Littleton Dennis Teackle, as did his father, took up a career in the trans-Atlantic trade, but his success was often undermined by the economic and political turbulence of the times. Despite the instability of the early 19th century, he became a successful merchant/planter, entrepreneur, banker, a member of the Maryland House of Delegates, and a strong advocate of a national banking system and currency as well as an advocate for a public school system.. His wife, Elizabeth Upshur, worked constantly at Teackletonia raising their daughter and managing the town estate with a score of servants. Her life, good and bad, her multi-faceted personality as well as her many talents and philosophies, are reflected in a large archive of letters she wrote to her husband, sister and daughter over the course of forty years. Her last years of residence were mostly in Washington, D.C. and Baltimore when her husband served in the Maryland House of Delegates. Her letters written during her years of residency in Washington reflect her's and her husband's close association with Congressional leaders active during the presidency of Andrew Jackson.

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