I came here with a purpose: to gather with a climate, urbanism, and transportation book club and chat about Inclusive Transportation on two Sundays in two months.

Both times we met in a coffeeshop in The Hollow, a neighborhood that reminds me of Frog Hollow where I live in Hartford.

It’s just north of downtown, and The Hollow is as worlds’ away from it as Hartford’s downtown is to Frog Hollow.

I’m wired to be partial to it — densely populated and diverse.

I’m wary of any pronouncements that a neighborhood is any one particular thing or belongs to any one particular division of people. At home, I still hear that Franklin Avenue or “The South End” is an Italian neighborhood, when in reality much of that population (and it’s associated retail and restaurants) shifted into the suburbs; it’s much more of a Peruvian spot, with lots of everyone else mixed in. My own neighborhood is often described as a Puerto Rican neighborhood, which is also inaccurate, and anyone who lives in Frog Hollow absolutely knows this.

The Hollow of Bridgeport is as much of a mix. In a short walk, you get an Italian bakery; Creole, Ecuadorian Honduran, Mexican, and Portuguese meals; African hair braiding; a mosque. Another writer used “kaleidoscope” to describe Bridgeport’s culture, and I couldn’t have said it better.

Jeff, co-owner of Sound Coffee, began home roasting beans about a decade ago using a popcorn popper. Soon, he leveled up to a home roasting machine that he operated in his garage. He grew this into a business, selling at farmers’ markets, having bean orders delivered by bicycle.

In August 2023, he and his wife, Sarah had the soft opening for the coffeehouse on Main Street in Bridgeport. This came after they spent about nine months searching for a location. They said that Bridgeport was most desirable for them because it’s close to where they live in Fairfield, but with commercial real estate prices more within their price range.

They told me that “when 2040 Main Street became available, we went to look at it and it checked a lot of boxes–on a section of Main Street that’s still fairly intact and walkable and the right square footage. After the tour, Jeff asked Sarah, ‘So, what do you think?’ and she said, ‘Well, it doesn’t feel wrong.'”

Beyond the price and size of the building, Jeff and Sarah appreciate Sound Coffee‘s neighborhood. The buildings are mostly close to the street edge, rather than set back, and there aren’t lots of interruptions between them like vacant or surface parking lots. They say “Some of our neighbors have been in business for over a decade. The nail salon across the streets has been owned and operated by the same person for over 30 years. It felt like a good neighborhood to put down roots and try to become a ‘third place’ for the community.”

Is it part of the community? On both stops, I watched as children associated with a nearby mosque came by. Once was during Ramadan, so they stood outside and waved. The second, after the holiday completed, they brought their energetic selves inside to place their orders. It was obvious by watching and listening that they were regulars. It says a lot that neighborhood kids were comfortable and welcome here, and that the barista was enjoying their presence.

Currently, there is only one table inside, but Sarah and Jeff are working on a grant to help turn a side yard into “into a beautiful 3-season patio.”

The name has a few meanings. Bridgeport is on Long Island Sound.

There’s also the other meaning: “there is a music vibe to the shop, based on how we’ve decorated it. This is a reflection of Jeff’s love of music.”

I have an appreciation for restrooms that are unlocked (no fancy passcode needed), clean, and well-decorated. In the main part of the shop, vinyl decorates the walls. What they have playing is always more interesting than standard retail Muzak. I know because I arrived considerably earlier than the book group and had time to relax and talk with the barista about the lavender latte they made using a syrup that was not one of the mass produced bottles standard at most cafes. I complimented the drink because there was a noticeable taste difference between this and lavender lattes I had elsewhere — all of which had been fine, but this was special. That’s what’s possible in a small, independent coffee shop where the owners are creative and open to experimentation.

Their current summer special is an espresso tonic, either plain or with pink grapefruit. I asked if the specials changed monthly, and they said no, these “change on a whim. Our baristas are very passionate about coffee and love working behind the scenes to develop unique and delicious new drinks for our customers. When they create a ‘winner’ that they love and are excited about it, we put it on the menu.”

