Chesapeake Bay

Maryland State House

Annapolis

We took a short trip around Chesapeake Bay in April 2025.  First stop was Annapolis, which we loved!  The downtown is historic and very well preserved, most buildings dating from the eighteenth and early nineteenth century.  Make sure to stop at the informative visitor center at 26 West Street (and have a drink at the Rams Head Tavern across the street!)

Cecil Calvert, Second Lord Baltimore requested a royal grant from King Charles I in 1632, for the northern Chesapeake, which was carved out of the existing Virginia colony and named in honor of Queen Henrietta Maria.  There are still buildings surviving in Annapolis and the eastern shore from this early colonial period.  

The Maryland State House in Annapolis is the oldest capitol building in America, built in 1772 and still used by the state legislature.  The self-guided tour is a great way to experience the history of the building.  The Treaty of Paris (1783) ending the Revolutionary War was signed here.  In December 1783, General George Washington resigned his commission from the Continental Army in the Maryland State House, and returned to civilian life as America's Cincinnatus.  The Maryland State House hosted the Annapolis Convention of 1784 which called for a Constitutional Convention, and acted as the Capitol of the United States from November 1783 until August 1784.  

The US Naval Academy was very impressive, and seeing the midshipmen was inspiring.  The 90 minute guided tour was the best way to see the Yard.  The USNA Museum is very well curated, providing a great history of the Navy. The Chapel is modeled after Napoleon's Tomb in Paris, and John Paul Jones is buried in the crypt. 

USNA Chapel

Chapel Nave

Across from the USNA is St John's College, founded as King Williams' School in 1696.  It is the third-oldest college in America after Harvard and William and Mary (Yes, same King William).  Their interdisciplinary degree is focused on reading and discussing a curriculum 200 classics.  HERE is the Undergraduate reading list.  

St John's College

The William Paca House (1763) and Gardens, home to a signatory of the Declaration of Independence, has an excellent docent tour, and is an outstanding view into early colonial life.  

Wm Paca House Gardens

Wm Paca House Gardens

Maryland Avenue is a quiet street with shops and the excellent Old Fox Books & Coffeehouse.  Nearby is the Galway Pub which is famous for their Irish whiskey selection 

The Federal House across from the Annapolis market has great French onion soup and crab soup.  The nearby Middleton Tavern is an historic inn and a great place for drinks.

Historic Reynolds Tavern dates from 1747; we had a forgettable dinner in the Pub.

Iron Rooster has great breakfasts, with morning and afternoon happy hours! 

Choptank has great breakfast and views of Spa Creek, also known as Ego Alley for the expensive yachts docked there.  

We had an excellent dinner at Preserve, the smoked fish dip was particularly good.

The Annapolis Waterfront Hotel has great rooms in a great location.  

St Michaels

Located on the eastern shore of the Chesapeake Bay, tiny St Michaels is a very cute harbor town, and Talbot Street is lined with restaurants and shops.  Founded in 1677, St Michaels flourished as a shipbuilding a trading center in colonial times.  The St Michaels Harbour Inn had a large suite at a great price (off season).  We did not choose our restaurants wisely, so I would not recommend Harrison's Harbor Lights or Foxy's Harbor Grille; however, JoJo's Ice Cream was great!  

St Michaels Harbor

St Michaels Harbor

Talbot Street

Baltimore

We spent a day in Baltimore, exploring some neighborhoods.  Inner Harbor is really pretty, but we were surprised by the lack of restaurants/bars (compared to a few years ago).  Fells Point is beautiful and historic, with list of things to do. We visited the downtown area around the Washington Monument along Charles Street.  The Peabody Library of Johns Hopkins University is incredible, one of the most beautiful libraries in America.  Finally, we had an excellent dinner overlooking Inner Harbor at The Rusty Scupper; best crabcake we've had!

Peabody Library

View from Rusty Scupper

Washington Mon.