[B] Lingering Libbytown Story

The gateway to Portland searches for its identity.

By Emma Deans

Stepping off the Concord Coach Lines bus into Portland, Maine, visitors to the city are welcomed with a variety of brochures boasting of Portland’s walkable streets and high livability. Located on the outskirts of the city where the Fore River estuary cradles Portland’s peninsula to the south at Thompson’s Point, the station posts a small, rectangular sign next to its doors pointing to “Metro—Local Bus and Taxi.” No signage shows those walking or biking options downtown.

Upon exiting the station to the right, a paved sidewalk does run alongside the Fore River Parkway but problems persist. The pavement portion is not marked and the Fore River Trail, which winds alongside the river’s edge, abruptly ends. A desolate ambiance saturates the air, as a community of groundhogs scurries about large piles of crushed rock underneath an overpass and alongside train tracks. An old railway bed lines the path and several skinny, young birch trees weakly populate the area.

Libbytown serves as Portland’s transportation hub and lacks a welcoming feel. The neighborhood remains fragmented in large part because of I-295.

The panorama becomes hectic as pedestrians attempt to access the city’s downtown. Cars zoom across highways in all directions. Train whistles sound, as the Amtrak Downeaster puffs south to Boston. Planes soar overhead, racing off the runway at Portland Jetport, gaining elevation over Casco Bay.

Underneath the neon glow emanating from Denny’s diner, a large slab of concrete divides Park Ave from the state’s most notable road, Congress Street. A brown, metal sign marks the territory in yellow letters: Libbytown.

Neither here nor there, Libbytown serves as an in-between place as a result of the Urban Renewal movement of the 1960’s, which promoted modernization based upon the automobile. Ask any longtime Libbytown resident what caused the death of the neighborhood and you’ll likely hear something along the lines of, “Goddamn 295.”


Portland Trails has a vision to reconfigure the landscape to be more a more neighborhood-friendly gateway to the city. In Portland’s East End, at the Hilltop Coffee Shop, Jaime Parker pours over city maps, analyzing trail routes and municipal zones. A graduate of USM’s Muskie School of Public Service, Jaime is in his eighth year of working for the non-profit urban land trust. “We’re really about connecting communities and improving transportation options,” Jaime explains. In September of 2008, the Portland Area Comprehensive Transportation System approached Portland Trails with the task of analyzing neighborhood connectivity in Libbytown. With the consultation of Oak Engineers, a local engineering firm, Portland Trails presented the report to the city in the fall of 2009.

The area along the Fore River feels desolate in many ways.

Libbytown “really doesn’t have an identity; it doesn’t have a sense of place,” Jaime notes, lifting a mug of hot coffee. “It’s important to know that it was built at the heyday of auto dominant infrastructure and Portland really suffered. There were many benefits, of course, but I think our communities as a whole took a loss.”

The 38-year-old Trails Manager nods his head and greets several residents who walk in and out of the shop. Portland’s East End, located northeast of Libbytown, is known for its distinct bohemian vibe. Bordered by Casco Bay, the Eastern Prom serves as a recreational district, providing an extensive grassy area for picnicking, reading, Frisbee-tossing and other leisure activities. In contrast to Libbytown, Munjoy Hill has a well-established neighborhood group with its own office, a neighborhood newspaper and several community events such as backyard garden tours and fundraising road races.

While Jaime believes that many people are attracted to Portland because of its welcoming feel in areas like Munjoy Hill, for places like Libbytown, structural improvements are needed to undo some of the mistakes made by the large-scale demolition created in 1969 when the highway was built. Fifteen businesses closed. Two hundred families were forced to relocate from their homes. The chasm it left behind impacts both the physical and social wellbeing of the area.

Jaime identifies, “The primary concern is being disconnected—living in the city but not being able to access the city in an easy, safe, welcoming way.” He adds, “Through the process of writing a report on pedestrian and bicycle improvements for Libbytown, we were originally looking at a singular route connecting the Transportation Center, where the train comes from Boston and where the buses come into Portland, to Deering Oaks Park and the whole Hadlock Field area.” However, “it grew into, I think a whole series of recommendations that get at different ways to connect Libbytown to Portland proper.”

