Annapolis is steeped in history, its downtown area a virtual museum. Virtually every place you go in downtown Annapolis has historic roots; if you dig hard enough you’ll find them.

The same applies to our local restaurants. For a hefty serving of history with your meal, try one of these three dining establishments in historic Annapolis. 


This historic building at 2 Market Space at City Dock dates back to 1750 and is believed to be the oldest continuously operating tavern in the United States. It is said that George Washington, Thomas Jefferson and Benjamin Franklin enjoyed Middleton Tavern’s hospitality – a reputation that persists today under current owner (since 1968) and entrepreneur Jerry Hardesty. Hardesty restored the building’s exterior and interior, making it a handsome downtown landmark favored for its outdoor patio, Sunday brunches, extensive seafood menu, and live music.

Middleton Tavern

Hardesty also popularized Middleton’s famous Oyster Shooter, to be enjoyed as part of the restaurant’s convivial bar scene. Brick walls, well-worn wooden floors and fireplaces on the first and second floors add to the restaurant’s historic appeal. The restaurant was the first in Annapolis to offer Sunday brunch. Its black bean soup, Chateau Briand and seafood dishes are first-rate. Everything about Middleton’s is casual until you climb the stairs to a pair of formal dining rooms decorated in period style and opened for overflow crowds or private parties. Prepare for crowds on fall weekends and arrive early for Sunday brunch.


Find a prime example of Georgian architecture and careful curating of its 1747 origins at the beautifully restored Reynolds Tavern (7 Church Circle) in the heart of Annapolis. Marilyn and Wes Burger, innkeepers since 2003, are usually on-site at this history-rich location, which includes two dining rooms, an inviting outdoor courtyard, the intimate 1747 Pub in the cellar and three upstairs guest rooms.

Reynolds Tavern

Records preserved by Farmers Bank and the Annapolis Library Association (20th century tenants of the building) show that the wooden floors, whitewashed plaster walls, fireplaces and ceilings date back to the mid-18th century. Reynolds Tavern is a true Annapolis treasure, the perfect place to enjoy its popular daily teas and lunches or dinner (Wed-Sun).

Proper British teas, featuring an extensive selection of specialty brews and tiered servers for the sweets and savories, are available daily from noon-5 pm. All pastries (including the fabulous fruit scones) are made in-house and the chef’s creations range from shrimp and cheddar grits with tomato-bacon jam to a creamy scallop risotto and bangers and mash. The kitchen, which also provides light fare for the Pub, is open daily 11 am-5 pm. Whenever you go, history will be waiting.


If you want a taste of history with your homemade popovers, the Treaty of Paris Restaurant downstairs at the Maryland Inn (11 Church Circle, with it's main entrance located on Main Street) will fill the bill. Named after the treaty that ended the War for Independence, was signed in Paris in 1783, and ratified by in 1784 by the United States Congress in the Maryland State House, the restaurant is a formal dining space with fireplaces at each end and an atmosphere that aims to preserve its roots.

Treaty of Paris

Breakfast, served daily from 7-11 am, is the restaurant’s strong point. Fancy choices include crepes overflowing with spinach, crab and ricotta cheese – napped with cheese sauce and partnered with sausage or hickory-smoked bacon; “Sea and Eggs”, featuring two soft shell crabs with a creamy crab and shrimp sauce paired with bacon and sausage and eggs; and “Eggs Chesapeake”, featuring a crab cake peeking out of poached eggs on an English muffin. Or just be happy to find a place that serves a “historic” breakfast of good old bacon and eggs.

Look around for antique mementos, have fun with the popovers that are a signature item – and come back later in the day for a libation in Maryland Inn’s historic Drummer’s Lot.

Note: Desperate for a Starbucks fix? Find one in the cellar of the Maryland Inn (16 Church Circle). Photos of such jazz greats as Ethel Ennis, Charlie Byrd and Monty Alexander are reminders of its glory days as a legendary jazz club.