Matthew & Madison
Things To Do
Main Street
Stroll down historic Main Street, where you’ll find charming shops and delicious restaurants!
O'Brien's Oyster Bar & Seafood Tavern
Local restaurant located right on main street. Home of Maddie's favorite crab dip!
The Choptank
A waterfront restaurant right next to the Waterfront Hotel offering delicious Maryland seafood and stunning views of the harbor. Perfect for enjoying fresh oysters or a sunset dinner by the water.
DRY 85
If you're a bourbon fan like Matt, you'll love this one!
McGarvey's
A favorite oyster bar right in the heart of Annapolis!
Joss Café & Sushi Bar
Casual sushi restaurant right on Main Street! S/O to Will & Kallie Lyons for introducing us to this favorite!
Chick & Ruth's Delly
Diner home to the "Colossal Food" challenges like the 6 lbs milkshake and 3 lb burger. Maddie loves the oreo shake and commends anyone brave enough to attempt the 6 pounder!
Armel-Leftwich Visitor Center
Steeped in history, the Naval Academy offers beautiful architecture and fascinating tours. It’s a great place to take in Annapolis’s heritage and stunning waterfront.
Watermark Tours, Charters, Cruises
For a unique way to experience the city, hop on a Watermark Water Taxi Tour and enjoy scenic views of Annapolis from the water.