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The Downtown Partnership takes interested Supporter and Sponsor level 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 each project below.
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BOSTON PUBLIC GARDEN
Origins: From Mudflat to America's First Botanical Garden
Dating back to 1839, the Boston Public Garden is the first public botanical garden in the United States. Its origins, however, are humble. Originally, the land on which the garden sits was marshland. In 1821, citizens built a dam to attempt to turn the land into useful territory, but only succeeded in making acres of mud.
The original idea for creating the Public Garden came from a plan submitted by 17 Boston Brahmins — private individuals who envisioned a formal botanical space adjacent to the already-existing Boston Common. The land was officially designated for permanent public use in 1852. The garden's Victorian design — with its meandering paths, cast-iron fencing, ornamental plantings, and central lagoon — was laid out by George Meacham, who won a design competition for the project.
Two centuries separate the creation of Boston Common and the Public Garden, and what a difference that period made. The Common, created in 1634, was practical and pastoral. In contrast, the Public Garden was decorative and flowery from its inception — featuring meandering pathways for strolling, with the Victorians ushering in vibrant floral patterns utilizing new techniques of collecting, hybridizing, and propagating plants.
Two beloved features were added in the decades that followed: the Ether Monument, the first sculpture placed in the Public Garden, designed by John Quincy Adams Ward in 1867, and the Swan Boats, designed by Robert Paget, which began operation in 1877. The Swan Boats remain one of Boston's most iconic attractions to this day.
The Garden's Role in Shaping Back Bay and Boston's Urban Form
The Public Garden's impact on Boston's physical development has been profound and lasting. The filling, design, and development of Boston's Back Bay was partly organized around the Public Garden — a grid centered by a tree-lined pedestrian mall emanating from the Public Garden became the organizing element for the plan, providing connectivity to adjoining communities and a green spine to the district.
The state government, wanting to build an upper-class neighborhood beyond the Public Garden, was influenced by the threat that the Boston City Council made to sell the garden to housing developers — a move that would have significantly reduced the desirability of the area for the upper-class elite the state was hoping to attract. In other words, the Garden's very existence helped determine that Back Bay would become one of Boston's most prestigious residential neighborhoods.
Ultimately, the Public Garden's small footprint wasn't enough to satisfy the needs of a growing urban city. By the late 1860s, proposals for an extended park system gained popular support, leading to what became Boston's Emerald Necklace park system — with the Public Garden serving as one of nine parks in the 1,100-acre chain of green spaces linked by parkways that Frederick Law Olmsted designed.
Decline and Revival
As the city of Boston entered a time of drift and stagnation after World War II, the Garden and other parks suffered from neglect through the 1950s and '60s — until the once-proud jewel of the city was almost beyond saving, its bridge unsafe, its fountains inoperable, its fencing gone or falling down, many trees diseased, and its staff so reduced that nearby residents offered rakes and hoses for maintenance.
This decline gave rise to a pivotal civic moment. In 1970, a group of local Bostonians founded the Friends of the Public Garden in response to the parks falling into disrepair. Henry Lee, a schoolteacher, was asked to chair the new organization and held 30 people in his home for their first meeting. Within the first year, membership grew from 30 to over 500.
The Friends' first major test came quickly: the Park Plaza Urban Renewal Project in the mid-to-late 1970s proposed building towers over 400 feet tall along streets bordering the Common and Public Garden. The Friends fought it, citing that the towers would cast shadows over the parks, destroying plant life and deterring visitors— and they won.
How It's Managed Today
The Public Garden is managed jointly between the Mayor's Office, the Parks Department of the City of Boston, and the non-profit Friends of the Public Garden.
The Boston Parks and Recreation Department grows all the plants used in the Public Garden in their own greenhouses — over 80 species cultivated for future plantings in the Garden and more than 50 other locations around the city.
The Friends of the Public Garden operate with a 10-person staff and a nearly $4 million budget, augmenting city work and maintenance on the Public Garden, Boston Common, and the Commonwealth Avenue Mall. The Friends oversee approximately 1,700 trees across the three parks they steward, with the beloved lagoon willows being especially vulnerable as the climate grows wetter and stormier.
