Grace Episcopal Church (Hopkinsville, Kentucky)

Freeman Chapel C.M.E. Church is a historic Christian Methodist Episcopal church at 137 S. Virginia Street in Hopkinsville, Kentucky which was built during 1923–25. It was added to the National Register of Historic Places in 1983.It was deemed significant both for its history and its architecture. It is a two-story brick Classical Revival-style building on a tall basement foundation. It has arched clerestory windows.

The Hopkinsville Commercial Historic District of Hopkinsville, Kentucky, is a historic district listed on the National Register of Historic Places. The site was first inhabited by the Wood family of Jonesborough, Tennessee. They donated five of their 1,200 acres (4.9 km2) for the creation of a county seat, and in 1799 the site was platted and dubbed Christian Court House. Later in 1799 it was dubbed Elizabeth in honor of the Woods' eldest daughter, but due to the existence of Elizabethtown in Hardin County, in April 1804 the town was named in honor of General Samuel Hopkins.Places in the district that are separately on the National Register include the Confederate Memorial Fountain in Hopkinsville and the Hopkinsville L & N Railroad Depot. The fountain is now located by the Christian County Courthouse. The Depot brought many passengers to spend time in Hopkinsville, as it was the one place along the railroad between Evansville, Indiana and Nashville, Tennessee where one could consume alcoholic drinks.Other prominent buildings located in the district are the Pennyroyal Area Museum, the First Presbyterian Church, and the Old Fire House and Clock Tower. The Pennyroyal Area Museum, open since July 8, 1976, is in the historic old Hopkinsville post office, and is funded by the local government. The First Presbyterian Church was used as a hospital for General Nathan Bedford Forrest's men during the winter of 1861–1862; they were hospitalized due to a flu epidemic. The Old Fire House is currently the headquarters of the Christian County Historical Society.

The L & N Railroad Depot in the Hopkinsville Commercial Historic District of Hopkinsville, Kentucky is a historic railroad station on the National Register of Historic Places. It was built by the Louisville & Nashville Railroad in 1892.The year 1832 saw the first of many attempts to woo a railroad to Hopkinsville. This first attempt was to connect Hopkinsville to Eddyville, Kentucky. In 1868 Hopkinsville finally obtained a railroad station, operated by the Evansville, Henderson, & Nashville Railroad. The Louisville & Nashville Railroad acquired the railroad in 1879.The Hopkinsville depot is a single-story frame building with a slate roof. It has six rooms: a Ladies Waiting room (the room closest to the street), a General Waiting Room, a Colored Waiting Room, a baggage room (the furthest room from the street), a ticket office (the only room which connected to all three waiting rooms), and a ladies' restroom. Immediately outsides were warehouses for freight, usually tobacco.Its last long-distance train was the Louisville and Nashville's Georgian, last operating in 1968.During its operating years, the Hopkinsville depot was a popular layover spot for those traveling by train. It was the only Louisville & Nashville station between Evansville, Indiana and Nashville, Tennessee where it was legal to drink alcohol. Hopkinsville got the nickname "Hop town" due to train passengers asking the conductors when they would arrive at Hopkinsville, so they could "hop off and get a drink".The Hopkinsville L & N Railroad Depot was placed on the National Register of Historic Places on August 1, 1975. It is owned by the City of Hopkinsville and was occupied by the Pennyroyal Arts Council until 2019. That year the council moved out after a fire in an exterior wall and the building was still vacant as of January 2023. The depot's future was uncertain as it requires an estimated $2M USD in structural repairs and those costs are in competition with other city funding priorities.CSX, which bought out the Louisville & Nashville, still run freight trains on the tracks next to the depot.

The East 7th Street Historic District in Hopkinsville, Kentucky is a 12 acres (4.9 ha) historic district which was listed on the National Register of Historic Places in 1983. It included 17 contributing buildings, and is roughly E. 7th St. from Campbell to Belmont Streets.It includes Virginia Park, which is separately listed on the National Register, and up to 1912 was the site of an unpretentious frame home (c.1845) of John C. Latham, a Hopkinsville businessman and philanthropist.It includes Greek Revival, Queen Anne, and Prairie School architecture.

Bethel College was a Baptist-affiliated college in Kentucky founded in 1854 and closed in 1964. Throughout most of its history, the Hopkinsville campus was a women's college while the Russellville campus was a men's college.

J. B. Knight House is listed on the National Register of Historic Places and located in the city of Hopkinsville, Kentucky.

Attucks High School is a former school in Hopkinsville, Kentucky, built in 1916. It was Hopkinsville's first public school for black students and was converted to an integrated middle school in 1967, the Attucks Middle School or simply Attucks School, before being shut down in 1988. It was listed on the National Register of Historic Places in 2013. It is at 712 1st Street. The school was built partially from brick reclaimed from a former school, the Clay Street School. It was designed by architect John T. Waller and was built by the Forbes Manufacturing Company in a somewhat Italian Renaissance style, at a cost of $17,640. The listing includes two contributing buildings.

Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. The population at the 2020 census was 31,180.

Hopkinsville Community College (HCC) is a public community college in Hopkinsville, Kentucky. It is one of 16 two-year, open-admissions colleges of the Kentucky Community and Technical College System (KCTCS). Founded in 1965, HCC maintains a main campus in Hopkinsville and an off-site campus on the Fort Campbell Army base. HCC is accredited by the Southern Association of Colleges and Schools (SACS). It offers Associate in Science and Associate in Applied Science degrees.

The E. H. Higgins House, at 1530 E. 7th St. in Hopkinsville, Kentucky, is an American Four Square house built in 1920. It was listed on the National Register of Historic Places in 1984.It was deemed to be a "fine example of the American Four-square style". It is a two-and-a-half-story house built upon a stone foundation. It has a hipped roof with a central dormer and it has a one-story porte-cochere.

University Heights Academy (University Heights or UHA) is an independent, college preparatory school for students in pre-kindergarten through 12th grade located in Hopkinsville, Kentucky. The school was founded in 1973. As of April 2023, K-12 enrollment is 417. The school also includes a day care center, an all-weather track, a softball field, a baseball field, a soccer field, walking trails, a pond and stream, an astronomy pad, and an activity building/gymnasium. When the school first opened, its mascot was initially the Blue Devil; in 1976, the student body voted to change this to the Blazer. UHA has long had a strong athletics tradition: In 1992, the boys' basketball took home the KHSAA state trophy. It also offered one of the first school soccer teams in western Kentucky and the first in Christian County. According to Hoptown Chronicle, at its opening, the school introduced itself to the Hopkinsville community by publishing the note below:An Open Letter to the Community: We are proud to be able to offer the children of our community a new dimension in education. University Heights Academy takes for its motto the traditions of classical education. The Academy is an expression of the desires of the citizens of our community educate their children so that religion, moral discipline and academic achievement shall continue to be their birthright. In the years to come our children will discover not only the beauty of learning but will learn about themselves as unique individuals. The Academy’s future is as bright as their hopes.More than 1,000 students graduated from UHA during its first 50 years. Successful alumni include The Black Crowes drummer Steve Gorman, NBA basketball player Greg Buckner, Hoptown Chronicle founder Jennifer Brown, and Tell Me What You See author Terena Elizabeth Bell.

Hopkinsville High School is a four-year public high school located in Hopkinsville, Kentucky, with over 1,000 students. It is operated by the Christian County Public Schools school district.