Named for Connecticut's famed Charter Oak, the original crossing opened as a toll bridge in the early 1940s, allowing through traffic to pass south of downtown Hartford.

[4] On December 4, 1941, disaster struck, when a 222 feet (70 m) section of the Charter Oak Bridge fell into the Connecticut River during construction.

Sixteen men fell to their deaths in the icy river, and 606 tons of steel, including a 176-ton derrick, plummeted into the water.

This included the Merritt Parkway, the Berlin Turnpike, and the Charter Oak Bridge, forming at the time Connecticut's most advanced, prominent highway.

[6] As traffic increased and the planned beltways (I-291 and I-491) were reduced in scope or cancelled entirely, the state paid particular attention to the overworked I-84/I-91 interchange and surrounding highways.

After considering alternatives such as widening or adding a parallel span, the state decided to build a new bridge immediately to the south, and dismantle the old one.

The Charter Oak Landing park was created on the footprint of the original bridge along the west bank of the Connecticut River.

On June 9, 2015, Governor Dannel Malloy announced a five-year, $200 million construction project to rebuild the interchange between US-5/CT-15 and I-91 at the west end of the bridge.