The fresher paint job makes the building stand out on Main Street, but it’s about to be even more noticeable. This year, the City’s Office of Planning and Economic Development along with the Bridgeport Downtown Special Services District is expanding their mural program citywide, and Sound Coffee is awaiting theirs. Jeff and Sarah told me “We worked with the mural coordinator this spring to select an artist, which we did, and they should be beginning work sometime this summer. Not sure how much we can reveal before the mural is finished. It’s likely safe to say that the artist is based in Bridgeport, which we love, and the art is inspired by the history of coffee and the people around the world who grow it.”

They’re hoping to celebrate the new mural in late summer/early fall when the coffee shop marks its one year anniversary at this location.

Beyond Main Street, you can also find them at a busy outpost — The Amp. They explained that they “got connected to the Amp indirectly through the University of Bridgeport Accelerator program, which we participated in in 2023. Our first events there were university graduations early in May and since then, it’s been music performances several days per week. During events, we sell a variety of coffee drinks and recently added some coffee cocktails to the menu.”

They didn’t mention, probably because I already knew about, the number of collaborations and pop-ups elsewhere, including Moonsmoke Bakery in Fairfield, Eco Evolution in Norwalk, and Black Rock Books in the Black Rock section of Bridgeport. I respect the hell out of small businesses that operate through collaboration, coordination, and cooperation.

I could have made this trip simply for the coffee, but I didn’t, and in either case, the train station is downtown and Sound Coffee is north of there.

So, when I say that The Hollow is another world from Downtown, part of what I’m referring to is the giant mental block created by Route 8 which divides them. There are crosswalks and even pedestrian signals, but it takes lots of figuring out because the walking routes do not appear obvious. This is coming from someone whose regular work commute involves walking under the Aetna Viaduct. I know how it feels to have this kind of eyesore and obstruction in my neighborhood, and how it feels when the convenience of those passing through on the highway is prioritized over the health, comfort, safety, vibrancy, and convenience of those living in neighborhoods sliced up by highways.

Is Downtown Bridgeport walkable?
Yes, in that you can literally walk from the train station to other points in and out of downtown.
Is it an enjoyable walk?
That depends.

Following Main Street between The Hollow and Downtown is whiplash. The animated landscape of restaurants segues into body shops and a giant car wash, then into the highway ramp area, and then a park.

None of the times I passed Majestic Park did I see anyone in it, even when the flowers were blooming. Considering that there are apartments across the street and next to this park — the park path connects into one of those apartment complexes — the absence of people was a super weird vibe. It’s mostly a short path that leads to benches and memorial for victims of violence. It’s not like a trip to Harkness or anything, but where were the people walking their dogs? Where were the folks sitting on benches?

There are few parks in this part of Bridgeport; if you’re hoping for the full Park City experience, look at a map and plan accordingly.

Walking through downtown Bridgeport on a Sunday morning feels like walking in downtown Hartford ten years ago, before we had the kind of leadership that really focuses on having a downtown that exists for everyone — not just for the M-F commuters.

I’ll get back to that momentarily.

What would it be like if the urban narrative, specifically of the downtown, was not tainted or haunted by an incessant cycle of scorn, ridicule, and experimentation by suburban decision-makers with a savior complex? What would it look like if decision-makers deeply cared about their community and expanded their ideas about who was within that community? This is a question to ask about many places, and here, I ask it about Bridgeport.

Back in 1996, the New York Times ran a piece that exemplifies the issue: “The idea of expanding arts and entertainment [in Bridgeport] actually originated in 1993, but was drowned out by the quest for a casino and Donald Trump’s proposals for an amusement park and a motor racetrack, among other noisy ballyhoo.”

That casino quest was in 1994, when Trump said he’d spend $1 billion on a casino-entertainment complex.

What happened?
You know without knowing if you’ve paid attention to anything Trump-related: bluster.

