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Attractions

One of Caroline County’s biggest attractions lies in its rich heritage. History buffs are welcome to take a step back in time and experience a host of significant historic sites located throughout the region. More than a dozen Maryland Historic Markers can be found throughout the communities of Caroline County. What’s more, the county itself is home to six sites on the Maryland Civil War Trail, including Greensboro, Denton Wharf, the Caroline County Courthouse and the Nanticoke River. Caroline County also sits along the Harriet Tubman Underground Railroad Scenic Byway. Important sites discovered on this byway include Poplar Neck, the Leverton House, Denton’s Courthouse Square and Hillsboro.

Housed within a historic schooner and steamboat warehouse at Joppa Steamboat Wharf in West Denton, the Choptank River Heritage Center (CRHC) is dedicated to preserving and interpreting the significant history of the Great Choptank River and its relation to the agricultural and cultural development of the Eastern Shore region. Several exhibits, informational publications and research and educational opportunities can be discovered through CRHC.

Take a glimpse into the life of rural Caroline County, a region that is only one of a few counties in the nation that has existed for more than 300 years on a strictly agricultural-based economy, at the Museum of Rural Life in Denton. Popular highlights of the museum include a display of all or portions of four historic homes: Painter’s Range, Chance’s Desire, Skillington’s Right and the Taylor-Brown House.

Caroline County is more than just history, though—it’s also a hub for vibrant culture and exciting entertainment. A notable event held in Downtown Denton and Daniel Crouse Memorial Park is the Caroline Summerfest, a free, two-day family event featuring more than 100 diverse musicians and performers on four stages. Rock, country, blues, jazz and bluegrass music is complemented by talented magicians, jugglers, acrobats, dancers and more.

The Caroline County Council of Arts is an integral organization in the promotion and enhancement of the area’s cultural and educational community. Through the Council, residents and visitors can access an assortment of programs, classes and exhibits representing county culture and artists. The Councils’ Performing Arts Series brings in a variety of great entertainment to Caroline County. Through a number of various venues, guests can enjoy musical performances, stand-up comedy, dance troupes, circus acts and more. Held on the second story of the Caroline County Public Library in Denton, the 2nd Story Live! Concert Series is another event that brings in a wealth of nationally known performers.

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