Jaime Parker stands in front of a community garden he has started in the East End. Jaime says Libbytown "really doesn't have an identity; it doesn't have a sense of place."

The Transportation Center’s location is “really troubling, to be honest,” Jaime says. “I’ve taken the bus and train many times and come into Portland…it just feels forlorn and it’s not a welcoming place.” He would not recommend someone who is unfamiliar with the city arriving on the train or bus at night. “Their first introduction to the town should not be a dark, scary, unsigned, unclear, confusing route.”

With his own, well-used skateboard resting by his side, Jaime envisions a large-scale shift from auto dependency to alternative forms of transportation in order to bring back the neighborhood cohesiveness once found in the area. “We, in many ways, sort have reached the pinnacle of our auto dependence and our auto worship…there’s a really promising trend nationally and certainly Portland has recognized that we came a little too far down the auto road and there are other things to consider when we build our cities.” Beyond logistics, “I think the quality of life piece [is] something that more and more people are placing high on their list, as far as factors to consider when they’re deciding where to live or where to work,” Jaime points out. “Community is what makes our everyday life worth living.”


Down the residential streets of Libbytown, the roar and racket of Congress muffles. On Whitney Ave, a mother leisurely unearths weeds and plants tulips on her front lawn. Around the corner from the auto repair shop, a barefoot woman wearing stretch pants and a gray T-shirt smokes a cigarette, watching as a crushed milk jug floats down Congress, repeatedly being hit by cars. On Douglass Street, a tattoo-clad man wearing a backwards, red baseball cap informs someone on his cell phone of his upcoming court date.

Tony’s Donuts is one of the last remaining places in Libbytown with a sense of community.

If there’s any sort of community gathering place left it’s at Tony’s Donuts, whose windows proudly proclaim, “Life is uncertain. Eat dessert first.” Hand-cut pastries line glass cases at the neighborhood shop on Bolton Street. Bismarcks ooze red raspberry and fluffy, white cream. Molasses, glazed and powdered doughnuts wait for eager customers who shuffle in at all hours of the day to enjoy a New England specialty: coffee, sweets and conversation.

On a quiet Friday afternoon, Fred Dillon, clad in a long-sleeved, mountain green Carhartt shirt, munches on a Tony’s pastry, “supporting local business.” Fred, who works in South Portland as a Storm Water Program Coordinator, has served as a representative for the Libbytown Neighborhood Association, which used to meet at Tony’s to discuss problems and potential improvements for the area. A Libbytown resident of 17 years, Fred comments, “A group of us started to get together to go through the not very glamorous part of developing bylaws and actually getting organization. We met with other neighborhood groups to learn what they were doing and [we got] a lot of help from them.” The group received media coverage and rallied quite a bit of interest, but around four or five years ago the discussions dwindled. “It became a question of just a few of us doing the work and people kind of tailing off on meeting attendance.”

Father to twin 11-year-old daughters, Fred grew up on Gilman Street, just beyond Libbytown’s border of Saint John Street. He expresses disappointment with Libbytown’s infrastructure and comments, “It just looks like a miracle mile you would see anywhere.”

Locals and out-of-towners visit Tony’s Donuts for hand-cut pastries and good conversation. The shop, full of character, has been open since 1965.

Surrounded by gas stations, hotels and convenience stores, Tony’s Donuts represents a slice of the blue-collar Libbytown identity still living today. Patrons dressed in sweatshirts, jeans and sneakers gather to read the paper, discuss sports and banter about local and national news. Discussions range from Tiger Woods, “He can choose any girl in the country; I just want to see him play golf,” to politics, “They gotta put an age limit on the Supreme Court,” to culture, “Those Frenchmen—they’re always half-naked anyways.” A number of Yankee Caps clash with Red Sox fans, making for comments like, “Go ahead, dump on my Yankees. At least we’re not one-and-three.”

