Why Is It So Hard to Get a Good View in Boston?

One of the joys of living in a modern, skyscraper-studded city is getting to see it from above. Now that there are only two observation decks left in Boston, here’s a case for building more rooms with a view.

Illustration by Nigel Buchanan

On a warm day earlier this fall, I left home on my bike with a simple goal: to get a decent view of Boston. After 18 months of rattling around my corner of Cambridge during the pandemic, I found myself yearning for the urban connection and sense of place you can only get from looking down at a city from a great height.

What’s more, I knew firsthand that, like seeing a landscape from a mountaintop, getting up above the hustle and bustle of a city and gazing out has a calming, therapeutic effect. Before moving to the Boston area, I worked for a magazine in New York that had its office at One World Trade Center. Whenever I needed a break from the frantic rush to close an issue, I’d head up to the employees-only lounge on the 64th floor, look out at the skyline and beyond, and feel my pulse steady and my breath deepen.

While I knew the Prudential Tower’s observation deck was closed for renovations, I wasn’t prepared for how insurmountable the challenge of getting my bird’s-eye view would prove to be. Wow, was I wrong. I rode over to the Bunker Hill Monument, but upon my arrival I immediately realized I’d need to come up with another plan. A flock of tourists were gathered around the base of the granite obelisk, reading a National Park Service sign stating that the monument remained closed due to COVID concerns. I coasted back down the steep hill on Monument Avenue, resolved to head across the Charles and try my luck instead at Boston’s original skyscraper: the Custom House.

When I arrived, I found no signs outside touting the observation deck, nor directions about how to get upstairs. Flustered, I approached the front desk and asked the clerk for help.

“Are you a guest?”


“Well then, do you have an appointment?”

I did not.

“We take people up there once a day at 2 o’clock, but you need to call ahead to reserve a spot.”

I checked the time and saw it was already almost 3 p.m. Stumbling back outside, I checked my phone for other options, but other than the closed Pru Skywalk, there were no observation decks in town.

Defeated, I got back on my bike and headed home. My route took me past some of the city’s recently erected skyscrapers, including Millennium Tower and One Dalton, which respectively stand at 60 and 61 stories high. What I would do to get a view from either of those, I thought to myself. More to the point, I wondered how on earth it was that after a decade or so of unprecedented building and construction, in a place that likes to think of itself as an ascendant, major metropolis, there were hardly any decent observation decks or places from which to view our city?

Several weeks before my aborted sightseeing trip, the Boston Globe reported that the advertising guru and philanthropist extraordinaire Jack Connors was giving up his office at the top of the city’s tallest building, the Hancock Tower, for new digs on Newbury Street. When I called him, Connors spoke wistfully of the vistas that his perch, with its floor-to-ceiling windows, had long afforded him. “You can see the movement in the city,” he recalled. “When there’s a fire, you’re among the first to see it. When the weather changes, you can see it coming in from the west.”

Hundreds of thousands of people each year used to be able to enjoy the very view that Connors remembers so fondly, including seeing a city in motion from on high. But over time, Boston’s tallest point went from being a public amenity to the private domain of one of the city’s most powerful people.

Observation decks were key selling points for both the Prudential Tower and the Hancock Tower when construction started in the 1960s. Both of these popular destinations remained opened until 9/11, when, along with many other skyscrapers across the country, they closed due to security concerns. While the Pru’s Skywalk reopened in the weeks after 9/11, the Hancock’s never did. Instead, the building owners used it for private functions and announced it would be converted into office space.

By 2005, City Councilor John Tobin was demanding to know how this had happened, claiming that an observation deck had been a necessary precondition for the Hancock being built in the first place. In response, the building’s owner stonewalled the press, other city officials shrugged their shoulders, and Mayor Tom Menino played innocent, later telling reporters, “I haven’t seen the document.” Lauren Shurtleff, the current director of planning at the Boston Planning & Development Agency (BPDA), says her office was never able to find any paperwork documenting the requirement that the building have a public observation deck. And just like that, one of the city’s loftiest attractions vanished into thin air.

As in other cities, Boston’s skyline has changed dramatically over the past two decades, but Boston may be the only city that has seen so much building without a new observatory also taking root.

What makes the loss of the Hancock’s observation deck all the more upsetting is the fact that it hasn’t been replaced by any new ones. As in other cities, Boston’s skyline has changed dramatically over the past two decades, but Boston may be the only city that has seen so much building without a new observatory also taking root. The massive Hudson Yards development in Manhattan, for instance, debuted “The Edge,” a glass-floored, outdoor deck 100 stories up in 2020—in a city that already has its fair share of high-rises with public lookouts. The previous year, San Francisco’s Salesforce Tower opened up the highest floor on the West Coast for monthly tours. Even the relatively meager skyline of New Orleans will boast an observatory soon, thanks to the renovation of a historical 33-story tower that Gary Johnson, president and CEO of architectural firm CambridgeSeven, is helming. “When a developer chooses to devote that prime real estate to public benefit,” Johnson told me, “it’s an incredible gift to the city.”

