In the 1950s city officials believed that New Haven needed a highway link to the towns of the Lower Naugatuck Valley. The Oak Street Connector, a freeway extending from I-95 northwest, and also known as Route 34, was thought to be the answer—but the project was an undisputed failure. To clear the way for a never-completed segment of highway that severed Yale’s medical campus and the nearby Hill neighborhood from the downtown, 881 families were displaced and 350 buildings razed.

Now, more than 50 years after it was built, New Haven Mayor John DeStefano Jr. has proposed a plan to remove the connector, restore the street grid, and reknit the city’s fabric.

The plan, which DeStefano announced at an April 20 press conference, would nearly double the size of the city’s central business district; create 4.5 million square feet of new commercial, institutional, retail, and residential space; produce 12,000 permanent jobs; and generate more than $100 million annually in tax revenue.

A joint effort of the city, Yale-New Haven Hospital, the School of Medicine, and the Economic Development Corporation of New Haven, the plan is by all measures ambitious. A $5 million federal grant secured by U.S. Representative Rosa DeLauro has funded the project so far. The cost of the plan’s infrastructure, estimated at $45 million, will be financed through federal, state, and private funding. Engineering work for this phase of the project has already begun, but it is expected to take years to complete.

A private-sector project will jump-start the initiative. Winstanley Enterprises, a property development firm based in Concord, Mass., is ready to break ground on a 300,000-square-foot office and laboratory “sister building” to 300 George Street between the Air Rights Garage and College Street in the Route 34 right-of-way as soon as the state land and air rights are transferred. Developer Carter Winstanley, owner of 300 George, envisions closing Route 34’s Exit 3, with several lanes of traffic rerouted. An existing entrance to the Air Rights Garage would remain.

“We are just ecstatic with the vision that the downtown will extend to the medical center and that we will be a part of it,” said Dean Robert J. Alpern, M.D., Ensign Professor of Medicine. Alpern said the plan addresses two important issues: the medical school’s disconnection from “such a vibrant downtown” and its ability to grow. The only limitation on growth in research and clinical care is space, he said.

“We’ve been somewhat landlocked. But now, with plans for the conversion of the downtown, this will create opportunities for a lot of new research buildings,” Alpern said.

The plan is “going to be a positive circumstance for the university,” said Bruce D. Alexander, J.D., Yale’s vice president for New Haven and state affairs and campus development. “We’ve been working hard whenever we had the opportunity to reconnect the central campus and the medical campus. This will be a very significant step forward.”

DeStefano said the plan is meant to “create a footprint for what happens to New Haven over the next 15 years.”