It carries US 13, which saves motorists roughly 95 miles (153 km) and 1+1⁄2 hours on trips between Hampton Roads and the Delaware Valley and points north compared with other routes through the Washington–Baltimore Metropolitan Area.

After sailing across the Atlantic Ocean from England, they reached the New World at the southern edge of the mouth of what is now known as the Chesapeake Bay.

As the entire colony grew, the bay was a formidable transportation obstacle for exchanges with the Virginia mainland on the Western Shore.

Consequently, little industrial base grew there, with the oceanfront peninsula staying predominantly rural with small towns and villages oriented towards life on the waters, and most residents made their living by farming and working as watermen, both on the bay (locally known as the "bay side") and in the Atlantic Ocean ("sea side").

Despite an expanded fleet of large and modern ships by the VFC in the 1940s and early 1950s which were eventually capable of as many as 90 one-way trips each day, the crossing suffered delays due to heavy traffic and inclement weather.

It still serves transit needs, but the number of pleasure trip passengers increased as the coastal beach resorts developed and grew crowded with vacationers in the next decades, partly due to the improved swifter transportation with highway, bridge, and tunnel access in the region of three states.

Eventually, the shortest route, extending between the Eastern Shore and a point in Princess Anne County at Chesapeake Beach (east of Little Creek, west of Lynnhaven Inlet), was selected.

[6] To address these concerns, the engineers recommended a series of bridges and tunnels known as a bridge–tunnel, similar in design to the Hampton Roads Bridge–Tunnel, which had been completed in 1957, but on a considerably longer and larger facility.

The tunnel portions, anchored by four artificial islands of approximately five acres (2.0 ha) each, would be extended under the two main shipping channels.

[6] In mid-1960, the Chesapeake Bay Ferry Commission sold $200 million in toll revenue bonds (equivalent to $1.58 billion in 2023 dollars) to private investors, and the proceeds were used to finance the construction of the bridge–tunnel.

During the Ash Wednesday Storm of 1962, much of the partially completed work and a major piece of custom-built equipment, a pile driver barge called "The Big D", were destroyed.

In April 1964, 42 months after construction began, the Chesapeake Bay Bridge–Tunnel opened to traffic and the ferry service discontinued.

The Ferry Commission and transportation district it oversees, created in 1954, were later renamed for the revised mission of building and operating the Chesapeake Bay Bridge–Tunnel.

Eastern Shore native, businessman, and civic leader Lucius J. Kellam Jr. (1911–1995) was the original commission's first chairman.

In a commentary at the time of his death in 1995, the Norfolk-based Virginian-Pilot newspaper recalled that Kellam had been involved in bringing the multimillion-dollar bridge–tunnel project from dream to reality.

According to the newspaper article, "there were not-unfounded fears that (1) storm-driven seas and drifting or off-course vessels could damage, if not destroy, the span and (2) traffic might not be sufficient to service the entire debt in an orderly way.

Sure enough, bridge portions of the crossing have occasionally been damaged by vessels, and there was a long period when holders of the riskiest bonds received no interest on their investment."

An icon of eastern Virginia politics, Kellam remained chairman and champion of the CBBT throughout the hard times, and the bondholders were eventually paid as toll revenues caught up with expenses.

The 1995–1999 project increased the capacity of the above-water portion of the facility to four lanes, added wider shoulders for the new southbound portion, facilitated needed repairs, and provided protection against a total closure should a trestle be struck by a ship or otherwise damaged (which had occurred twice in the past); partially for this reason, the parallel trestles are not located immediately adjacent to each other, reducing the chance that both would be damaged during a single incident.

In 2013, the CBBT Commission approved a project to construct a second tunnel under the Thimble Shoal channel for an estimated cost of $756 million.

The machine, nicknamed Chessie in a naming contest, was capable of moving forward through soil at 2.4 in (61 mm) per minute, or about 50 ft (15 m) per day.

After boring, the machine will also be adding the circular concrete segments which will be delivered into the tunnel via mine cars one at a time.

As of 2024, the toll for cars (without trailers) traveling along the CBBT is $16 for off-peak or $21 for peak times (Friday through Sunday from May 15 to September 15).

[25] As part of the Thimble Shoal Channel Tunnel twinning, the building housing the restaurant and gift shop closed and access to the pier was prohibited starting at the end of September 2017.

The columns that support the CBBT's trestles—called piles—would stretch for about 100 miles (160 km) if placed end-to-end, roughly the distance between New York City and Philadelphia.

Despite an extensive search, he remained missing until April 2021, when his body washed up over 100 mi (160 km) south at Cape Hatteras National Seashore between Salvo and Avon.