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.
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.
- Caroline Culinary Arts offers cooking classes and full-service catering, and a culinary incubator. They are home to Shore Gourmet Denton Market, where you can shop for specialty food items grown and made on Maryland’s Eastern Shore
- 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.
Helpful Resources for your Visit
Other websites of interest:
- Caroline County Government
- Maryland Office of Tourism Development
- Caroline County Council of Arts
- Caroline County Recreation & Parks
- Caroline County & Historical Society
- Choptank River Heritage Center
- Caroline Summerfest
- Caroline County Public Library
- Stories of The Chesapeake Heritage Area
- Civil War Trails in Maryland
Download Our Brochures
Finding a Way to Freedom
The Underground Railroad in Caroline and Dorchester Counties in the 1850′s is a 105-mile Driving Tour which will guide you to exhibits, homes and home sites, meeting houses, mills and courthouses that illustrate the story of the Underground Railroad in Caroline and Dorchester Counties.
Caroline County Arts Trail
Discover the vibrant arts scene of Caroline County, Maryland! Explore our unique public art displays, interesting shops, and visionary galleries. Find inspiration in our thriving arts community. Take a class, meet an artist, tour a studio, or shop for one-of-a-kind works of art.
Stitching Stories of Freedom Byway Quilt Block Trail
The Byway Quilt Trail is a public art project that features 15 quilt block replicas located along the Harriet Tubman Underground Railroad Byway in Caroline County. Each quilt block was handpainted by a community member or organization and portrays a theme related to the Underground Railroad. Follow the trail of historic quilt block patterns to learn about freedom seekers and their quest for freedom.
Museum of Rural Life
Caroline County is one of only a handful of counties in the United States that existed for more than 300 years solely dependent on an agriculturally-based economy. The Museum of Rural Life offers visitors a rare glimpse into this world through historic dwellings. This brochure explains some of the Museum’s most notable exhibits, including some or all of four different historic residences.
Outstanding Dreams Alpaca Farm
24480 Pinetown Road, Preston
410-673-2002 | OutstandingDreamsFarm.com
Fall in love with the wonderful world of alpacas! Visitors are welcome at Outstanding Dreams Farm, where they offers tours and a gift shop featuring items crafted from alpaca fiber, including clothing, gifts, yarn & more. Please call ahead to schedule your tour.
Ridgely Historical Society & Railroad Memorial Park
Located in the heart of Ridgely, Maryland, Railroad Memorial Park serves as a community focal point and brings to life the rich history of “Dream City.” The park is home to Reading Caboose 92813 and the Telephone Exchange building, as well as numerous events throughout the year, including Ole’ Time Ridgely Days the first weekend in May.
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.