He sat on land and owed a ton of back taxes. To get out of paying those taxes, he did a $1 (one dollar) land transfer. This land wound up being used for a baseball stadium – Harbor Yard. That happened after the State of Connecticut authorized $14 million in bonds to build it. The Bridgeport Bluefish, a minor league team, were touted for a while as what would save Bridgeport.

Does this sound familiar?

They lasted from 1997 until 2017.

In 2021, the ballpark was renovated and reopened as a large concert venue, visible from the train.

I understand what I am asking when I turn this to Bridgeport: why continue falling for the same thing – those who are only interested in their own money and power while delivering absolutely nothing to you, or the re-election of a mayor who was convicted of racketeering and extortion? Why do we – in Hartford and Bridgeport – have so little self respect that this is who we accept as “leadership”? Why don’t we think we can do better?

Fred Musante, writing in the 1996 New York Times, said “Their biggest problem now is that no one stays in downtown Bridgeport after work, or thinks of visiting there during leisure hours.”

When I say that downtown Bridgeport reminds me of downtown Hartord ten years ago, this is what I’m talking about. Residents would be out, at least, in Hartford — but visitors? Maybe they’d come for major events or the art museum. That was it. You could only get coffee on the weekend at a Dunkin Donuts and that one coffee shop on Pratt Street that then moved all of its energy into its second location in New Haven, and predictably, closed up its original location to focus on what seemed more promising. Right now, we have at least six non-Dunkin, non-Starbucks cafes open in downtown Hartford on the weekend. I’m sure I’m forgetting some. The point here is that there was a shift.

My whole wandering through downtown Bridgeport was infused with the spirit of wanting to believe, in rooting hard for the underdog. It was looking for signs that some change was stirring.

I know that Berlinetta Brewery gets hopping, later in the day. Friends have said as much, and photographic evidence exists. Nearby, the Skateport space is sometimes activated with people roller skating outdoors. Wander by when neither the brewery nor rink are open, and there’s tumbleweeds. At least that was my experience.

Years back, before the Housatonic Museum of Art moved from the East End to downtown, specifically to the Housatonic Community-Technical College that also moved into the downtown, there was some fussing — as happens every time an institution moves. The college moved into a former shopping mall. In this way, you could say that Bridgeport was ahead of its time in rethinking behemoths of capitalism.

Hilariously, in a 1993 New York Times piece, pre-move, a criminal justice major at the college was quoted as being against it, saying that the former mall site was unsafe.

For those more attuned to Greater Hartford goings on, we saw that same thing when Capital Community College moved from the Asylum Hill/West End border into the former G. Fox building and then more recently when UConn left its sprawling West Hartford campus for the former Hartford Times building, both in downtown. Both times, there were students and staff who dragged their feet on change – largely because of their windshield bias-induced anxiety over parking – only for things to turn out fine, actually.

I was excited about the prospect of visiting the Housatonic Museum of Art, a 10-minute walk from the train station.

It’s free and open to the public — except for when it’s not, which is on Saturdays and Sundays.

I’m sympathetic. They have an exceptionally small museum staff. Like, two whole people. And they did find the funding so they could digitize nearly their entire collection, making it viewable to everyone, 24/7 and free, online. That’s a massive undertaking; if anyone is unfamiliar with the process of digitizing museum objects, buy me a coffee and I’ll explain it to you. This is not a task one simply pushes onto interns. It opens up so much access to collection materials. A huge round of applause to them for doing this.

But, a photograph of a painting is not the same as seeing that painting and all its texture in person. Someone, find funding for this museum so they can double their staff and open on at least one day of the weekend!

Going through downtown, I wondered about the impact of a museum being closed on the weekend, of all these feedback loops. Without a museum open, what other nearby businesses, like cafes and restaurants, struggle or fail to exist at all? It looks like the college is only offering one weekend course this coming Fall semester. The Bridgeport Public Library’s main location is closed on Sundays. With the college, museum, and library closed on Sundays, one whole block is deactivated one day of the week.

