Madeleine & John
Madeleine & John
Things to Do
Explore Main Street & City Dock
Downtown Annapolis is full of great shopping, wonderful restaurants and fun bars, all hosted in historic buildings. At the very bottom of Main Street is City Dock, a great place to watch boats of all shapes and sizes and for little ones to feed the ducks!
Tour the Maryland State House
The Maryland State House is located in Downtown Annapolis on State Circle. It offers regular tours of the historic landmark and its grounds. The lawn in front of the state house is also a lovely place for a picnic lunch or to let little ones run around.
If you're interested in more historic tours The William Paca House & Gardens and St. John's College are within a few blocks and are also lovely places to explore.
Take a Trolley Tour of Annapolis
There are open air trollies that tour Downtown Annapolis, a great option for those with little ones or who prefer not to walk extensively.
Ride on the Harbor Queen
The Annapolis Harbor Queen & Watermark Tours offer tours on the water of the Chesapeake Bay & Severn River. The tours leave from Downtown Annapolis on a regular schedule and offer indoor (air conditioned) and outdoor seating options.
Places to Eat
Fox's Den
Fantastic wood-fired pizza, local beer and a great atmosphere, located in the basement of a historic building on Main Street.
Address: 179B Main St, Annapolis, MD 21401
Market House
The Market House is located right in the heart of Downtown across from City Dock and offers great, Maryland food options!
Address: 25 Market Space, Annapolis, MD 21401
Preserve
Features Pennsylvania Dutch fair in a modern setting. One of the best restaurants in Annapolis and a great place for dinner, also on Main Street!
Address: 164 Main St, Annapolis, MD 21401
Boatyard Grill
Just across the walkable drawbridge from Downtown Annapolis into Eastport you'll find Boatyard Grill, which offers a fun atmosphere to enjoy great seafood (perfect for brunch!)
Address: 400 Fourth St, Annapolis, MD 21403
O'Leary's Seafood
Some of the best seafood in Annapolis and a great place for a more formal sit down dinner. Also in Eastport, just half a block from the water.
Address: 310 Third St, Annapolis, MD 21403
Chick & Ruth's Deli
An old school greasy-spoon diner with huge portions, located on Main Street. A very well known and well-loved stop and totally kid friendly.
Address: 165 Main St, Annapolis, MD 21401
Places to Get A Drink:
Forward Brewing
A fun local brewery in Eastport with a large selection of local beers in a fun, modern setting.
Address: 418 Fourth Street
Annapolis, Maryland
McGarvey's
A favorite for locals and tourists alike, McGarvey's is a restaurant during the day and a very popular bar at night. Located just across from the Market House & City Dock.
Address: 8 Market Space, Annapolis, MD 21401
Ram's Head Live
Located just off State Circle on West Street, Ram's Head frequently books great live music, has great beer + spirits, decent food and tons of seating.
Address: 33 West St, Annapolis, MD 21401
Pussser's
A famous stop in downtown Annapolis, Pusser's is a popular bar located right on the water.
Address: 80 Compromise St, Annapolis, MD 21401