Developer Revives Bold $50B Proposal to Connect Long Island and Connecticut with 14-Mile Bridge

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Suspension bridge concept connecting Bridgeport, CT, to Long Island across Long Island Sound for Rockland County transit development.
A proposed bridge spans Long Island Sound, linking Bridgeport, Conn., to Long Island as part of a $50 billion infrastructure vision.

BRIDGEPORT, Conn. — A sweeping vision to link Bridgeport, Connecticut, to Long Island via a 14-mile bridge is gaining renewed attention, thanks to local developer Steve Shapiro. Reviving a century-old idea, Shapiro argues the bridge could slash travel time from three hours to just 20 minutes, while easing traffic congestion and unlocking massive economic growth.

The proposed span would connect I-95 in Bridgeport to the Sunken Meadow State Parkway on Long Island. It’s not just an ambitious transportation upgrade—it’s being pitched as a transformative investment in the region’s future.

“This is about more than infrastructure,” Shapiro said. “It’s about building for our future.”

Estimated at $50 billion, the project would be financed through federal funding and recouped via tolls. Shapiro insists it would not burden Connecticut or Long Island taxpayers.

The bridge, he says, would be a game-changer for the region’s economy. Reducing congestion on I-95, the most congested highway in the U.S., could have a direct impact on productivity and regional GDP. “When people sit in traffic instead of working, the economy suffers,” he noted.

Shapiro’s plan also features a train deck, promoting green travel. He estimates it would remove the equivalent of 250,000 cars from the road, significantly cutting CO₂ emissions. “It’s affordable, eco-friendly, and smart,” he said.

Despite the bold pitch, the idea isn’t without controversy. Concerns about environmental impact and noise echo the reasons why similar plans have failed in the past. In the 1960s, Robert Moses proposed a bridge between Rye and Oyster Bay. It collapsed under intense community opposition, federal restrictions, and environmental objections. Governor Nelson Rockefeller ultimately killed the project in 1973 after fierce backlash from residents and conservation groups.

Still, Shapiro believes his plan avoids past pitfalls. Unlike Moses’ proposal, this bridge would connect two urban areas with existing infrastructure. He says it’s not just feasible—it’s overdue.

Shapiro estimates the bridge could generate up to $10 billion annually in new revenue once operational. With the region grappling with a rising population and outdated transport systems, he believes this project offers a rare opportunity.

“In a state that starts with ‘Connect’ and a city called ‘Bridgeport,’ it just makes sense,” Shapiro said.

Local, state, and federal leaders have yet to formally weigh in, but if momentum builds, this long-dormant idea could leap from vision to reality.

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