Food

Outdoor activities such as boating, fishing, kayaking, and biking are a quintessential part of the Annapolis culture during the warmer months. Among that list is also outdoor dining. Several restaurants around town have a few tables on the sidewalk that makes for a relaxing environment and prime people watching, but these top six restaurants prioritize dining al fresco.

Metropolitan Kitchen & Lounge

Outdoor Dining in Annapolis
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West Street has become a place for visitors and locals alike to congregate, share a meal and indulge in the nightlife. Metropolitan Kitchen and Lounge, or ‘Metro’ (as the locals say) has become a landmark due to its popular music offerings, diverse menu and scenic rooftop. As the only rooftop restaurant on West Street, it’s a popular space for dining or just enjoying a cocktail while listening to live music. The open-air space is also available to host private events, from dinner parties to happy hours. Although you can’t quite see the Chesapeake from Metro’s rooftop, the view of the city is the perfect backdrop for dining outside on West Street. 175 West St., (410) 280-5160

Reynolds Tavern and 1747 Pub

Outdoor Dining in Annapolis
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The 1747 Pub is a classic Annapolis restaurant and the watering hole located on Church Circle. The cozy, candle-lit feel of the lower-level establishment is great for the colder months, but as it warms up, patrons make their way to the adjacent courtyard patio. This shady extension to the pub is a go-to spot especially when you’re in the mood for a special event to accompany the outdoor dining experience. Reynolds has a summer schedule packed with a trivia night, burger and drink specials, Shakespeare performances and a movie night. 7 Church Circle, (410) 295-9555

Carrol’s Creek Cafe

Outdoor Dining in Annapolis
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Carrol’s Creek Cafe is about as authentic Annapolis as they come. This fine-dining restaurant offers an upscale ambiance with a down-to-earth menu that appeals to everyone. Their waterfront location in Eastport allows diners to watch boaters, kayakers and paddle boarders cruising along the water as they enjoy fresh, local fare. Check out the blog post featuring Carrol’s Creek Cafe to learn more. 410 Severn Ave #100, (410) 263-8102

Blackwall Hitch

Outdoor Dining in Annapolis
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Eastport is known for its low-key, local scene. Blackwall Hitch sees their vibe and takes it to the next level with a culinary flair that sets them apart from the pack. In addition to a vibrant, Chesapeake-inspired menu, the rooftop patio is the only one in Eastport. The view of the water and downtown Annapolis is perfect for events like Fourth of July fireworks, sailboat races or simply a sunny Sunday afternoon. Blackwall’s rooftop patio is also available for private events. 400 Sixth Street, 410-263-3454

Pusser’s Caribbean Grille

Outdoor Dining in Annapolis
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There’s nothing better than feeling like you’re on vacation in your own backyard. Pusser’s is one of the few dock bars in Annapolis and it’s a hot spot. Whether arriving by land or sea, Pusser’s restaurant and dock bar instantly transports you to the land of coconut shrimp and living on island time, but of course with a Maryland food and cocktail twist. There’s no shortage of entertainment thanks to live music on the dock and a front seat view of Ego Alley. Pusser’s is the epicenter for outdoor dining right on the water. 80 Compromise Street, (410) 626-0004

Dinner Under the Stars

Outdoor Dining in Annapolis
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A more recent summertime dining favorite is the weekly event Dinner Under the Stars when West Street is closed to cars and the restaurant populate the street with tables. The community gathers to eat, drink and dance the night away under twinkling lights. Six restaurants in the block participate in the event and offer a wide variety of options from Mexican at El Toro Bravo to sushi at Tsunami, to American favorites at Stan & Joe’s Saloon and 49 West. If your looking for an even heartier option be sure to try out Luna Blu Restorante Italiano. As everyone eats and relaxes, the sound of live bands playing popular favorites fills the air and adds to the warm summer night energy – Rams Head Tavern serves food and even more music inspiration as well! West Street between Calvert Street and Church Circle.

Rooftops, courtyard patios, dockside and filling the streets, this nautical town doesn’t disappoint when it comes to making the most of warm weather. Summer can fly by, so be sure to enjoy the outdoor dining while it lasts!

Kristin Dyak

Kristin Dyak is the digital marketing director at a local ad agency where she specializes in social media marketing. She became an Annapolitan in 2015 when moving back east after a stint on the west coast. Growing up in Northern Virginia, Annapolis and the Eastern Shore were home to countless childhood, summer memories. Kristin is excited to be part of a vibrant neighborhood that prioritizes local artists, music and events that encourage a progressive community in this historic city.