Plan Your Visit

Enjoy Caroline’s wealth of unique heritage experiences, nature preserves, winding waterways, gently curving countryside, epicurean escapes, small town charm and one-of-a-kind group excursions.

Caroline County Trip Ideas


Caroline County is rich in Underground Railroad history.

  • Harriet Tubman freed herself from slavery in Caroline County.
  • The Linchester Mill was a part of the east/west secret network used to assist freedom seekers.
  • Ben Ross, Harriet Tubman’s father, was leader of the west side of the secret network.
  • Moses Viney: 23 years a slave, 69 years a New York entrepreneur
  • James H. Webb was a free man who purchased his wife and children out of slavery. His log cabin was recently restored and is now open to visitors.
  • Anna Murray Douglass, from Denton, was an entrepreneur, fundraiser, wife of Frederick Douglass.
  • Sidney Still made a “Sophie’s Choice” decision for freedom.
  • Peter Still was kidnapped for 36 years.
  • William Still: Author of the Underground Railroad
  • Pay Cannon was the evil face of the slave trade.
  • Richard Poer was a free black kidnapped, taken out of state and rescued. He became a future education supporter of the Freedman’s Schools.


History comes alive in Caroline County. Possible topics of interest include:

  • Indian Paths – Indian pathways heading north, south, east and west converge in Greensboro.
  • Three Centuries At Sea: The Sailing Vessels Of Caroline County – Clipper ships, Schooners, Brigantine, Brig and Sloops were all made in Greensboro.
  • Mason-Dixon Line – Discover the Crown-stones of the Mason-Dixon Line.
  • The Golden Age of Steamboats – Explore the Choptank River Heritage Center Steamboat Museum.
  • Civil War Trails – Discover stories of the Civil War.
  • One-of-a-Kind Museums – Explore the Museum of Rural Life, Federalsburg Heritage Museum, Greensboro Museum, Ridgely Telephone Exchange Building, Tuckahoe Meeting House and more.
  • Sophie Kerr House – Famed author Sophie Kerr resided in Caroline County.


Delight your senses with an epicurean experience in Caroline County.

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