Hood's Mill, Maryland

Woodmont Academy was a private school in Howard County, Maryland, affiliated with the Legionaries of Christ, a Catholic religious institute.

Shipley's Adventure is a historic plantation home located in Cooksville and (Woodbine) Howard County, Maryland. The house is the homestead of George Shipley, and Catherine Ogg and was part of the 1260 acre "Shipley's Adventure" land grant patented on 7 April 1761. In 1790, "Shipley's Enlargement" was added to the estate. The house is built around a 1761 log cabin containing a loft which windows have been added. In 1972 a family room was added to the "telescoping" building. The estate has been subdivided down to 16.53 acres by the 1970s with the Perilla family converting the agricultural land for wine making.

The Red House Tavern is located in Cooksville in Howard County, Maryland, United States. It was situated midway along the Old Frederick Road between Baltimore and Frederick, used as a rest stop for travelers. The house is the birthplace of Thomas Cook born in 1768, who founded Cooksville in 1802.The 1+1⁄2-story-tall stone house was built in the 18th century when the region consisted mostly of slave-operated tobacco plantations. The building was built with a high pitched roof and dormers. The house was described by Ferdinand Baynard in his 1791 writings as a "rather poor" tavern, kept by a widow of "admirable reserve". George Washington was reported to have stayed at the inn during his travels along the main western road of the era. The original kitchen was located in the basement of the stone building with iron bars set to discourage looting. A log house is situated southwest of the building. A frame kitchen addition was later added to the rear of the building. In 1976, the property consisted of 125 acres (51 ha) owned by H.B.L. Properties (E. Brooklee). The property has since been subdivided into a series of pipe-stem residential lots, with the original parcel maintaining a large commercial construction operation on the property.

Located Cooksville near Sykesville in Howard County, Maryland, United States, Pleasant Valley, known as Lost by Neglect. The historic house is located on a portion of the 100-acre land grant named "Good Neighborhood" surveyed by Adam Shipley in 1742. In 1754, the section was part of a 103-acre land grant surveyed by Mordecai Selby Sr. called "Selby's Inheritance" and resurveyed as a 226-acre lot in 1775 as "Lost by Neglect". The original structure was built with stone construction in 1754. In 1859, a wooden addition was built by Henry Forsythe and given the name Pleasant Valley. In 1888 Henry Forsythe moved to the neighboring "Oaklands" plantation, leaving the estate in the hands of his heirs. Outbuilding include two barns, one of which was built with peg construction situated on land that has been subdivided from the estate. By 1976, the estate has been subdivided leaving only 14 acres of the original parcel remaining.

Gaither is an unincorporated community in Carroll County, Maryland, United States. It is located along Gaither Road, just north of the South Branch of the Patapsco River and the Old Main Line railroad line of CSX Transportation.

Roberts Inn, is a historic home and farm located at Cooksville, Howard County, Maryland. The complex consists of a 2+1⁄2-story stuccoed stone house with a reconstructed log wing built about 1808, and several 19th- to early-20th-century agricultural outbuildings, including a frame bank barn, a frame ground barn, a tile dairy, and a frame silo. The construction of the house coincided with the extension of the National Pike through the Cooksville area. Documentary and architectural evidence supports its use as a turnpike tavern from an early date. Tradition holds that Marquis de Lafayette breakfasted at Roberts Inn during his 1824 tour of America.It was listed on the National Register of Historic Places in 2006. It is located off of Route 144 off the intersection of Route 144 and Route 97.

Cooksville is an unincorporated community in Howard County, Maryland, United States. As of 2016, the population was 631. The town was founded by Thomas Cook in 1802. The crossroads town was anchored by the Joshua Roberts Tavern, where General Lafayette visited in 1824. The inn was destroyed by fire, rebuilt, and demolished a second time. Thomas Cook exchanged his stake in Cooksville with Thomas Beale Dorsey for the 231-acre Round About Hills slave plantation. A Post Office opened on the 4th of July 1851, the same year Howard County was formed from a portion of Anne Arundel County. Roberts Inn was listed on the National Register of Historic Places in 1973.On June 29, 1863, J. E. B. Stuart marched 5000 confederate soldiers through Cooksville en route to Westminster.

Hugg-Thomas Wildlife Management Area is a Wildlife Management Area in Howard County, Maryland, south of the town of Sykesville. The area comprises two parcels totaling 275 acres (111 ha). The Carroll County portion includes the estate of Admiral Jacob Hugg, including the ruins of the Hugg mansion.

Located Cooksville in Howard County, Maryland, United States, Poverty Discovered, "Summer Hill Farm" "Poverty Discovered" is named after the 1737 acre land tract Given to Joseph Hobbs by Lord Calvert in 1760. It was then owned by Captain Thomas Hobbs, who was involved in the burning of the Peggy Stewart. He willed the property to his son, Kentucky General Assemblyman Joseph Hobbs Jr. The slave farm was situated on the road to Ellicott's Mills from Hood's Mill. By 1783, "Poverty Discovered" was subdivided and consisted of 400 acres. On November 3, 1793, Henry Howard sold the Poverty Discovered estate of James Beached at public auction.The Poverty Discovered plantation house was built c. 1760. It is log construction with brick and stone construction additions with left-centered doors. Outbuildings include a log framed structure. In the 1930s a porch was enclosed for a kitchen. William J Bryson owned the house in the 1970s and substantial renovations occurred in 1989. The building is registered by the county as HO-117, with an abbreviated history.In 1966, the Rouse Company added "Poverty Discovered" to the list of local historical names to call their new land development project.The Property is now run as the "Summer Hill Farm" which raises thoroughbred horses for track uses or sale. Neighboring Greenway farms also resides on land once named "Poverty Discovered". In 2012, the resale of the adjacent Woodmont Academy sparked controversy as a high density use of the property next to the historic site.

Sarah Jane Powell Log Cabin, is a historic home located at Cooksville, Howard County, Maryland, United States. In 1850, Thomas Hood was one of three founding county commissioners of Howard County. In 1859 Thomas Hood built the log cabin on his property for his slave Sarah Jane Powell (born 1827) for her "unwavering fidelity and general moral worth as a servant". The cabin is a 3-bay-wide, 1+1⁄2-story-tall structure with a brick fireplace. Sarah Jane Powell married Alfred Dorsey, and had their first child in the cabin in 1865. In May 1869, the 1+1⁄4-acre property the cabin resided on named "Poverty Discovered" was deeded to Sarah Jane Dorsey. The cabin has been occupied by over seven generations of Dorseys, with a family graveyard located on the property. The property is just north of a former crossroads town named Inwood, and adjacent to a 30-acre parcel owned by the Board of Education in the 1970s, which has not been developed.

Mount Gregory United Methodist Church is a historically black United Methodist Church located at 2325 Roxbury Mills Road in Cooksville, Maryland. The building was constructed in 1898.

Sykesville is a small town in Carroll County, Maryland, United States. The town lies 20 miles (32 km) west of Baltimore and 40 miles (64 km) north of Washington D.C. The population was 4,436 at the 2010 census. BudgetTravel.com named Sykesville 'Coolest Small Town in America' in June 2016.