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

FREEDOM SEEKERS & THE UNDERGROUND RAILROAD

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.

HERITAGE EXPERIENCES

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.

EPICUREAN DELIGHTS

Delight your senses with an epicurean experience in Caroline County.

  • Chesapeake Culinary Center is a nonprofit that offers a culinary incubator, job-training for the students in the culinary field, cooking classes and full-service catering.
  • Steve Konopelski, Pâtissier was a final competitor on the Food Network’s Holiday Baking Championship creates fabulous desserts and runs a waterfront B&B, Turnbridge Point.
  • Faulkner Branch Cidery & Distilling Company offers a homegrown experience where visitors can pick apples and peaches and taste the only locally brewed hard cider on the Eastern Shore.
  • River Run Cruises offers crab feasts and catered picnics on the scenic Choptank River.
  • Harvest Ridge Winery is a family farm winery nestled in the beautiful countryside.

Download Our Brochures

Request a Printed Brochure

Use the form below to request a guide or brochure from our offices. Please allow up to 2 weeks for your brochure(s) to reach you at the address provided. If you have any questions, please contact our office at (410) 479-0655.

  • This field is for validation purposes and should be left unchanged.