A proposal to build a bridge linking Long Island to Connecticut is once again sparking conversation—and controversy—nearly a century after the idea first surfaced.

The latest plan, introduced by Connecticut developer Steve Shapiro, calls for a 14-mile span stretching across Long Island Sound from Bridgeport, Connecticut, to the Sunken Meadow Parkway on Long Island’s North Shore. If completed, the project would mark the first direct roadway connection between Long Island and New England.

Supporters say the bridge could transform regional travel, easing congestion and offering an alternative route for drivers who currently must pass through New York City to reach the mainland.

“We have such an opportunity in Connecticut and on Long Island to connect our two regions,” Shapiro said in a promotional video.

The proposed crossing would cost an estimated $50 billion to construct, with tolls projected at roughly $39 each way. Plans could also include a rail component to accommodate both passenger and freight service.

The idea of a cross-sound bridge is not new. Discussions date back to the 1930s, but repeated proposals over the decades have failed to gain enough political or public support to move forward.

At Sunken Meadow State Park, where the bridge could make landfall, residents and visitors expressed mixed reactions.

“I think it’s helpful with traffic—alleviating congestion trying to get to the city,” said Gus Hueber of East Northport.

Others worry about the environmental and cultural impact on Long Island’s character.

“It would destroy this area,” said Maureen Abbatecola of Kings Park. “It might make it easier for people to get on and off Long Island, but it’s also very special that this is an island—and that might take some of that away.”

Shapiro has suggested a potential compromise to address environmental concerns, including a hybrid design that would tunnel a portion of the route beneath the shoreline near the park.

“You could tunnel it under about a mile or two offshore and then go under the park,” he said.

In Connecticut, a bill that would authorize a feasibility study for the bridge was introduced in the state assembly but has not yet advanced out of committee. Despite that, Shapiro remains optimistic, emphasizing that cooperation between New York, Connecticut, and the federal government would be key to making the project a reality.

For now, the proposal remains in its early stages—but as it has for generations, the idea of bridging Long Island Sound continues to divide opinion on both sides of the water.