American

Main & Market

For nearly two decades, Main & Market has garnered a reputation for creating delicious fare, artfully presented. That is because you will find passion at the heart of each item on our menu. We are ded...

Seafood

Mason's Famous Lobster Rolls

It’s hard to know what’s real anymore. Or what you can believe in. The world is filled with one distraction after another. We’re bombarded with information, and the line between fact and fiction...

American

Medieval Times Dinner and Tournament

Travel through the mists of time to a forgotten age and tale of devotion, courage and love - at Medieval Times Dinner & Tournament. Surrender to an age of bravery and honor and witness epic battles o...

Crab House

Mike's North

Established in 1958, Mike’s Crab House brings you a mouth-watering waterfront dining experience on the banks of the beautiful South River. We proudly serve our crabs in the finest Chesapeake Bay Tra...

Crab House

Mike's Restaurant & Crabhouse

Established in 1958, Mike's Crab House brings you a mouth-watering waterfront dining experience on the banks of the beautiful South River. We proudly serve our crabs in the finest Chesapeake Bay Tradi...

American

Miss Shirley's Cafe

Award Winning, locally owned, Southern inspired, Breakfast, Brunch & Lunch with a Maryland twist. Specialties: Shrimp & Grits, and Chicken ‘N Waffles. Voted Maryland’s Favorite Restaurant. Seen on...

Seafood

O'Brien's Oyster Bar & Seafood Tavern

Whatever the century or decade, O'Brien's at 113 Main Street Annapolis is the place to be in Downtown. With live entertainment and a great menu boasting authentic Maryland seafood and American cuisine...

Italian

Osteria 177

The Evolution of Coastal Italian-Mediterranean Cuisine! Utilizing the freshest organic ingredients, we specialize in Fresh Seafood, Chops, Pasta, and Seasonal Game. Daily dinner specials. Full bar and...

American

Rams Head Roadhouse

Rams Head Roadhouse opened in 2004 at the former site of Rudy's Tavern off of Generals Highway. A local favorite, Rams Head Roadhouse serves over 40 sandwich and burger combinations, pizza and more. F...

American

Rams Head Tavern

Enjoy great food, cold beer and a friendly atmosphere in our historic English-style pub or cozy dining fireside or outdoors on our Wisteria covered brick patio.  Voted best happy hour & beer selectio...

Wine Bar

Red Red Wine Bar

With a simple Annapolis storefront in 2011, this husband-wife team threw open the doors to the first of their four Maryland restaurants. Brian Bolter was a Washington, DC news anchor. Lisa Bolter spe...

American

Reynolds Tavern

Beautifully restored 1737 tavern in the heart of the Historic District. English Afternoon Tea and a full lunch menu offered seven days a week. Dinner by candlelight Wednesday–Sunday. A must “e...