Oscar F. Smith High School

Chesapeake Regional Medical Center (CRMC) is a hospital accredited by the Joint Commission with an advanced certification as a primary stroke center.

Oak Grove United Methodist Church is located in Chesapeake, Virginia, and is known as "the mother of all Methodist congregations in Hampton Roads". It has helped found four other Methodist churches in the area: Community United Methodist, Great Bridge United Methodist, Messiah United Methodist, and Oaklette United Methodist It is located on the corner of North Battlefield and Great Bridge boulevards, and was the fourth Methodist church established in the Northampton County. The church's history dates back to the 1700s, and since then the church has established a wide variety of ministries and has been declared a historical structure. The church follows Methodism, a movement started by John Wesley in an effort to reform the Church of England from within.

Chesapeake Arboretum (48 acres) is a non-profit arboretum located at 624 Oak Grove Road, Chesapeake, Virginia. It is open daily without charge. The arboretum was established in 1996, and currently consists of a mature hardwood forest with good trail system, farmhouse, and theme and demonstration gardens. The Chesapeake Arboretum trail system is approximately 45 acres and is some 3.5 miles (5.6 km) in total length. A perennial stream, Starr Run, runs through the trail system and is crossed by 11 bridges.

Greenbrier Christian Academy (GCA) is a private Christian school located in the Greenbrier section of Chesapeake, Virginia. It was founded in 1983.

The Great Bridge Bridge is a double-leaf rolling bascule drawbridge that carries Battlefield Blvd (State Route 168 Business) across the Atlantic Intracoastal Waterway in Chesapeake, Virginia. It was constructed in 2004 by the Army Corps of Engineers and operated by the City of Chesapeake. It has a mean daily traffic of 35,000 vehicles. The current bridge cost $46 million. In September 2018 a lightning strike disable the bridge's electronics, requiring manual operation. Normally the bridge opens automatically, on the hour, from 6 am to 7 pm. Vessels can request an opening from 7 pm to 6 am.

The Battle of Great Bridge was fought December 9, 1775, in the area of Great Bridge, Virginia, early in the American Revolutionary War. The victory by colonial Virginia militia forces led to the departure of Royal Governor Lord Dunmore and any remaining vestiges of British power over the Colony of Virginia during the early days of the conflict. Following increasing political and military tensions in early 1775, both Dunmore and colonial rebel leaders recruited troops and engaged in a struggle for available military supplies. The struggle eventually focused on Norfolk, where Dunmore had taken refuge aboard a Royal Navy vessel. Dunmore's forces had fortified one side of a critical river crossing south of Norfolk at Great Bridge, while rebel forces had occupied the other side. In an attempt to break up the rebel gathering, Dunmore ordered an attack across the bridge, which was decisively repulsed. Colonel William Woodford, the Virginia militia commander at the battle, described it as "a second Bunker's Hill affair".Shortly thereafter, Norfolk, at the time a Loyalist center, was abandoned by Dunmore and the Tories, who fled to navy ships in the harbor. Rebel-occupied Norfolk was destroyed on January 1, 1776 in an action begun by Dunmore and completed by rebel forces.

Great Bridge is a community located in the independent city of Chesapeake in the U.S. state of Virginia. Its name is derived from the American Revolutionary War Battle of Great Bridge, which took place on December 9, 1775, and resulted in the final removal of British government from the Colony and Dominion of Virginia. The main branch of the Chesapeake Public Library named the Central Library, which itself is located in Great Bridge, displays a 12-pound cannonball, labeled as having been fired at the Battle of Great Bridge. The written histories of the battle are specific in stating that there were only two cannon at the battle, both British "four pounders." Though the battles of Lexington and Concord took place months earlier, and are historically more memorable, the Battle of Great Bridge can be seen as the first strategically important colonial victory over the British, forcing Lord Dunmore's 200 redcoats to evacuate Fort Murray and withdraw to Norfolk. The city hall as well as other major municipal buildings for Chesapeake lie within Great Bridge. Great Bridge was essentially a small town or crossroads until the late 1980s and 1990s, when it experienced significant growth. It contains large residential areas as well as many large shopping centers. Also, Great Bridge was the home of professional baseball players, Michael Cuddyer, David Wright, B.J. Upton, and Justin Upton. Former Virginia Tech, Denver Broncos, and Cleveland Browns defensive lineman Carlton Powell also hails from Great Bridge. Lawrence Johnson, the 2000 Summer Olympics pole vault silver medalist, is also from Great Bridge. Other local notable celebrities include Larry Bergman who in the 1956 Olympics in Melbourne, Australia won a gold medal in fencing and Thompson Mann, who won a gold medal for swimming in the 1964 Summer Olympics in Tokyo, Japan.

