Portsmouth Olde Towne Historic District

St. Paul's Catholic Church is a historic Roman Catholic church located in Portsmouth, Virginia, United States. It is a compact Gothic Revival style, cruciform plan church. It is constructed of load-bearing masonry walls clad in quarry-faced granite. The church was designed by John Peebles (1876-1934) in 1897, and dedicated in 1905. It is the fifth church on the site. Also on the property is a contributing rectory constructed in 1913.It was listed on the National Register of Historic Places in 2002. It is located in the Downtown Portsmouth Historic District. Yearly, the choir director and organ player, Nick Nespoli, who is also the chorus instructor of Western Branch High School, has his students from school perform at the church around Christmas. This concert is a free event, and the music performed ranges from secular to religious music. The main pieces performed are selections from the Messiah, by Handel, or the Gloria RV 589 by Vivaldi.

Monumental United Methodist Church, formerly known as Dinwiddie Street Methodist Church, is a historic Methodist church located in Portsmouth, Virginia. It is a five-bay brick and stucco, Victorian Gothic style church. It is features a 182 feet tall, two part central tower. The church was built between 1871 and 1876 on the foundations of an earlier 1831 building that had burned in 1864.The church was heavily damaged by fire on January 3, 2018. It was listed on the National Register of Historic Places in 2004. It is located in the Portsmouth Olde Towne Historic District.

United States Lightship 101, now known as Portsmouth as a museum ship, was first stationed at Cape Charles, Virginia. Today she is at the Portsmouth Naval Shipyard Museum in Portsmouth, Virginia. Portsmouth never had a lightship station; however, when the vessel was dry docked there as a museum, she took on the pseudonym Portsmouth. A National Historic Landmark, she is one of a small number of surviving lightships.

Portsmouth Courthouse, also known as Norfolk County Courthouse, is a historic courthouse building located at Portsmouth, Virginia, United States. It was built in 1846, and is a one-story with basement, Greek Revival style brick building. It measures 78 feet wide by 57 feet deep. The building is topped by a paneled parapet with Doric order entablature supported by plain Greek Doric pilasters. The building remained in use as a courthouse until 1960, when the county government moved to Great Bridge.It was listed on the National Register of Historic Places in 1970. It is located in the Downtown Portsmouth Historic District. The building now houses the Portsmouth Art & Cultural Center.

The Confederate Monument in Portsmouth, Virginia, was built between 1876 and 1881. It was listed on the National Register of Historic Places (NRHP) in 1997.The monument is a 35-foot obelisk of North Carolina granite. It is located at the town square of Portsmouth, on Court Street at the corner of High Street. Also facing on the town square are the Trinity Episcopal Church dating from 1828 and the Portsmouth Courthouse dating from 1846, which are also NRHP-listed.It was erected by the Ladies Memorial Aid Association of Portsmouth, Virginia, which was founded in 1866 with one purpose "being the erection of a monument to the Confederate dead of Portsmouth and Norfolk County." The design was by topographical engineer Charles E. Cassell.The cornerstone was laid in 1876.The monument's capstone was not placed until 1881, and the monument as a whole was not completed until 1893.The four cast white bronze figures that surround the obelisk, including their heads and facial features, are largely generic.: 536–537  The sailor figure, for example, also appears outside the G.A.R. Memorial Hall in Wabash, Indiana. The city of Portsmouth "gave 1,242 men to the Confederacy of whom 199 were killed or died; Norfolk County gave 1,018 men to the cause of whom 280 were killed or died; and the City of Norfolk gave 1,119 of whom 176 were killed or died."

Commodore Theatre is an historic movie theater located at Portsmouth, Virginia. It was built in 1945 in the Streamline Art Deco style, and originally sat 1,000 people. The theater closed in 1975 and sat empty until a change in ownership and extensive renovation beginning in 1987. It reopened two years later, and as of 2023 was in operation displaying first-run films accompanied by a full kitchen.

