features fresh seafood options and local favorites, with rave reviews particularly praising their crab cakes and fish tacos. If you’re looking for a family-friendly and lively environment, this spot is perfect for casual dining and socializing in a laid-back setting. Whether you’re craving a refreshing drink after work or a delicious seafood dinner with friends, Boatyard Bar & Grill delivers on both fronts, making it a must-visit during happy hour in Annapolis. This is also a great spot for Sunday Brunch.

Iron Rooster

Iron Rooster offers a unique dining experience with a focus on breakfast and brunch, featuring a twist on traditional American comfort food. Known for their famous homemade pop tarts in flavors like strawberry, brown sugar cinnamon, and s’mores, this eatery provides a lively and inviting atmosphere with rustic decor and cozy seating options.Indulge in their signature cocktails, including popular choices like Bloody Marys and mimosas, while exploring a diverse menu that caters to all dietary preferences, including gluten-free and vegetarian choices. Whether you’re craving a hearty breakfast or a leisurely brunch, Iron Rooster has something for everyone.The restaurant’s vibrant ambiance and delicious offerings make it a must-visit spot in Annapolis, Maryland. Treat yourself to a delightful culinary experience at Iron Rooster, where comfort food gets a creative and flavorful upgrade.

Conclusion

So next time you’re in Annapolis, make sure to check out these amazing happy hour spots for great deals on drinks and delicious food.

Whether you prefer a cozy pub atmosphere or a lively waterfront setting, there’s something for everyone to enjoy in this charming city.

Don’t miss out on these fantastic happy hour specials in Annapolis, Maryland!