On November 22, 2022, Andre Marcus Bing killed six co-workers and injured four others before killing himself, in retaliation for perceived workplace harassment at the Walmart Supercenter where he worked as a night-supervisor in Chesapeake, Virginia, United States. Bing's suicide note cited concern he was being "led by Satan" and asking forgiveness - while also mentioning cancer treatments and loneliness.

The Veterans Bridge is a fixed span concrete bridge that spans the Southern Branch of the Elizabeth River in the Deep Creek neighborhood of Chesapeake in southeastern Virginia, USA. The bridge, which partially opened in 2014, currently carries two lanes of U.S. Route 17 (US 17; Dominion Blvd) on each direction across its northbound and southbound spans. The corridor frequently acts as a bypass route for congested I-64 High Rise Bridge traffic. It replaces the much shorter and smaller Dominion Boulevard Steel Bridge, which because of its 11-foot underwater clearance opened on average of 16 times per day.Tolling began on the route on February 9, 2017. Most cars, SUVs and passenger trucks that use the bridge and utilize an E-ZPass transponder will only pay $1 to cross. Larger vehicles, such as transit busses and semi-trailer trucks, will face an E-ZPass toll ranging from $1.50 to $2.50, depending on its classification. However, those same vehicles crossing without a transponder will still pay their respective base toll, but will also incur a $2 processing fee in addition to the original toll.The toll is expected to increase by approximately 5 percent each year through 2035.

Dominion Boulevard Steel Bridge (known locally as simply the Steel Bridge) was a double-leaf bascule, two-lane drawbridge which spanned the Southern Branch Elizabeth River in the City of Chesapeake in South Hampton Roads in southeastern Virginia. Built in 1962 and operated by the City of Chesapeake, it carried U.S. Route 17 (US 17) which is Dominion Boulevard (formerly numbered as State Route 104). The corridor frequently acts as a bypass route for congested I-64 High Rise Bridge traffic. Because of the low water clearance, bridge openings were commonplace for the bridge, with an average of 16 lifts per day. Combined with an average daily traffic count of 33,000, it frequently became a choke point for commuters who lived in the Deep Creek part of the city, with a failing level of service on the entire stretch according to a during a 2006 traffic plan by the HRPTO.In January 2013, Chesapeake Public Works began construction on a $345 million fixed-bridge replacement project called the Veterans Bridge, which was completed in late 2017. It expanded Dominion Blvd. from two to four lanes from the intersection of Cedar Road & Moses Grady Trail to the interchange of Great Bridge Blvd. The Veterans Bridge is tolled, which started at the rate of $1 in 2017. This project is also a part of the planning for the future Interstate 87 that will connect the Raleigh-Durham Metro area to the Hampton Roads region.After the first span of the Veterans Bridge opened in December 2014, the Steel Bridge was shut down and demolished.

Chesapeake is an independent city in Virginia, United States. At the 2020 census, the population was 249,422, making it the second-most populous city in Virginia, the tenth largest in the Mid-Atlantic, and the 90th-most populous city in the United States.Chesapeake is included in the Hampton Roads metropolitan area. One of the cities in the South Hampton Roads, Chesapeake was organized in 1963 by voter referendums approving the political consolidation of the city of South Norfolk with the remnants of the former Norfolk County, which dated to 1691. (Much of the territory of the county had been annexed by other cities.) Chesapeake is the second-largest city by land area in the Commonwealth of Virginia, and the 17th-largest in the United States. Chesapeake is a diverse city in which a few urban areas are located; it also has many square miles of protected farmland, forests, and wetlands, including a substantial portion of the Great Dismal Swamp National Wildlife Refuge. Extending from the rural border with North Carolina to the harbor area of Hampton Roads adjacent to the cities of Norfolk, Portsmouth, Suffolk, and Virginia Beach, Chesapeake is located on the Atlantic Intracoastal Waterway. It has miles of waterfront industrial, commercial and residential property. In 2011, Chesapeake was named the 21st best city in the United States by Bloomberg Businessweek. Chesapeake is home to the international headquarters of Dollar Tree.

The High Rise Bridge is a four-lane, bascule drawbridge that Interstate 64 (I-64) uses to cross the Southern Branch of the Elizabeth River. The twin spans of concrete and steel were completed in 1972, and are operated by VDOT. Currently, the High Rise Bridge is the only highway-grade toll-free crossing of the Southern Branch Elizabeth River, since the Downtown and Midtown Tunnel began tolling in 2014. Other non-interstate alternate routes include the Gilmerton Bridge on U.S. Route 13 (US 13; Military Highway), as well as the tolled Jordan Bridge in Portsmouth. Because of the high impact a bridge opening has on traffic, the bridge only opens on a 24-hour advanced notice unless the scheduled lift time is during the bridge's restricted hours of 6–9 am and 3–6 pm, when a three-day notice is required. The current reconstruction project intends to produce a fixed bridge with 100 feet (30 m) clearance, expected to significantly reduce traffic delays associated with bridge lifts.