Then, also nearby, there are banks, law firms, government buildings. The Barnum Museum has been closed since 2010, though there are plans to reopen, someday. It was damaged by a tornado and repairs are taking forever.

It’s not that there’s nothing in downtown Bridgeport, but between these places closed temporarily, on Sundays, and then establishments that don’t open until afternoon, it feels unsettling to walk through on a Sunday morning. Once I was one block from the train station, there were very few people out and about, and both times I did not encounter any feminine-presenting people again until I reached The Hollow.

What does one do, then, if there isn’t much in the way of parks or anything open?

You can meander the streets enjoying something that Bridgeport has absolutely nailed: public art.

What I like about Bridgeport’s approach to public art is that they have a good variety of artists and subjects, so you don’t have like one muralist painting his girlfriend over and over again as a subject.

So, let’s start again. Scroll back up to the top of this post and take another look at the artwork, which starts where my trip ended: inside the train station.

There are paintings on buildings. Drawings turned into prints and mounted on buildings. There are painted electrical boxes. One of my favorites was the fireplace with pigeons next to the building painted to look like maybe a castle, with an existing boring steel (I’m guessing) door made to look like wood and iron.

The benches are painted.

So is the flight of stairs leading from Broad and Elm to Golden Hill Street. The impact was that I went out of my way to climb, rather than avoid, stairs, for a change.

Baldwin Plaza has brightly painted sculptures.

This is a space that would have struck me as a nothing pocket park, but the colorful benches lured me in.

Streets, sidewalks, board up windows: painted. You can spend some time just looking up and down, down alleyways, and everywhere else to see what commissioned and uncommissioned artworks are around.

If you want to organize your search for public art and find out who the artists are, you can look at the resources provided by Colorful Bridgeport — but I’ll warn you, there’s even more that they don’t have listed. (But shout out to them because in their “getting around” guide they have parking listed dead last. What a breath of fresh air!)

If you don’t have limits on your time or energy, I vote for exploration by chaos method. Wander in a direction you feel pulled in, and then turn down another street when so moved. Most of downtown is confined by I-95, Route 8, and the Pequonnock River, so you can just bounce around between those points if you fear getting lost.

As you walk, you’ll notice that Bridgeport still has some good bones. They didn’t demolish every last brick building.

Another cultural organization in downtown is  appointment only “due to Covid-19”, which does not bode well. I have seen cultural organizations in my area fall off people’s radar because their hours and event offerings remained extremely limited long after the vaccines became available.

In my wandering, I had the time to think about the miracle of a place just opening its doors. Some small businesses are doing it while others have not figure out a way how.

At home in Hartford, the first step was getting those coffee shops to come downtown. The next was to say, “okay, but you also actually need to have hours.” None are open as late as would make everyone happy, but residents asking for more has led to a few deciding to add Sunday hours or to stay open later than they were a few days each week.

What helped in getting those shops to even be downtown? Hartford’s downtown population increased. The new housing that haters said would remain empty very much has not.

I could not help but notice how much missed opportunity exists around the Bridgeport Transit Center. It’s kind of amazing how slow most municipalities in the region have been when it comes to transit-oriented development — but especially here, where the transit in question provides frequent service to both New York and New Haven.

There are some new housing projects in the works, several of which have been delayed by about five years. Those incoming residents are going to want a little more to do than what is currently being offered, and those who have more choice about where to live are going to want to know why specifically this is where they should be paying rent. Another feedback loop.

Despite the borderline creepy atmosphere of downtown before noon on the weekend, I would suggest this as a place to check out over some of the wealthier options along the shore. Support the small businesses and cultural organizations that dare take the risk of existing in and outside of downtown.

Getting There: The Bridgeport Station on Water Street.

Bridgeport uses GBT for its bus service; to travel from the train station to The Hollow, you can take the #8 bus rather than walk.