It doesn’t have to be a gift, though. BPDA could insist on observation decks, the way it supposedly did when the Hancock Tower was approved—and make sure there is a paper trail to document it. In fact, Shurtleff assured me, the city is as keen on observation decks as I am. “Anytime a project comes through [for a tall building],” she tells me, “it’s like, ‘Okay, can you have an observation deck?’”

Apparently, however, the answer is always no. Johnson was the architect for One Dalton, the third-tallest building in the city, which went up in 2019 without an observation deck. “I don’t think we ever had a conversation about it,” he told me, explaining that the tower had a small footprint, giving it little room for a dedicated elevator to get visitors up to the top.

More controversial were the negotiations over Winthrop Center, a two-tower complex near South Station that is slated to top out at 691 feet next year, making it the fourth-tallest building in Boston. That project site was owned by the city, meaning BPDA had the power to ensure that whatever got built maximized public benefits. The agency specifically asked for a new observation deck in its call for proposals, and three of the six bids included one. In the end, BPDA selected Millennium Partners to develop the site. Instead of the observation deck that the city says it wanted, Millennium’s plan included a “Great Hall,” a multistory corridor with soaring ceilings that would connect Devonshire and Federal streets and be open to the public. Then in 2019, the “Great Hall” was revised into “the Connector,” with the multistory loft areas disappearing from the plans and the ceiling being lowered closer to the ground. In lieu of an observation deck atop one of Boston’s newest skyscrapers, we got a lobby that doubles as a cut-through.

And so it goes. Each time a tall building gets proposed, the city asks for an observatory and then doesn’t insist upon it when the developer says no can do. Rinse and repeat for about a decade, and you end up with our skyline, the highest reaches of which are all but closed to the very people who live here.

Boston’s need for more observatories goes far beyond my and other residents’ desire to feel that special connection and sense of context that only a bird’s-eye view can provide. It’s also about our identity as a city—no longer merely a low-slung, quaint, historical town, but a sleek and modern metropolis. “Having an iconic tall building lets you know the city has arrived on the global stage,” says Daniel Safarik, assistant director of research and thought leadership at the Chicago-based Council on Tall Buildings and Urban Habitat. “Offering an observatory there allows visitors to feel like they are a part of that arrival.”

Likewise, when a city loses an observatory such as the Hancock’s, the blow is greater than the sum of the disappointments among residents and tourists who are cut off from the views. The city itself suffers, Safarik says, adding that “Observation decks are like any large private investment that has civic implications. When a city loses a major league sports team, the city loses [a sense of its importance]. If you have an iconic building that doesn’t have an observation deck, there’s some aspect of that city’s profile that’s lost, too.”

I’d also argue that observation decks don’t only help people feel connected to their city, but to the buildings themselves. Let’s be honest, the reason the Pru is such a beloved icon in Boston isn’t because of its, well, questionable design. Nor is it because of the mall. The Pru is part of the fabric of the city because of the unforgettable experiences it’s provided the people who have been to the top of it and have seen their city laid out in miniature beneath them.

For the time being, we are left with two choices. We can hold out until 2023, when the replacement for the Skywalk and Top of the Hub is set to open. Rebranded as “View Boston,” the top of the Prudential Tower will become a three-floor attraction with panoramic windows and an indoor/outdoor cocktail lounge. Or, we can content ourselves with our current offering—a 26-story lookout, by appointment only.

I couldn’t do either. So a few weeks after my failed excursion to the Custom House, I returned—this time with a reservation. When I arrived, there were already two parties at the front desk: a man in a windbreaker and a bald dad in an Almost Famous T-shirt shepherding two teenagers glued to their iPhones. At 2 o’clock sharp, a security guard squeezed the five of us into a guest elevator that crawled its way up to the 19th floor. We then transferred to a slightly more spacious lift that carried us to the 26th level. From there, we were led outside to a barebones viewing platform that wraps around the building above the clock face.

Though only about half as high as the Pru’s top floor, this observation deck nevertheless offered an impressive perspective on the city. Wind whipping my face, I marveled at the harbor’s breadth, at the juxtaposition of the red-brick enclave of the North End against the glassy new high-rises near the Zakim Bridge. I was likewise riveted by how my high remove allowed me to simultaneously experience all of the little incidents that make up the life of the city. I could hear the low thrum of construction and a crowd clapping at Faneuil Hall at the same time a Coast Guard boat blasted its horn in the harbor. A photo shoot unfolded at a park in the North End while window-washers scaled an office building downtown and golden balloons tethered to patio furniture on a nearby roof deck bobbed in the breeze.

Looking west, though, I suddenly felt hemmed in by the skyscrapers of the Financial District. The Charles was barely visible in the gaps between buildings, and the Back Bay was totally obscured, to say nothing of Roxbury, Dorchester, or Jamaica Plain. While this perch did offer some sense of the city as a cohesive unit, it was a limited one, as if I were looking at an old family photograph that had been torn in half.

Just the same, I could still feel some semblance of the tranquility I’d once enjoyed at One World Trade Center. Rather than being overwhelmed by the scale of the city, I found it easier to imagine myself as one constituent part of it, neither more nor less important than any other. If only all of Boston could have this feeling. It’s a sensation everyone deserves, not just the handful who can afford to rent the best views in town. And Boston should be the kind of city that can offer it to us.