The Friends have also become a powerful civic advocate. Their steadfast opposition to a proposed development was a major factor in the city negotiating a $56 million fund from a developer for both Boston Common and Franklin Park, helping underwrite a master plan for both parks.
Legacy and Lasting Impact
The Public Garden was added to the National Register of Historic Places in 1972, designated a Boston Landmark in 1977, and declared a National Historic Landmark in 1987.
Numerous studies show that green spaces in urban settings improve public health, moderate the "heat island effect" of dense cities in a warming world, and bring joy to millions. People tend to forget that Olmsted was a social reformer as much as a landscape architect — and the late 19th century, as today, was a time of rapid technological change and widening economic divides.
The Public Garden's story is ultimately one of citizen determination — from the 17 Brahmins who first envisioned it, to the neighbors who brought their own rakes during its darkest days, to the advocacy group that has fought off overdevelopment for more than 50 years. It remains both the green heart of downtown Boston and one of the most influential pieces of urban parkland in American history.
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DOWNTOWN CROSSING
Located at the hub of downtown Boston's retail and transit activity and covering several blocks radiating from a central T stop, Downtown Crossing has always been a popular location for department stores, specialty stores, and eateries. With a subway station at every corner, including the prominent Park Street and Downtown Crossing stations, thousands of people experience the historic streets of the district daily. It sits at the intersection of Washington, Summer, and Winter Streets, just steps from Boston Common and the Financial District.
In the early 1900s, Temple Place in the heart of Downtown Crossing could have been considered the Fifth Avenue of Boston — the street was famous for its shows and women's fashion.
The area was anchored by two of New England's most celebrated department stores: Jordan Marsh and Filene's, including the legendary Filene's Basement, which became a cultural institution in its own right. For generations, Downtown Crossing was the undisputed commercial heart of the city.
Postwar Disinvestment and the Pedestrian Mall Gamble
The neighborhood took a nosedive after World War II, becoming a place that was lonely and desolate after dark, despite the daytime shopping bustle. White flight, suburbanization, and the rise of suburban malls pulled investment and shoppers away from city centers across America — and Downtown Crossing was no exception.
To reverse the trend, following the success of the Faneuil Hall Marketplace, Boston decided to redevelop the Washington Street area into a pedestrian-only mall, which was unveiled in 1979. At first, foot traffic and business in the area declined, but it slowly returned as the popularity of the mall as a shopping area increased, helped along by a cart vending program.
The recovery proved fragile. By the turn of the millennium, once-great commercial retail institutions like Jordan Marsh and Filene's had closed their doors. Jordan Marsh became a Macy's in 1996, and Filene's closed its landmark flagship in 2006. Over time, the gutted interior of the historic Filene's building became a symbol of decline in Downtown Crossing — a hulking, fenced-off hole in the ground at the neighborhood's most prominent corner, sitting vacant for years.
Urban Management to the Rescue
The single most important institutional force in stabilizing and reviving Downtown Crossing has been the Downtown Boston Alliance (DBA), formerly the Downtown Boston Business Improvement District (BID).
The Downtown Boston Business Improvement District is Boston's first BID and one of only six in Massachusetts. A binding assessment levied on all commercial property owners based on property value funds BID activities. A 33-member board of directors elected by BID members oversees the organization, representing the cross-section of Boston's business and residential communities.
The DBA's mission is to significantly improve the experience of all who live, work, visit, go to school, or shop in the 34-block, 100-acre service area by providing supplemental services to keep the district clean, safe, and vibrant while catalyzing an energetic and thriving business climate and serving as the neighborhood's voice and advocate.
The DBA deploys several key urban management tools:
From Retail Hub to Mixed-Use Neighborhood
The most dramatic physical reinvention of Downtown Crossing came with the redevelopment of the old Filene's site. Millennium Tower, a 60-story, 684-foot residential skyscraper, was built on the site of the former Filene's flagship store. Construction began in 2013 and was completed in 2016, containing 442 condominiums, a Roche Bros. grocery store, and Class A office space.
