End of the road

On a gray Thursday last November, a group of Yale students huddled on the corner of York Street and North Frontage Road, standing underneath the massive Air Rights Garage that straddles downtown New Haven and the city’s medical district. Two students, members of EnviroAdvocates, a politically-oriented project group that operates within the Yale Student Environmental Coalition, delivered a joint speech that called upon the City of New Haven to prioritize cyclists, pedestrians, and public transportation as it reconsiders infrastructure and redesigns roadways in the coming years. The weather was not ideal for an outdoor press conference. A persistent drizzle that postponed the event days prior had returned to push those in attendance under the oblong shadow of the parking structure, somewhat removing them from view. The timing, however, was on their side.

A week earlier, on Nov. 10, the Board of Aldermen had passed a resolution urging that equal weight be given to pedestrian, cyclist, vehicular, and mass transit accessibility and safety. The resolution did not carry the force of law, but there was symbolic heft behind its ratification. In tandem with the press conference, the resolution demonstrated the growing focus on city planning as one of the most significant transportation projects of the last half-century unfolds in the Elm City.


People rarely get riled up over traffic for more than 30 minutes a day, which is why the four-hour Board of Aldermen meeting on Sept. 28 was so remarkable. The discussion centered around modifications to the proposed design of the “Downtown Crossing” project along Route 34, a 1.1-mile highway that sprouts from the junction of Interstate 95 and Interstate 91. Also known as the Oak Street Connector (and officially as the Richard C. Lee Highway), the limited-access highway comprises six lanes—three eastbound and three westbound—and supports upwards of 75,000 vehicles daily. When the 32 million dollar Downtown Crossing project is completed, it will support zero.

In 2010, the Downtown Crossing proposal was effectively green-lighted when the federal government awarded the project 16 million dollars through the TIGER II grant program. Broadly speaking, Downtown Crossing will convert Route 34 from a depressed highway into urban boulevards at grade level, rehabilitate local street connections along the north/south axis, and greatly enhance pedestrian and bicycle options. On top of all that, the elimination of the highway will free a swath of new land for development.

The major elements of the first phase of the Downtown Crossing project are no longer up for debate. When Ward 10 alderman Justin Elicker, FES ’10 SOM ’10, introduced legislation in July that called for revisions to the 2010 design, he had no intention of derailing the project. “The goal of the resolution,” he said, “was making the project more neighborhood and community friendly.” At the four-hour September meeting, Elicker, whose carrot-colored hair frames his slender face and a constellation of freckles,  brandished a tape measure to show just how far pedestrians would have to walk to cross the street under the terms of the current plan. The intermittently contentious meeting ended in a stalemate, and a revised version of Elicker’s own legislation was passed in the Nov. 10 do-over.

Largely as a result of public pressure, the city retuned the design, adding measures to calm traffic and promote walking, such as raised crosswalks and pedestrian islands. Mike Piscitelli, the deputy economic development administrator and a primary point person for the Downtown Crossing project, reflected on the high levels of community involvement at public meetings. “It’s a testament to our public process that there are so many people engaged in this project,” he said.

It’s also an indicator of what’s at stake. Over the summer, public hearings confronted the redevelopment in excruciating detail. Not only were the number of lanes at the proposed urban boulevards’ widest points debated, but so was the width of the lanes themselves. By November, the proposal had been altered to show that lanes would be 10 feet wide, instead of 11 feet. The level of precision in which every aspect of the Downtown Crossing is being discussed reveals just how badly the city and its citizens want to get this right.

When the price tag of a first phase exceeds 30 million dollars, the expectations for any project run high. But for Route 34, these expectations are coupled with the specter of failure. “There’s a lot of excitement for the potential of the project, but also some amount of healthy fear about messing it up for a second time,” said Sarah Eidelson, JE ’12, the Ward 1 alderwoman and a member of the city’s Development Commission. The original Route 34 highway—which the Downtown Crossing will bury alive and crisscross with urban streets and new developments—required the razing of a neighborhood to build. Nearly 900 families and 350 businesses were displaced to make room for its construction. The six-lane artery, ironically named the Oak Street Connector, split New Haven in half along its waistline. And then it was never completed. In fact, the highway abruptly ends, just a mile after it begins, where the student press conference was held: the Air Rights Garage.


