Red House Tavern

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.

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.

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

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.

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.

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.

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.

Inwood is an unincorporated community in Howard County, Maryland, United States. The crossroads settlement was settled around Woodlawn, home of Dr. Edwin Warfield, which has been removed for the Gary J. Arthur Community Center and Cooksville Library. The town once featured a general store, blacksmith shop and residential homes. The neighborhood postal service is now consolidated around Cooksville. Inwood is a very small historic town located between Cooksville and Glenwood.

Bushy Park is a historic slave plantation located at Glenwood, Howard County, Maryland, United States. It is located on a 3,940 acre land patent named "Ridgley's Great Park".Bushy park is known as the home of Charles Alexander Warfield. Warfield married Elizabeth Ridgley of Laurel in 1771 and settled in a log home at "Bushy Park". The same year he started construction on his slave plantation manor home. On 19 October 1774, Warfield and his neighbors travelled to Annapolis and burned the Peggy Stewart in retaliation to sanctions on Americans following the Boston Tea Party. Paintings of the incident are displayed in the State House at Annapolis and the Court House at Baltimore. In 1866, Charles D. Warfeild sold the 270-acre and 160-acre Bushy Park tracts containing an eight-room stone and frame house, including two tenant houses, blacksmith shop, 250-tree apple orchard and 73-tree peach orchard. The property later was owned by the "Hammond" family of the Major Charles family line. The manor stood for over 150 years, burned in 1933, and was demolished in 1947. A new house was built over the original foundation. In 1978, the property was purchased by the Clevenger family and had been subdivided down to 342 acres, but was still actively farmed. In 1983, it had been subdivided down to a 190-acre parcel named "Bushy Park Farm" and sold again. A portion of the original estate became the Carr's Mill Landfill, which became a site of hazardous waste dumping by Western Electric in the 1970s. Howard County spent millions of dollars to cap the landfill and dispose of hazardous materials after contamination of groundwater on the site. Warfield is buried at Bushy Park. The walled cemetery remains, but the majority of the 1300-acre farm has been redeveloped as the Western Regional Park, operated by Howard County.

Glenwood Middle School is located in the western portion of Howard County, Maryland. It is built on land settled in the early 18th century by the Ridgley and Warfield families forming large slave plantations such as "Bushy Park", "Longwood", "Ellerslie" and others. The design was put together by Lorenz Murray the firm of Johannes and Murray. The plans included an air-conditioned combined "cafetorium" and library. An even more aggressive consolidation of cafeteria, auditorium and gymnasium "Cafetorianasium" was also proposed. The School Board insisted on deciding the color of the brick. In March 1966, the board asked the County Commissioners to sell bonds to fund $1,270,000 for a new middle school and to purchase school sites for the new Rouse development of Columbia. On June 28, 1966 the company of Charles. J. Cirelli, Inc. won the bid to build the school for $1,159,000. The Contract was approved in the same session where Robert H. Kittleman was protesting school board actions against teachers as a representative of the National Association for the Advancement of Colored People. Cirelli built several schools for Howard County and was the employer of Maryland Governor Marvin Mandel after his pardon from mail fraud and racketeering charges. Dr. DiVirgilio recommended additional changes in the design totaling $11,239.69 before completion and J. Norman Otto Co., Inc won the $19,783.00 bid on cafeteria furniture. Water was supplied by two wells and a new requirement for sprinkler systems added another $53,000 to the cost. Ba-Mor supplied carpeting. Cost overruns started with the removal of additional unexpected rock. Jack Kussmau was selected as the first principal and Donald Bell as vice principal in 1967.By 1996, parents petitioned the school board about lack of maintenance and exclusion from capital budgets for upgrades. Parents listed problems with water on gym floors and in walls, overcrowding and ventilation issues. In 2000, students staged a sit-in to protest the dismissal of a teacher.In winter of 2016, the school was closed for a week and relocated at Bushy Park Elementary School, Dayton Oaks Elementary School, and Marriotts Ridge High School due an underground powerline short that caused a fire. In addition, from 2014 to 2016, Glenwood Middle School was a center of controversy due to a mold problem found in the portable classrooms.