Caroline County has many small towns with plenty of charm, hospitality and friendly faces.
Our quaint communities, rich in history and traditions, are linked by beautiful rural landscapes that you can drive or cycle along. Slow down and relax…enjoy the sights, the countryside, general stores, home-style cooking, antiques, unique gifts, soap box derbies, parades, street festivals, fireworks, fresh produce, and good old-fashioned ice cream cones.
Named after wealthy landowner, Dr. G.W. Goldsborough, the town’s earliest industry was beaver pelt trading with Native Americans. This was a lucrative business since four major Indian paths on the Chesapeake Peninsula converged here. With Oak Hickory and Oak Gum forests, abundant grain fields, spawning fish, edible plants, freshwater streams and fur-bearing animals Goldsboro grew into an important crossroads town. Today it remains one of the small charming villages that dot Caroline County’s scenic landscape.
A small village midway between Goldsboro and Marydel in northern Caroline County, Henderson was originally known as Melville’s Crossroads. The community developed around a stagecoach stop and a post office during the mid-19th century. With the advent of the railroad in 1868, the stagecoach service ended and the post office moved to the east side of town near the railroad where this quiet village was renamed Henderson. Caroline’s relaxing rural byways wind through many hospitable hamlets like this one.
Chronicled in Frederick Douglass’ famous 1845 autobiography, this community evolved as a tobacco-trading center on Tuckahoe Creek. Hillsboro was the setting for several important events in Douglass’ life including the permanent separation of his family among slaveholders. Hillsboro is a great place to launch a kayak or canoe, and has a soft public landing where paddlers can access Tuckahoe Creek.
Straddling the famous Mason-Dixon at the northern end of Caroline County, Marydel’s name is derived from its Maryland and Delaware roots. Visitors interested in history can view a crown stone of the Mason-Dixon Line, named after Charles Mason and Jeremiah Dixon who were hired to do the land survey. Although often referred to as the dividing line between the north and south, the Mason-Dixon Line resulted from a property dispute between the Penn and the Calvert families.
Because of its many free black households and sympathetic Irish immigrants, Templeville was once known as a safe haven for Underground Railroad escapees. On July 3, 1863, native son Sergeant William Poor of Templeville fought alongside 300 Caroline soldiers in the Union Army’s First Eastern Shore Regiment at Culp’s Hill at the Battle of Gettysburg. The Confederate soldiers included William Hardcastle, a descendent of Thomas Hardcastle of “Castle Hall” near Goldsboro.