The Oak Street Connector, a mark of New Haven’s urbanist past that has sliced downtown New Haven in two, is not a popular roadway.

University President Richard Levin called it a “big canyon through the center of the city.”

[ydn-legacy-photo-inline id=”7968″ ]

[ydn-legacy-photo-inline id=”7969″ ]

Mayor John DeStefano Jr. called it an “inefficient” use of space.

School of Management professor Douglas Rae called it a “mistake.”

When it was first opened about six decades ago, the roadway, also known as Route 34 Connector, decimated the Oak Street neighborhood. But by early 2011, at least some of that mile-long highway could all but disappear. Over the next decade or so, city officials hope the highway will close and become four development sites and a boulevard at the heart of the city.

By next year, the city intends to start closing two of the Connector’s exits to make way for a mixed-use building, called 100 College St., that could allow for more biotech industries to come and bring more than 900 permanent jobs to New Haven.

“It knits the city back together,” DeStefano said in an interview last week. “It’s like having a cut on your body and healing it back together.”

Yet the highway has become part of the city’s landscape, as well as an often-used transportation option for commuters into the city, and some residents worry about what its destruction could mean for their travel plans.


The Oak Street neighborhood in the 1950s was crowded with tenements, and the sidewalks were strewn with litter. It was primarily inhabited by Jewish, Irish and Italian immigrants. It was a thriving area reminiscent of New York’s Lower East Side in the early half of the 20th century.

It was also a slum.

In his third run for mayor, in 1953 (the first two runs were unsuccessful), Richard Lee vowed to clear the slums in the city, focusing on Oak Street, said Rae, who served as chief administrative officer in 1990 and 1991 and authored a book about New Haven’s history called “City: Urbanism and its End.” The Connector, a part of Lee’s urbanist redevelopment plan, gave the mayor a way to get rid of the neighborhood.

Traffic was terrible in the city before Lee started his plans, Rae said. To accommodate drivers and create a city “safe for the automobile,” Lee created several roadways, including the Connector and Interstates 91 and 95, said Gaddis Smith ’54 GRD ’61, the Yale historian and Larned professor emeritus of history.

But Mary Florenzano, whose family has lived in Wooster Square for four generations, said the highways destroyed her “self-contained” Italian neighborhood. And the Route 34 Connector, which runs from Interstates 91 and 95 to the Air Rights Garage spanning York Street, forced families in the Oak Street neighborhood out of their homes.

Lee did not finish his Route 34 Connector plans in part because the city did not have enough money, Rae said in an e-mail message. (“Thank God [the city] didn’t do it,” Smith said.)

The Route 34 Connector, which was meant to connect to main highways to the west of the city, was left the way it stands now: a monster that DeStefano said “consumed open space.”


Today, the area between the Cooperative Arts and Humanities High School and the Yale School of Medicine campus is barren. There is not much noise save for the sounds of cars driving on the Connector. The streets here are not busy with pedestrians.

For several decades, city and state officials have attempted to continue plans of extending the highway; in some plans they also considered bringing biotech industries to the area. DeStefano first thought of closing it about five or six years ago, when the city acquired land west of the Air Rights Garage, which spans York Street along North and South Frontage roads. The area was home to growing biotech companies and an expanding Yale University, and the lots on nearby Temple Street and in downtown had all but been filled.

Now, city officials are calling the 400,000-square-foot 100 College St. the first phase of the transformation of the area — the Downtown Crossing Project. New Haven Economic Development Administrator Kelly Murphy said the city will start developing the other three sites as officials receive proposals.

“[100 College St.] hopefully will allow us to continue to meet the needs of the University, the hospital and Connecticut’s biotechnology companies,” said Carter Winstanley of Winstanley Enterprises LLC, the building’s developer, which owns more than one million square feet of property in the city.

Winstanley said that when his company purchased the nearby 300 George St., which currently houses companies such as Achillion Pharmaceuticals Inc., he did not intend to only work with biotech industries. But, he added, he “saw strength” in the city’s work in the field.

Mary Kay Fenton, vice president and chief financial officer of Achillion, said biotech industries are a “win for everybody” in the city and the state, and that building new locations that can house these industries give companies like hers flexibility in case they grow in size.

The city’s plan to close exits 2 and 3 along the roadway and prepare for the 100 College St. development will cost about $30 to $40 million, Murphy said. The city obtained $5 million in federal money in 2005, Murphy said, adding that the city hopes to attract some project money from state and federal governments. Murphy said the building, which will be financed by Winstanley Enterprises, is projected to cost between $120 and $160 million and will be completed within the next three years.

DeStefano said the city will find “most every reasonable means we can find to support the project,” but he did not specify how the city would pay for the project if it does not receive state or federal funding. He ruled out raising taxes for the project.


While standing outside their workplace, 300 George St., Diane Giordano and Dawn Fusco, both employed by the Yale Medical Group, lamented the future loss of the Route 34 Connector.

“They can’t do that!” Giordano said. “That would stop the traffic from coming to the hospital!”

“It’ll take us another 25 minutes to get to work,” Fusco added. “They can’t!”

In response, City Hall spokeswoman Jessica Mayorga said in an e-mail message that the Downtown Crossing Project would “improve the street grid and not create new obstacles.”

But although Rae said DeStefano’s efforts to resurrect New Haven’s “urban fabric” should be praised, he added that there was a benefit to having the Route 34 Connector.

Michael Piscitelli, director of New Haven’s department of transportation, traffic and parking, said his department is working to make “modifications” to North and South Frontage roads to make way for 100 College St.

To accommodate drivers during construction, the city will remove the College Street overpass and create a structure that will allow cars to enter the Air Rights Garage, according to an application the city completed in September for federal funding. And to create a direct route to the School Medicine, the city will extend Lafayette Boulevard into the Hill neighborhood within the year, city officials said. DeStefano added that once the Connector is closed, travelers headed toward Yale’s central campus could still use I-95 and I-91.

In interviews over the last two weeks, Yale officials said they are willing to see the highway die if it causes the area’s rebirth. Levin said the project would make the trek from central campus to the hospital more “pleasant” on foot.

“Anything that makes the connection stronger between the medical center and the main campus would be a real plus for us,” he said. “It would improve the quality of life for people on the School of Medicine campus.”

School of Medicine Dean Robert Alpern said in an e-mail last Monday that his school wants to be part of downtown. And if all goes as the city plans, the death of the connector will create a new community — a neighborhood not of immigrants, but of businessmen, doctors and scientists.