When Millennium Tower opened in 2016, there was enormous excitement — at 685 feet, it was Boston's tallest residential building, featuring an indoor swimming pool and a well-appointed lounge, promising to alter the city's skyline and revitalize Downtown Crossing.
The pandemic, however, dealt a new blow. Following the release of a Downtown Revitalization Report in October 2022 that showed post-pandemic commercial office space vacancy rates of approximately 20 percent, city planners began exploring residential conversions as a pathway to restore vitality.
In July 2023, Mayor Michelle Wu launched a Downtown Office to Residential Conversion Pilot Program, using property tax breaks of up to 75 percent of assessed value for 29 years to incentivize property owners to convert office space to apartments or condos.
New zoning approved by the BPDA Board strengthens protections for Downtown's historic and cultural assets, streamlines pathways for adaptive reuse of buildings, and enables housing and mixed-use density that Downtown needs to grow as a vibrant and more inclusive neighborhood. Meanwhile, in June 2024, Suffolk University purchased 101 Tremont Street for $30 million with plans to convert it into a dormitory — a sign of the diverse reuse strategies now reshaping the area.
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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.
BOSTON SEAPORT
History
The neighborhood first began to take shape in the 1850s as an industrial zone built on landfill, largely shaped by train tracks, freight terminals, and industrial fishing piers. In the early 1900s, the area came alive with ships delivering goods to nearby factories, making it one of Boston's busiest commercial ports. But the mid-1900s brought steep decline — factories shut down or relocated, and the area became known for empty lots and abandoned buildings.
Beginning in the 1990s, two unprecedented public investments — the Big Dig and the Boston Harbor cleanup — sparked new interest in the largely vacant waterfront property just a short distance from the Financial District. The $14.6 billion Big Dig buried the formerly elevated I-93 interstate, which had previously cut off the waterfront from the rest of the city, and extended I-90 eastward through the Seaport all the way to Logan Airport.
In addition to the Big Dig, the construction of the John Joseph Moakley Federal Courthouse at Fan Pier and a new convention center helped set the stage for private development. The Fort Point warehouses became home to tech startups, art studios, and creative businesses drawn by lower rents and open floor plans.
The Innovation District
In January 2010, Mayor Thomas Menino launched an initiative dubbed the "Boston Waterfront Innovation District" — a plan to take approximately 1,000 acres of underdeveloped South Boston waterfront and create a work/live/play environment designed to attract technology and innovation companies.
The site was master planned by Morgan Stanley and Gale International starting in 2006, with WS Development joining in 2007. By 2015, WS Development assumed the role of lead developer and completely redesigned the master plan, with the philosophy that "this is not a development project; this is the creation of a neighborhood."
WS Development is a Boston-based private real estate company with deep roots in the region. While the company built its reputation primarily as a retail and mixed-use developer across New England, its involvement in the Seaport District has elevated it into a different league entirely — becoming the steward of what is now the single largest active private development project in Boston's history.
While WS Development isn't the only developer operating in the Seaport, the company became a dominant force in 2015. Navigating the project required addressing decades of infrastructure planning, layered regulatory requirements, complex agreements with multiple public entities, and extensive environmental and zoning challenges — including land control issues, infrastructure relocation, and multiple layers of public approvals — all rooted in the legal legacy of the Big Dig's Central Artery/Tunnel Project.
WS transformed 33 acres of land, composed of 7.6 million square feet of residential, hotel, office, retail, entertainment, civic, and cultural uses, as well as signature public open spaces. The project represents the single largest active development project in Boston's history. The Seaport is now home to an ecosystem of more than 350 companies, from global leaders in technology and biotech to groundbreaking startups, following a decade of development and $22 billion of public investment.
The Philosophy: Creating a Neighborhood, Not a Project
From the outset, WS articulated a philosophy that distinguished its approach — at least in aspiration — from typical corporate real estate development.
"We try always to remember that this is not a development project; this is the creation of a neighborhood," said Yanni Tsipis, senior vice president of Seaport development at WS Development. "This is a piece of a great American city, and great cities are composed of great streets, public places, and social spaces that happen to have buildings built between them. That is a very important philosophy for us as the stewards of the Seaport."
