Pleasant Valley, (Cooksville, Maryland)

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

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.

Hood's Mill is an unincorporated community located in Howard County and Carroll County in the state of Maryland in the United States of America. Hood's mill is community formed at the Benjamin Hood's Hood Haven on the Patapsco River. Later Hood's Mill was known as a stop along the B&O railroad with a shipping center run by the Hammond family.

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.

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.

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.

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.

South Branch Park is a historic industrial site located at Sykesville, Howard County, Maryland, United States. The site is the location of the James Sykes Mill to which Sykesville is named, an 1870 Stone House, as well as the 1917 B.F. Shriver Canning Factory and Howard Cotton Factory. James Skykes defended his homeland serving in the War of 1812.The Sykesville mill was constructed of granite with waterwheel power, and operated as the Mechant's Flour Mill. It burned once and was rebuilt by Skyes as a cotton mill. It was used by Governor Frank Brown as a storehouse in the late 1800s when the mill was out of service. A 1905 fire destroyed the mill, with $12,000 in damages paid to Brown in insurance.In 1996 Howard County purchased 7.6 acres of historic industrial land from Tisano Reality with State Open Space Funds for the creation of a South Branch Park. In 2011, Howard County leased the land back to the town of Sykesville for $817,583 and requested $617,000 from the town to help complete restoration of the buildings and site construction capital costs.In 2011 another $256,000 state grant was awarded to implement a park at the historic site including restoration of a caboose. Matching county funds were anticipated, but not provided. Updated plans included a skate park, parking lot, stormwater pond, and reroofing of the B.F Shriver Canning Company "Apple Butter Factory" is scheduled at an undetermined date for phase II. Phase III plans to restore the factory. On 6 September, County Executive Ken Ulman and candidate Courtney Watson opened phase I of the South Branch Park which included a new playground and the dismantling of a historic water tower as part of a series of pre-election groundbreakings for partially funded projects around the county including the Regional Transportation Agency of Central Maryland terminal. The $269,000 project was funded by Program Open Space.In response to local residents constructing their own skatepark features while waiting for promised improvements, Howard County conducted a Charrette in October 2014 to determine features to a skatepark to be implemented by California-based Spohn Ranch Skateparks.

Sykesville station is an historic railway station was built by the Baltimore and Ohio Railroad's Old Main Line in 1831, located in the town of Sykesville, Maryland in Howard County on 7618 West Main Street. Sykesville had two side platforms, two railroad tracks, and a station building. The station was closed in 1950 and the station building is now a restaurant.

The Sykesville Historic District encompasses the center of Sykesville, Maryland. Sykesville is a small incorporated town in the Patapsco River valley in southern Carroll County, Maryland, and is located on the old main line of the Baltimore and Ohio Railroad (B&O), one of the first railroad lines in the United States, that section dating from 1831. The B&O train station is included in the district, next to the river. It was designed by E. Francis Baldwin in the Queen Anne style and built in 1883. It is currently a restaurant having outdoor seating on the original platform (only goods trains now pass). Other historically significant buildings in the district were built between the 1850s and the 1920s.