In 1958, the Saturday Evening Post ran a story with the subtitle, “Do old cities have to die? Consider how the young mayor of New Haven is bulldozing his ‘blight-ridden’ town out of a stagnant past into a handsome new future.” The mayor was Richard C. Lee, and his aggressive urban renewal policies received praise throughout the piece.

By the 1950s, New Haven, like many American cities with deep manufacturing roots, was showing signs of decline. Nowhere was this more evident than in the city center, where business struggled and neighborhoods spoiled into slums. Industry was leaving cities across the country, and wealthier people were caravanning with it to the suburbs. But New Haven had a plan—through intensive urban renewal, the city was going to keep its downtown vibrant. The Housing Acts of 1949 and 1954 opened the federal floodgates for urban renewal funding, and by the 1960s, no city had received as much money per capita for redevelopment initiatives as New Haven had. (By 1967, the city had received approximately 790 dollars per person for urban renewal projects. Newark, NJ, which had the second highest per capita rate, had received just 286 dollars
per person.)

The Oak Street Connector, completed in 1959, was a signature project of New Haven’s urban renewal efforts. Frank Chapman, ARC ’59, who worked for the city from 1963-68 before retiring as the deputy director of city planning, said that the primary goal of the highway was to revitalize the city center. Sitting with his wife at the kitchen table in their house on Edwards Street, Chapman, an affable man with an irrepressible twinkle in his smile, told me that “the idea was to make the access to downtown New Haven so good that it would pre-empt suburban development.”

To make room for the Oak Street Connector, the city decided to raze the Oak Street Neighborhood, an enclave—and slum—mainly inhabited by Italians and Eastern European Jews. At the time, the demolition of the neighborhood seemed to generate surprisingly little controversy. Douglas Rae, the Richard Ely Professor of Political Science and Management, told me that Mayor Lee practiced a particularly hardy brand of environmental determinism—an idea that at its most basic equates dirty neighborhoods with dirty people. At hearings on the acquisition of the Oak Street neighborhood for public development, city officials captivated citizens with accounts of the slum’s horrors: Crimes, fires, and prostitution existed there in record levels, they claimed. According to the article in the Saturday Evening Post, “even the 10,000 rats infesting Oak Street were photographed and publicized” as the land was being cleared. Rae suggested that one of the reasons for the Oak Street Connector’s six lanes was that a large highway would uproot more of the slum. “Making it wide allowed for a larger swath of housing to be taken down,” he said.

Yet while the city succeeded in razing the neighborhood, the Lee administration never completed the Oak Street Connector. Instead of extending the highway west to a major boulevard or freeway, the Oak Street Connector stopped where the Air Rights Garage now stands. The prevailing belief is that the city ran out of money in the middle of the project, but Rae and Chapman are reluctant to jump to that conclusion. “The Lee Administration wasn’t crushed by the fact that it didn’t continue [west] to the wetlands,” Rae said. Political pressure to complete the highway waned as the federal contribution relative to city funding diminished, and as Yale expressed new interest in developing the land adjacent to the highway. “Yale wanted the land to build on, which they did,” said Chapman. His wife, Alison, suddenly chimed in: “Route 34 died a political death!”


The result was a stunted stretch of road that bisected the city but didn’t provide any substantial increase in accessibility. Where an arm was supposed to be built, the city managed only a thumb. Because of this, traffic worsened in downtown New Haven, particularly around Yale. Cars that stream off of I-91 and I-95 and onto Route 34 are forced to exit the highway east of York Street, which leads to significant traffic along it and nearby streets during working hours. “The cars on York Street shouldn’t be there,” Chapman insists. “This should be a quiet, two-lane street.”

