Downtown Tunnel

Seaboard Coastline Building, also known as Old City Hall, is a historic train station located at Portsmouth, Virginia. The original section was built in 1894-1895 by the Seaboard Air Line Railroad. It is a five-story brick and concrete structure, with the top two floors added in 1914. The front facade features a distinctive half-round or semicylindrical profile intended to recall the imagery of the streamlined locomotives of the late-19th century. The building served as the northern terminus and office headquarters of the Seaboard Air Line until 1958.

The Portsmouth Naval Shipyard Museum and the associated Lightship Museum are located on the downtown Portsmouth, Virginia, United States waterfront. The museum covers the 250+ year relationship with the shipyard - America's oldest and largest naval shipyard located on the Portsmouth Waterfront. The city and the shipyard have been intertwined since the founding of the Gosport Shipyard in 1767, which was later renamed Norfolk Navy Yard and finally Norfolk Naval Shipyard. This rich history is told through exhibits, hands-on programs and special events. The Lightship Portsmouth is a museum ship that is part of the Portsmouth Naval Shipyard Museum. Built in 1915 and began service as part of the U.S. Lighthouse Service in 1916. In 1964, the lightship was retired to Portsmouth, Virginia. In 1989, the Lightship Portsmouth was designated a National Historic Landmark. Now a museum, the ship's quarters are fitted out realistically and filled with artifacts, uniforms, photographs, models, and more.

The Atlantic Union Bank Pavilion (formerly the nTelos Pavilion and Union Bank & Trust Pavilion) is an outdoor amphitheater in Portsmouth, Virginia, United States. The venue produces and presents a broad spectrum of concerts and events connects audiences to the inspirational power of music and helps new generations of listeners discover the wonder of music and live performance. The venue invites audiences and artists to celebrate the joy of live music, the power of community, and the magic of the Pavilion. The covered outdoor Pavilion is located on the banks of the Elizabeth River in downtown Portsmouth, Virginia and provides one of the best live entertainment experiences in the Hampton Roads area. It has a capacity of 6,500 people and is located directly across the Elizabeth River from downtown Norfolk.

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.

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.

Quarters A, B, and C, Norfolk Naval Shipyard are three historic officer's quarters located at the Norfolk Naval Shipyard in Portsmouth, Virginia. They were built about 1837, and are three Greek Revival style brick dwellings. Quarters A is the most formal and sits on a high basement and covered by a hipped roof with interior end chimneys. It features a central entry with Doric order pilasters, plain full entablature and blocking course. Its design is taken directly from Plate 28 of Asher Benjamin's The Practical House Carpenter (1830). Quarters B and C also sit on a high basement and covered by a hipped roof with interior end chimneys.Quarters A, the residence of the shipyard's commanders, was extensively damaged by fire on 12 August 2014.The residences were listed on the National Register of Historic Places in 1974.

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."

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.

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.

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.

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.

The Interstate 264 Berkley Bridge is a double-leaf bascule bridge that crosses the Eastern Branch of the Elizabeth River in Norfolk, Virginia, United States. It carries Interstate 264 (I-264), U.S. Route 460 Alternate (US 460 Alt.), and State Route 337 (SR 337) across the river, connecting the Berkley neighborhood south of the river with downtown Norfolk to the north. The toll-free facility is one of only a small number of movable bridges on the Interstate Highway System, and is the first of two in the Hampton Roads region, predating the High Rise Bridge. It is named for the former Town of Berkley that is now a part of the City of Norfolk.