Preserving Caroline's History & Culture

The Society has worked to preserve over fifty historic buildings. We also preserve and safeguard sacred sites, precious artifacts, and shared stories.

The Society is almost certainly the most active historical society in rural America in terms of the number of buildings being preserved. Located from Goldsboro to Choptank Village, our projects are found throughout the county.  All preserved buildings must have a specific future use. Most will become the centerpiece or parts of multi-building and multi-site educational “interpretive centers” to tell unique stories that highlight the national historical signifcance of Caroline County as well as the qualities that make us so exceptional.

For example, Caroline’s resilience produced an extraordinarily unique 350+ year history of commercial agriculture as our only major industry; our service to country led to Caroline’s unmatched record of residents fighting in every major battle save one in American history; and our moral courage gave Caroline the best Underground Railroad history in rural America.

Plain Dealing (Caroline Poor House) “Salvaged”

Plain Dealing (Caroline Poor House) “Salvaged”

Interior and exterior walls had badly cracked from major structural problems, numerous fire-burned holes punctured the roof, and mold turned the interior ceilings black. After initial spending by the Society for stabilization and documentation, extensive meetings with...

read more
Castle Hall Saved

Castle Hall Saved

Castle Hall in Goldsboro (c. 1781) was dark, vacant, neglected, and deteriorated, with ongoing vandalism that included broken doors, graffiti-sprayed walls and hundreds of smashed window panes, once-proud Castle Hall with the finest colonial woodwork in Caroline sat...

read more
Circa 1829 Slave Dwelling Discovered

Circa 1829 Slave Dwelling Discovered

The Society was offered an “old shed used as a meat house and granary”, but what we discovered had a lot more history: A one-room dwelling that our architectural consultant said was originally a slave dwelling, our dendrochronologist dated to 1829, and court records...

read more

Hear All of Our Stories

Capt. Quentin R. Walsh, USCG – WWII Hero

Capt. Quentin R. Walsh, USCG, led a small group of US sailors and soldiers to secure the port of Cherbourg and help ensure success of the Normandy Invasion on D-Day.  Read more about Capt. Walsh's heroism.  Walsh settled in Denton after retiring from the Coast...

Passing of CCHS President, JOK Walsh

We mourn the loss of our long-time President, JOK Walsh.  JAMES OWEN KNOTTS (JOK) WALSH of Denton, MD passed away on Thursday, July 13, 2023, at Maryland MICU Hospital in Baltimore. The former Attorney, President of Caroline County Historical Society, Economic...

Boonsboro School

Boonsboro School

Other Names: School No. 4 (1875), School No. 1 (1896) Earliest Documented: 1875 Latest Documented: 1896 Description Listed as School No. 4 in Denton Journal 1877 and on 1875 Isler map adjacent to (NW of) “Colored Church” at Boonsboro crossroads. The geographic...

Knott’s Mill

Knott’s Mill

Until recently, Knotts Mill in Tuckahoe Neck rivaled Wye Mill as the oldest continually operated grist mill in Maryland.  Located just a half mile from the wharf at Sloop Landing on the Tuckahoe, it was perhaps better positioned to rush flour and corn meal to feed Washington’s army during the Revolution.

In June 1781, while Washington and Cornwallis were moving their armies toward Yorktown, American Colonel Henry Hollingsworth reported to Maryland Governor Thomas Lee that 600 bushels of State wheat were stored at Seth’s Mill (earlier name of Knott’s Mill).

Chilton’s Mill

History and Location of Chilton SawmillOther Names: None Years: 1810 - 1875 Structure Exists?  No Historic Site Location Precision:  50 metersThe following text is extracted from John F. McGrain, The Molinography of Maryland, Expanded, 2007 Edition for Posting Online...

Dickinson’s Mill Rediscovered with Lidar

Ruins of a mill dam survived on Fowling Creek Branch on Wiltshire Manor and have been identified as either a Blades Mill or Dickinsons Mill by Mrs. Clara Mitchell of Preston, October 17, 1967. This land at Grove near Preston had been owned by Henry Dickinson and several generations of Isaiah Blades heirs. Read more…