Historic brownstone district around the Washington Monument, home to The Helmand, The Prime Rib and a long line of immigrant kitchens on Charles Street.
The Helmand on Charles Street has cooked Afghan food in Mount Vernon since 1989, known for its kaddo borawni baby pumpkin and aushak dumplings.
Signature: Kaddo borawni, Aushak, Lamb kebab
Order: Start with the kaddo borawni; few first courses in the city are as well-loved.
Tip: It is a Mount Vernon institution and books up on weekends; reserve ahead for dinner.
Magdalena inside the Ivy Hotel is chef Scott Bacon's seasonal American bistro, plating a changing canape board and Chesapeake plates in a stone mansion.
Order: Whatever lands on the changing canape board, then a seasonal main.
Tip: It sits inside the Relais and Chateaux Ivy Hotel; reserve for the courtyard in warm months.
The Prime Rib in Mount Vernon is a 1940s-style supper club with leopard carpet and a piano, serving the city's benchmark prime rib in black tie.
Order: The prime rib, with the Greenberg potato skins.
Tip: Jackets are required for men; a pianist plays nightly in the lounge.
Sotto Sopra on Charles Street in Mount Vernon plates house-made pasta and an opera-night supper, a long-running Italian room with a deep wine list.
Signature: House-made pasta, Opera-night dinner, Branzino
Order: A plate of the house-made pasta, plus the branzino when it runs.
Tip: The monthly opera nights are the room's signature; reserve well ahead for those.
Dooby's in Mount Vernon is an all-day Korean-leaning cafe, plating breakfast sandwiches by day and a ramen and Korean dinner menu after dark.
Signature: Breakfast sandwich, Ramen, Korean dinner plates
Order: The breakfast sandwich early, or a bowl of ramen later in the day.
Tip: It is part cafe, part bistro; the daytime counter and evening dinner service feel like two places.
Dooby's on Charles Street works as a daytime coffee bar in Mount Vernon, pulling espresso and plating breakfast sandwiches before Korean dinner service.
Signature drink: Coffee and breakfast sandwiches
Tip: The daytime cafe and evening bistro feel like two places; the morning coffee crowd is its own scene.
Ceremony Coffee's Mount Vernon cafe sits in the Marketplace, a bright bar pulling single-origin espresso and filter from the Annapolis roaster's own beans.
Signature drink: Single-origin espresso
Tip: It is the busiest Ceremony in the city; the bar pulls a clean, modern espresso.
The Bun Shop on Read Street in Mount Vernon is an all-day cafe and pastry counter, pulling espresso and serving filled buns, kolaches and pastries late.
Tip: It keeps long hours and pours wine and beer in the evening, not just coffee and pastry.
Worth the queue: Sweet and savoury filled buns
Ceremony Coffee Roasters runs a flagship cafe in Mount Vernon Marketplace, an Annapolis roaster pouring single-origin espresso and filter from its own beans.
Tip: The Mount Vernon Marketplace cafe is the city's busiest Ceremony; the bar pulls a clean espresso.
Sources from: Ethiopia, Colombia, Guatemala
How they serve: Espresso, Filter, Whole bean retail
Sugarvale in Mount Vernon is an intimate basement cocktail bar, mixing inventive, balanced drinks with zero pretension off a frequently changing menu.
Signature drink: Inventive seasonal cocktails
Food: Bar snacks
Tip: It is small and below street level; arrive early on weekends to land a seat at the bar.
The Owl Bar in the Belvedere Hotel is a Mount Vernon landmark since 1903, a wood-panelled former speakeasy with terracotta owls and brick-oven pizza.
Signature drink: Classic cocktails
Food: Brick-oven pizza, pub plates
Tip: The neon owls signalled bootleg liquor in Prohibition days; the brick-oven pizza is the kitchen's strength.
Wet City in Mount Vernon is a brewery, full bar and kitchen in one, pouring house beers and a curated guest list alongside tacos in a colourful upstairs room.
Signature drink: House and guest craft beer
Food: Tacos, bar food
Tip: It brews its own and pours a sharp guest list; the upstairs bar and the tacos are the draw.
The Helmand in Mount Vernon keeps its vegetarian Afghan plates and the kaddo borawni pumpkin gentle on the wallet, a cheap way into a celebrated kitchen.
Try: Vegetarian Afghan plates
Tip: The vegetarian dishes and the kaddo borawni are the value plays at this Mount Vernon room.
Dooby's in Mount Vernon runs an all-day cafe brunch of breakfast sandwiches and Korean-leaning plates, a reliable mid-morning stop on Charles Street.
Order: The breakfast sandwich with a cup of drip.
Tip: The breakfast sandwich is the daytime draw; the kitchen shifts to a Korean dinner menu by night.
Topside crowns Hotel Revival on the 14th floor in Mount Vernon, a rooftop bar and kitchen with some of the city's widest views over the Washington Monument.
Tip: Go at golden hour for the Mount Vernon and harbour views; reserve a window table.
The Drinkery in Mount Vernon is a long-standing LGBTQ dive bar, a no-frills neighbourhood room open nightly with strong, cheap pours and a loyal crowd.
Tip: It is a true dive, open late and cash-friendly; a Mount Vernon mainstay for decades.