Instead, York and nearby roads are forced to absorb the traffic that a completed Route 34 would accommodate. The heavy automobile traffic in the downtown district has led to a strange blossoming of quasi-suburban developments. Reaching for a map, Chapman pointed to an image of a Walgreens on the corner of York and North Frontage, across from where the student press conference was held. The building, a plain, one-story box, is moated by a ground-level parking lot. “This site should have a building with four floors of offices, and residences on top,” he says.

At one time, New Haven’s downtown was home to the kinds of buildings and stores more typical of an active commercial center. Perhaps none was as iconic as the Edward Malley Company—otherwise known as Malley’s—a department store that first opened its doors to New Haveners in 1852. By 1899, the store, located directly across from the New Haven Green at 65 Chapel St., was nine stories tall. The department store, constructed in the Beaux-Arts style and home to both the first elevator and escalator in the state, was a New Haven landmark. Malley’s, along with other department stores like Gamble-Desmond and Shartenberg-Robinson, brought people in droves to New Haven’s downtown. In her 2001 book Going Shopping, Ann Satterthwaite, a city planner in Washington, D.C., wrote that the “downtown department store embodied urban excitement.”

Yet even Malley’s was not impervious to the effects of urban decline and the unintended consequences of urban renewal. As part of the Church Street Project, Malley’s was relocated in 1962 to 2 Church St., just off of the newly-minted Oak Street Connector. By 1982, the store had gone out of business. I met with Aldy Edwards, YC ’59, whose father, Richard H. Edwards, Jr., joined Malley’s in August 1953 as its Vice President and General Manager. Looking out over downtown New Haven from the top floor of the Omni Hotel, Edwards pointed to where Malley’s had been before and after the Church Street Project. As we talked over coffee, he recalled the reasons for Malley’s ultimate demise.

Macy’s, positioned in a more convenient location, became a major competitor, while Malley’s struggled to draw foot-traffic to its site along the Oak Street Connector. But while cars could access it as they exited the Connector, the unsolved murder of Concetta “Penney” Serra, who was stabbed to death in the Temple Street Garage in 1973, caused many shoppers to keep on driving, according to Edwards.

And then there was the Oak Street Connector itself, simultaneously too short to serve as an additional artery for eastbound commuters and too wide to allow convenient crossing for northbound shoppers, especially pedestrians. Chapman echoed many of Edwards’ sentiments. “The Chapel Square Mall—to which Malley’s was connected—died, in part, because it did not have access from all directions to all of its trade area,” he said. The aborted Oak Street Connector, which severed the connection between downtown New Haven and the medical district and Hill neighborhoods, had failed to save the Elm City. “It was a net loss,” said Edwards, “that New Haven is probably still trying to recover from.”


Yet up until around 2005, according to Piscitelli, the deputy economic development administrator and former director of the city’s Transportation, Traffic & Parking Department, New Haven put serious consideration into one day extending the Oak Street Connector. It wasn’t until 2007, with the publication of the Future of the Route 34 Corridor Study prepared by Clough Harbour and Associates, that a proposal to scrap the highway altogether garnered real attention.

Then, in 2010, the breakthrough came. A provision of the federal stimulus package passed in 2009 allotted for a discretionary grant program, called TIGER, to help fund major transportation improvements that would strengthen the economy of a specific region and increase the competitiveness of the nation as a whole. After failing to land a 40 million dollar grant in the first round of the program in early 2010, New Haven submitted a revised application that called for 21 million dollars in grant money. In October of that year, the city won one of 42 available TIGER II grants for its Downtown Crossing proposal. There were 1,000 total submissions.

Some critics of the Downtown Crossing have decried the federal government’s involvement in the project, and have drawn parallels between this initiative and federal support of Mayor Lee’s urban renewal programs. Though the federal government is not directly involved in the designs, all aspects of the plan eligible for federal funding must be approved by the Federal Highway Administration in order for the grant to be awarded. But Piscitelli indicated that the speed and scale at which this project is being implemented would not have been possible without the federal government’s involvement. Traditional state and city funding is largely based on a “fix-it first” approach, said Piscitelli, a manner which is not conducive to the dramatic transformation city officials hope the Downtown Crossing project will be. Upon news that New Haven’s proposal had won one of the highly-competitive grants, Mayor DeStefano summed up the collective excitement by borrowing a line from Vice President Joe Biden. “We think this grant is a big fucking deal,” he announced.

