2026 Urban Exploration Trip: Rose Kennedy Greenway

The Downtown Partnership takes invited members on an annual Urban Exploration Trip, highlighting projects in a particular city that demonstrate lessons learned that can be applied to active development projects in St. Pete. This year, we are going to Boston to see the Boston Public Gardens, Downtown Crossing, the Rose Kennedy Greenway, and Seaport. Please find more information about the Boston Public Gardens below.

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ROSE KENNEDY GREENWAY

Origins: A Highway Scar and the Big Dig

To understand the Greenway, its important to understand the wound it was meant to heal. In the 1950s, Boston — like cities across America — made a fateful choice to route an elevated interstate highway through its downtown. The John F. Fitzgerald Expressway (I-93) sliced through the urban fabric, cutting off the historic North End, Chinatown, and the waterfront from the rest of the city and casting shadows over neighborhoods below. Boston had a clear plan, tearing down historic working-class neighborhoods to make space for the new roads. Among those lost were portions of the West End, Downtown, and Chinatown.

In 1991, after almost a decade of planning, construction began in Boston on the Central Artery/Tunnel Project, more widely known as the "Big Dig" — recognized as one of the largest, most complex, and technologically challenging infrastructure projects in the history of the United States. The project would remove the elevated highway and create a tunnel system below the city.

As a required mitigation for the project's environmental and urban impacts, state permitting agencies compelled the Massachusetts Highway Department to formulate a joint development plan for the surface parcels overlying the depressed I-93, transforming approximately 17 acres of former highway right-of-way into linear parks and plazas — addressing the original Central Artery's division of downtown neighborhoods and aiming to restore connectivity between areas such as the North End, West End, Chinatown, and the waterfront.

With the elevated highway relocated underground, community and political leaders seized the opportunity to enhance the city by creating The Greenway — a public park that re-connected some of Boston's oldest and most vibrant neighborhoods, and the city itself with the waterfront.

The park was named after Rose Fitzgerald Kennedy, born in the North End in 1890 and remembered as the mother of President John F. Kennedy, Attorney General Robert Kennedy, and Senator Edward Kennedy. The expressway it replaced had been named after her father, former Boston Mayor John F. Fitzgerald — making the renaming a symbolic act of reclamation.

What the Greenway Is

The Rose Kennedy Greenway is a linear park consisting of landscaped gardens, promenades, plazas, fountains, art, and specialty lighting systems that stretch over one mile through Chinatown, the Financial District, the Waterfront, and North End neighborhoods. Officially opened in October 2008, the 17-acre Greenway sits on land created from demolition of the John F. Fitzgerald Expressway.

Almost 900 trees line the Greenway's boulevard. The Central Artery/Tunnel Project resulted in more than 300 acres of open land reconnecting Boston's downtown to its waterfront, with 45 greenspaces and public plazas.

Each section of the Greenway reflects the character of the neighborhood it serves. The core areas include Chinatown Park, Dewey Square, Fort Point Channel Parks, Wharf District Parks, Armenian Heritage Park, and North End Parks — each designed to provide pedestrian connectivity, recreational space, and neighborhood-specific amenities while capping the underlying highway tunnels. The North End Parks, being in the widest section and surrounded by the shortest buildings, achieve the most comfortable human scale and sit at the crossroads of the historic Freedom Trail.

How It Is Managed: The Conservancy Model

The Greenway's governance structure is a textbook example of a public-private partnership for urban park management.

The Greenway is entirely maintained, programmed, and improved not by government but by a non-profit — the Rose Kennedy Greenway Conservancy. This model is common elsewhere for signature parks, such as the Friends of the High Line in New York or the Discovery Green Conservancy in Houston. The public-private partnership has meant that each dollar of foundational public funding has leveraged more than 1.5 dollars of additional private funds.

The 2008 legislation that confirmed the Conservancy as the designated steward established an initial 50/50 public/private funding model. Through a multi-party funding agreement announced in June 2017, public funds from the State and City represent approximately 20% of the operating budget, a Greenway Business Improvement District funds approximately 20%, and the Greenway Conservancy itself generates approximately 60%.

The Conservancy has sole responsibility for managing all aspects of the Greenway, including horticulture, programming, public art, maintenance, and capital improvements. Its vision is a vibrant, inclusive, and evolving gathering place that offers healthy green space, fun, engaging, and thought-provoking experiences, and a testing ground for new ideas.

Programming has been a central pillar of the management approach. The Conservancy has partnered with for-profit and non-profit organizations to develop 400+ free public programs designed to connect people of all backgrounds and generations to each other, the park, the surrounding neighborhoods, and the natural environment — including festivals, concerts, public art, horticultural tours, farmers' and artisans' markets, food trucks, fitness classes, and family programs.

Connecting Neighborhoods: Impact and Success

The Greenway and its distinct parks restored visual and physical connectivity between downtown Boston and several historic neighborhoods, including the North End, Long Wharf, South Station, and Chinatown. For the first time in half a century, a pedestrian could walk comfortably from the Financial District to the waterfront, or from Chinatown to the North End, without navigating the shadow and noise of an elevated highway.

The Greenway is now a key feature of the modern reinvention of Boston, Boston Harbor, the South Boston Waterfront, and the Harbor Islands — serving as a connective tissue that links the city's renaissance zones together.

From "Empty Way" to Civic Success: Did It Achieve Its Goals?

The honest answer is: eventually yes, but not without a rocky start.

When the Conservancy for the public space was first established, it faced a lot of criticism for its use of the land and what was seen as sparse programming — so much so that it was once called the "Empty Way" by critics.

The turnaround came through creative, persistent placemaking. One observer who went from critic to evangelist traced the transformation through moments like the first gourmet food truck rolling into Dewey Square in 2010, artist Janet Echelman's mutable rope sculpture soaring above Congress Street in 2015, and a 3D printer churning out free plastic roosters in Chinatown for the Year of the Rooster in 2017.

Within a few years, the conservancy team invigorated the space with free events, art installations, a beer and wine garden, and other programming that brought out millions of visitors. "It started to be seen as a success — an innovative use of the public space," said former Executive Director Jesse Brackenbury.

Some goals, however, remain incompletely met. Critics have noted that the Greenway was originally intended to be a series of discrete urban rooms framed by medium-size landmark buildings that would cover tunnel ramps and bring activity to the open spaces — but that vision remains far from fully realized, with debates about development height, shadows, and how to generate the active 24-hour street life that would truly animate the corridor

The Greenway's relationship with Chinatown also illustrates its complexity as a social tool. The history and changing nature of Chinatown since the completion of the Big Dig has been a significant focus of community concern — particularly around real estate developments in and adjacent to Chinatown, as the new green space has attracted investment that also brings gentrification pressure.

Despite these tensions, the Greenway has fundamentally altered Boston's urban geography. It facilitates over 10 million annual visitors for transit, leisure, and events — a figure that would have been unimaginable when the elevated highway stood in its place. It has transformed what was one of the most damaging urban infrastructure mistakes of the 20th century into one of the most celebrated examples of urban reclamation in the United States.