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Heritage Trails | Sites & Landmarks | Museums | UGRR | Genealogy & Historical Info
Federalsburg Heritage MuseumFederalsburg Transportation & Heritage Museum
The Federalsburg Area Heritage Museum is housed in the historic Covey and Williams garage building.  The restored structure features unique artifacts and exhibits of local heritage.
100 Covey Williams Alley, Federalsburg




Choptank River Heritage CenterChoptank River Heritage Center
The wharf site traces its origins to 1774. The museum which includes an old schooner and steamboat warehouse, offers educational programs on historic port towns, navigation, boatbuilding, river tours and other aspects of maritime life. The Center is completing an extensive inventory of maritime sites along the Choptank and Tuckahoe Rivers.
10215 River Landing Road, West Denton


Museum of Rural LifeMuseum of Rural Life
The Museum of Rural Life tells the stories of early Americans living in Caroline County’s agriculture-based economy. The museum exhibits includes the Taylor-Brown Dwelling, the Painter’s Range log cabin, and portions of the Chance’s Desire and Skillington’s Right properties.
16 N. Second Street, Denton



 Linchester MillLinchester Flouring Mill Complex
One of the last water-powered mills on the Eastern Shore, it ceased operating in 1979 when the mill pond dam broke after heavy rains. The structure has been described as a “treasure of America” because its original equipment reflects the long evolution of American milling. Of special interest is the Fitz water- wheel on the south (rear) side of the mill, and the Miller’s dwelling across the road.
3390 Linchester Mill Road, Preston 410-673-1910


Lily PadOne Room Schoolhouse/Woman’s Club – now Lily Pad Café
This Gothic style structure was built in 1883 as a primary school and was accepted onto the National Register of Historic Places in 1978. The school operated until 1925 and was purchased in 1926 by the Denton Community Club. Although several renovations have been made, much of the structure remains as originally built.
104 S. Second Street, Denton 410-479-0700



Ridgely Telephone MuseumRidgely Telephone Exchange Museum
In 1905 the Farmers and Merchants Telephone Company, created by entrepreneurs in Caroline County, erected the finest telephone system on the Eastern Shore, connecting all of the towns in the county, plus major towns in the Mid-Shore.  The C & P Telephone Company purchased the Farmers and Merchant system in 1911.  Telephone subscribers in Ridgely increased from 10 in 1905 to 120 in 1937.  C & P erected a new brick structure in the 1950s, setting in motion the odyssey of the Ridgely Telephone Exchange.
Railroad Avenue, Ridgely.
Open daily from 10:00 am – 5:00 pm. Closed December, January & February.


Tuckahoe Meeting HouseTuckahoe Meeting House – Privately owned
The meeting house was built in 1802 by members of the Society of Friends, who had been Nicholites, a sect that originated in Caroline County. The building was used as a house of worship and as a Friends School until 1897. The building was then rented by “Dunkards” for religious meetings for blind persons and as a school.
At Routes 404 & 328, West Denton



Webb-Fluharty Log Cabin
This rare dwelling built about 1852 by James H. Webb, a free black, probably survived because he salvaged ballast stones, left by vessels in the nearby river, and erected the cabin atop the stones. Webb lived in the small cabin with his wife and two children, whom he had purchased from a nearby slaveholder.
Off Route 16 on Grove Road, 2 miles on left side of road, near Preston

Williston Community Church
The Williston Community Church, built for the Congregationalists in about 1868, was most likely adapted from plans by Richard Upjohn, one of the most prominent architects of the mid-nineteenth century in America. The construction is called “board-and-batten” and is very similar to the construction style of the Williston Mill, one half mile south on Harmony Road. The style, popularized by Upjohn as a way of achieving a Gothic style without the expense of stonework, was known as “Carpenter Gothic.”
8270 Harmony Road/Route 16 between By-Pass Road and Williston Lane, Williston