Even for those deeply involved on the Downtown Crossing proposal for Route 34, visualizing the scope of the changes can be difficult. Jim Travers, the current director of Transportation, Traffic & Parking said, “It’s hard to envision this blank canvas filled up with office buildings.” Much of that has to do with the way Route 34 looks now: Sunken below ground level, it’s a road you can hear before you see. As North and South Frontage Roads—which flank the corridor—rise across Church Street, Route 34 dips, carving into the ground a canyon of cars. Filling in the gulf and developing on top of it, then, is like turning the landscape inside out.

North and South Frontage Roads will be converted into urban boulevards from Union Avenue to College Street, and local connections will be reconfigured at grade, thereby eliminating the desperate reconstruction needs of the College Street Bridge, which will have nothing to span once the ground is raised to its level. Along with these structural changes, the grant-winning 2010 design, which was prepared by a consulting team led by the firm Parsons Brinckerhoff, calls for special provisions for bikes and pedestrians, anticipates a decrease in automobile congestion, and projects tremendous accompanying job growth.

As a city, New Haven has resigned itself to the fact that manufacturing jobs are not coming back, even with the redevelopment of Route 34. “The city was built with manufacturing jobs, but now the jobs that are available aren’t laborer jobs—they are jobs with your mind,” Travers told me in an unassuming conference room at the Department of Transportation. Flipping through concepts of the Downtown Crossing, he stopped at the images for 100 College St.; it is where the first parcel of developable land will be configured.

Travers showed me a picture of a modern building with a glassy façade. Segments of the walls smoothly angle inward in sweeping planes, conveying a sense of openness and accessibility that stands in contrast with the imposing modernist buildings that currently sit nearby. On the ground floor, there is independent retail with outdoor seating that invites diners and passerby alike. Though the model is still being finalized, the 100 College St. building embodies many of the aesthetic sensibilities that the Downtown Crossing project hopes to imbue into the area: a welcoming, approachable atmosphere within walkable space.

To the delight of the city, the 100 College St. site has a developer. Winstanley Enterprises, based in Concord, MA, and already the developer of New Haven’s largest private medical science buildings, will put an estimated 140 million dollars into the building. (This is on top of the half million Winstanley previously donated towards the 32 million dollar Downtown Crossing project.) Reflecting on the pieces that have come together to initiate the Downtown Crossing redevelopment, Piscitelli said, “The ability to align a plan with people who want to build is a rare and special moment.”

But what Winstanley’s interest in the area truly represents is a commitment to the “jobs with your mind” that Travers emphasized. Above the first level retail floor, the tenants of the 100 College St. building are expected to be primarily biotech and medical firms. The city is banking on an influx of biotech companies to join the suite of firms that have already taken up residence in the New Haven’s medical district. With the Yale/New Haven Hospital and the Smilow Cancer Hospital in place, officials are hopeful that area has the seeds necessary to sprout a biotech revolution.

The centerpiece of the city’s offer to the biotech industry is the Downtown Crossing redevelopment. By transforming the corridor into a walkable and aesthetically pleasing district, New Haven will have its own modern, attractive, urban community. “The most important focus,” said Rae, “is allowing people with businesses and business ideas a well-structured environment in which to make their decisions.”

As the six-lane Route 34 highway is converted into a series of urban boulevards, the process will effectively re-knit the city; it will enact the long-sought remarriage between Yale University and the Medical School, between the University and downtown private enterprise. If the Downtown Crossing succeeds, it has the potential not only to reconnect the city, but to immeasurably enhance the Yale-New Haven brain trust. Elizabeth Benton, BR ’04, the Director of Communications at the Office of the Mayor, said that re-stitching the city “creates a nexus for thought.”