Trinity Episcopal Church is a historic Episcopal church located in Portsmouth, Virginia. It was built between 1828 and 1830, and is a stuccoed brick building. It has an attached bell tower. Also on the property is the contributing parish house, built in 1887. During the American Civil War, the church was used as a hospital.Rt.Rev. C. Charles Vaché, who served as its rector for 19 years before becoming the Bishop of Southern Virginia, wrote a history of the parish.It was listed on the National Register of Historic Places in 1973. It is located in the Downtown Portsmouth Historic District.

Downtown Portsmouth Historic District, also known as the High Street Corridor Historic District, is a national historic district located at Portsmouth, Virginia. It encompasses 229 contributing buildings, 1 contributing site, 4 contributing structures, and 1 contributing object in the central business district of Portsmouth. The district encompasses the original 1752 plan of the Town of Portsmouth and includes portions of expansions of the original boundaries dating to 1763 and 1909. It includes a variety of commercial, government, and institutional buildings, with most dating to the years around the turn of the 20th century. Notable buildings include the Captain Baird House, Vermillion Manor (1840), City Hall Building (1878), former United States Post Office (1907-1908), First Presbyterian Church (1877), First United Methodist Churches (1882), St. James Episcopal Church, Ebenezer Baptist Church, YMCA building, Tidewater Building, Southern Aid Building, Colony Theater, Lyric Theater, Blumberg's Department Store, Mutual Drug Company (1946), the New Kirn Building, and the Professional Building. Separately listed are the Commodore Theatre, Portsmouth Courthouse, Pythian Castle, St. Paul's Catholic Church, and Trinity Episcopal ChurchIt was listed on the National Register of Historic Places in 2004.

Kirill Ivanovich Denyakin (Russian: Кирилл Иванович Денякин) was a 26-year-old Kazakhstani national, who was fatally shot by a police officer in Portsmouth, Virginia, United States, on the evening of April 23, 2011. Later found to have been intoxicated but unarmed at the time of the shooting, Denyakin was shot by Officer Stephen Rankin of the Portsmouth Police Department, who was responding to a report of a burglary at the home where Denyakin was staying. According to Rankin and the Portsmouth Police, Denyakin had ignored Rankin's verbal orders and lunged at him aggressively just prior to the shooting, forcing Rankin to defend himself. Denyakin's family and friends have questioned this account of the incident. A grand jury declined to indict Rankin on criminal charges in February 2012, and the jury in a civil trial found him to be not culpable for Denyakin's death in March 2012.

The Children's Museum of Virginia is the largest children's museum in the state of Virginia. It is located in Olde Town Portsmouth at 221 High Street. The museum has a planetarium and two floors of exhibits. Its antique toy and model train collection is one of the largest on the East Coast. Highlights of the museum include a life-size tug boat and house, as well as a real Hampton Roads Transit bus, the cab of a real fire truck from the Portsmouth Fire Department, and a real motorcycle from the Portsmouth Police Department.

The Pythian Castle is a historic three-story brick-and-stone Knights of Pythias building located at 610-612 Court Street in Portsmouth, Virginia. Built between 1897 and 1898 for the Atlantic Lodge, Knights of Pythias, it was designed by architect Edward Overman in the Romanesque Revival style of architecture. Like many multistory urban fraternal buildings built in the late 19th and early 20th centuries, its street floor was rented out for retail and office spaces while the upper floors were reserved for lodge use. In 1908 a single-story brick-and-stone Romanesque Revival addition was built to the north of the original building. In 1979 the Pythian Castle was sold by the knights. On October 30, 1980, it was added to the National Register of Historic Places. Today the ground floor is a Mexican eatery.It is located in the Downtown Portsmouth Historic District.

Cedar Grove Cemetery is a historic public cemetery located at Portsmouth, Virginia. It was established by an act of the Virginia General Assembly in 1832. The cemetery contains more than 400 graves with monuments dating from the late 1700s to the present. Its memorial markers include small tablets, ledger stones, obelisks, columnar monuments and mausoleums. They include notable examples of Greek Revival, Late Victorian, and Exotic Revival funerary art.It was listed on the National Register of Historic Places in 1992.