Thomas Jefferson visited Annapolis, Maryland three times:

• May 1766. Jefferson was on his way to Philadelphia and New York to inoculate himself from smallpox. He wrote to his friend John Page from Annapolis discussing his trip.[1]
• June 1775.  On this trip, Jefferson was on his way to Philadelphia to attend sessions of the Continental Congress.
• December 1783 until May 11, 1784. Jefferson served as a delegate to Congress during this period.  (Annapolis was the U.S. capital from November 1783 to August 1784.)

Further Sources

• Dumbauld, Edward.  Thomas Jefferson, American Tourist.  Norman, Okla.: University of Oklahoma Press, 1946. 
• MB.  Contains records of Jefferson's purchases and movements while in Annapolis.

Footnotes

• 1. PTJ, 1:18-20.