In assuming stewardship of the remaining undeveloped blocks, WS Development saw the opportunity and the responsibility to elevate the neighborhood to standing among those of other world-class cities — by cultivating activity, vitality, and a strong neighborhood identity. The Public Realm: Harbor Way and the Paseo
The centerpiece of WS's public realm strategy is Harbor Way — a pedestrian promenade designed to knit the Seaport together and connect it back to the water. Harbor Way is a linear promenade and central public park that carves pathways through the site. Landscape architect James Corner — whose firm is known for New York City's High Line — calls it "a pedestrian armature" designed to connect the city to the harbor. "The tendency for developments at this scale is the developer is always wanting to internalize the project, to turn it inwards," Corner explained. "I always find those places bereft of urban life. They're often empty and sterile simply because they're not connected to anything."
Central to the master planning effort was creating a landmark "urban room" — with Harbor Way Square Park at its heart featuring a large central lawn — and a 21st-century neighborhood experience, with 39% of the total project area exclusively devoted to pedestrian-only open space. The individual buildings also contribute to public life at the street level. One Boston Wharf features the Boston Wharf Paseo — a street-level interior public promenade lined with shops, cafes, and public art installations leading from the Fort Point Channel Landmark District to a new one-acre public space called The Rocks at Harbor Way.
WS has positioned sustainability as a defining feature of the Seaport portfolio. One Boston Wharf is a 707,000-square-foot, 17-story mixed-use building that will be Boston's largest net-zero-carbon office building, reducing greenhouse gas emissions by more than 90% below code requirements and eliminating 5.1 million pounds of CO2 emissions annually.
The building features water reclaimation systems, air-source heat pumps, advanced energy recovery technology, and state-of-the-art building management systems. It also marks the first commercial placement of Sublime Systems' zero-carbon cement and has achieved LEED v4 Platinum certification. Buro Happold Amazon has leased the entirety of the office space, creating a total footprint of over 1 million square feet within WS Development's Seaport development.
One Boston Wharf also includes a long-planned performing arts center with a 500-seat performance venue and a more intimate 100-seat venue, catering to local Boston arts groups — one of the few major civic spaces in the fast-growing Seaport district.
The Criticisms: A Gleaming, Unequal Neighborhood
For all its ambition, the Seaport under WS Development and its predecessors has attracted criticism. The Seaport has been criticized for its inhuman scale, lack of civic spaces, poor transportation and connections to the rest of Boston, and lack of affordable housing. The growth has also all but eradicated what was once a vibrant arts community in the adjacent Fort Point neighborhood.
The deepest criticism is racial and economic. The city redeveloped the Seaport District over the past decades, but never with an eye towards creating an integrated neighborhood. The results show: a largely white, largely affluent new neighborhood has risen in the city's midst. There are no schools and no homes priced within reach of the average Bostonian.
The district stands as perhaps the region's most vivid illustration of what a luxury-dominant development corridor delivers: glass towers, high-end fitness studios, trendy restaurants, and a conspicuous absence of everyday fixed infrastructure.
The Bottom Line
WS Development has delivered something genuinely impressive by the metrics of private real estate development — a massive, architecturally ambitious, increasingly sustainable mixed-use district built from scratch on what was once a wasteland of parking lots. Their commitment to public realm, Harbor Way, and net-zero sustainability sets real benchmarks for urban development.
Today it is home to major companies like Amazon and Vertex Pharmaceuticals, alongside residential developments, cultural institutions, and modern architecture that has reshaped the city skyline. In short, it went from a forgotten industrial wasteland of parking lots to one of America's most prominent urban redevelopment success stories — driven by public infrastructure investment followed by a wave of private development.
But the Seaport also represents the limits of what private development — even well-intentioned, thoughtfully managed private development — can achieve without stronger public policy mandates for affordability, equity, and integration. The neighborhood WS built is extraordinary for those who can afford it. The harder question Boston continues to grapple with is who it was actually built for.
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