It will also be a nexus of job creation. Depending on the size of the building, the 100 College St. site will produce up to 1,000 permanent jobs. If estimates hold true, Piscitelli said, then when Downtown Crossing is entirely completed, 4,000 permanent, full-time jobs will have been created. Earlier, Rae told me that “3,000 incremental jobs would be a home run.”


A strange thing happened near the end of every discussion I had with someone involved in the Downtown Crossing proposal. After hearing about the tremendous possibilities for job growth, biotechnology, and reconnecting communities, I asked each interviewee about his or her personal level of enthusiasm. Nearly everyone paused, and all of the responses were couched in terms of “potential” and “if properly executed”; no one told me outright that Downtown Crossing would save New Haven’s city center.

Even so, I believe there’s a good chance that many of the people I talked to feel that it will. Tempered enthusiasm may be the last vestige of the Oak Street Connector, a project so clearly designed—with its slum-gutting and road-building—to simultaneously renew and reinvent New Haven. Its failure not only signaled the death of urban renewal as it was practiced in the city, but also the end of boundless expectation. Yet Downtown Crossing is the city’s chance at redemption, even if no one will say it is.


At the end of our meeting, Piscitelli offered a statistic that I hadn’t yet heard. “New Haven’s population grew from 2000-2010,” he said. “It was the first time since 1910 that the city’s population grew at a faster pace than the state as a whole.” There is a strong belief among city officials that now is the time to recreate downtown New Haven, and that in doing so, the city will attract not only jobs but residents.

Still, there are some kinks to work out. Chapman foresees significant traffic problems as Route 34 is converted from a highway to a network of urban boulevards. “When a super highway configuration is replaced with a surface street with intersections, there is a loss of capacity by a factor of 4 or 5,” he wrote in an email.

On the opposite end of the spectrum, there are those like Elicker, the Ward 10 alderman, who believe that too much is being done to accommodate vehicles at the expense of pedestrians and cyclists. His legislation that passed in November is a strong nudge to the city to prioritize alternative forms of transportation in the Downtown Crossing redevelopment. “We should be designing streets for the users who are using them the most, and not for a short time period every day,” he said.

And then there are those for whom enthusiasm towards the biotechnical industry is more restrained. “Somewhere between 80 and 100 cities aspire to be centers of biotech—New Haven is probably in the middle of these,” Rae said.

The city has until September to finalize the plans, at which point they will be re-approved by the state and federal government; construction is expected to begin not long after. It can be easy to miss the remarkable unity of vision between citizenry and city officials amidst the army of small details that are up for debate, which is why Elicker emphasized that “the same people who were promoting his resolutions were advocating for the project in the first place.” As the Downtown Crossing design moves into its final stages, the debate over who the city is for—businessmen, residents, commuters, pedestrians—is increasingly bordering on a consensus. Likely due in part to the harrowing number of businesses and families forced out to make room for the original Oak Street Connector, the district being built in its stead—the Downtown Crossing—is being billed as a place for everybody. “After all,” Edwards told me, “New Haven is the only city whose name is what it is.”

3 Responses

  1. Frank Chapman says:

    Extremely well written article. I would have added that the 60,000 cars per day to be carried on the expressway are now crowded onto George, West Chapel, Edgewood, Elm, Valley, Blake, Goffe Terrace, Howard, Kimberly, Fountain and other residential streets. Lesser (rush hour) traffic jamb avoidance traffic is on East Chapel, State, Willow, Orange and even Whitney Avenue. Residents in these neighborhoods should have had a “vote” as to whether the expressway option was to be pursued.

  2. Frank Chapman says:

    Extremely well written article. I would have added that the 60,000 cars per day to be carried on the expressway are now crowded onto George, West Chapel, Edgewood, Elm, Valley, Blake, Goffe Terrace, Howard, Kimberly, Fountain and other residential streets. Lesser (rush hour) traffic jamb avoidance traffic is on East Chapel, State, Willow, Orange and even Whitney Avenue. Residents in these neighborhoods should have had a “vote” as to whether the expressway option was to be pursued.

  3. brownie says:

    New Haven means Yale. And gentrification…for Yale’s benefit.

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