The current owner of Tony’s, Rick Fournier, emphasizes a business model based on friendly service. Rick’s father established the doughnut shop in 1965 at a time when they “were just a small guy, just struggling along and then it started taking off about ten years ago,” Rick says. While Dunkin Donuts, Tim Hortons and Starbucks chains have sprung up, he hesitates to call it “competition, per say, cause you know, there’s plenty of business for everybody.” Rick, who also serves as a pitching coach for South Portland’s softball team, emphasizes, “My father used to do it, now I do it and my daughters do it—it’s about talking to the customers. Your customers become your friends and that’s the biggest part—making new friends.”

Tony’s location just off of Congress Street is convenient for commuters and out-of-towners but Congress, Fred explains, “is one of the main arteries into the city.” Speeds are posted at 35 miles per hour and cars often race in at much faster rates, discouraging bikers and pedestrians. Fred rides bikes with his daughters but notes, “I don’t let them ride by themselves because it’s scary.”

It’s a problem that’s manifested in the fragmentation of community interactions. Fred remembers when he first moved to Libbytown’s Davis Street, “I was really excited about Halloween ‘cause I like kids…and we’d get no one. Literally no one would show up ‘cause [the kids] won’t cross Congress.”


While the construction of I-295 felt like the death of Libbytown to many residents, others remember the demolition of Union Station on Saint John Street as the beginning of the end. The railroad, which opened on June 25, 1888, was destroyed on August 31, 1961. In response to Union Station’s destruction, community members founded the Greater Portland Landmarks organization in 1964 to preserve and protect historic places in the area.

Union Station was demolished in 1961, spurring a preservation movement in Portland. The railroad was a major landmark and its loss was devastating for the area. | Photo courtesy of Greater Portland Landmarks.

Still, a strip shopping mall with the discount box store Arlans sprouted up where the Station’s trains used to rattle into town. Today, the old tracks run behind a shopping center that includes a Save-A-Lot, Dollar Tree, Rent-A-Center and chain Chinese restaurant.

An article from the 1974 edition of the Portland Evening Express cites Myles Anderson as the unofficial “mayor” of the neighborhood. Then age 67, Myles explained that the area was originally dominated by Irish Catholics, who designated it Libbytown, rather than Libby’s Corner, its official name. “The named Libbytown had a warmth about it that the Irish never found in Libby’s Corner. Besides, the Irish don’t like to be cornered under any circumstances,” Anderson told the Express.

The Libby family emigrated from Ireland during the mid-nineteenth century and owned three businesses on Libby’s Corner between Park Ave and Congress Street: a tavern, blacksmith shop and paint store. There were 17 Libby families registered in the area during the 1850s, which grew to 100 families by 1889.

The Portland Trails report explains, “If there is a ‘center’ of Libbytown today, it may be the intersection of Congress and Bolton Streets, defined by Anania’s Market, Tony’s Donuts and the Mobil Mart, though the area has more of a ‘suburban strip’ feeling than a village center.”

Dougherty Field, home to a collection of baseball diamonds on Douglass Street, has the potential to serve as a community center. It’s situated behind West School, which provides adult education programming and serves students with behavioral and learning disabilities. A master plan is in the works to revamp the open green space and make it more of a destination for recreational purposes.

Libbytown's baseball fields could become a community gathering place. A skate park is under construction and a master plan is in the works to utilize the green space.

On a warm, weekend afternoon, the Dougherty complex is mainly vacant. An elderly man pans the grass with a metal detector. A young woman takes a nap with her small, black dog. Kiwanis Pool, an outer swimming center located past the ball fields, sits undisturbed and void of water, waiting for summer sun. Behind Perry Field, a construction crew digs up dirt for a new skate park that will hopefully attract boarders from across the city.

Fred comments, “It’s interesting because the skate park had a lot more people concerned about it; they really didn’t think that they wanted it here ‘cause they were afraid that there would be an unsavory element that would come and kids would hang out.” Fred admits being a “scrappy city kid” and says he and his buddies “used to hang out on the baseball fields and go down in back of the railroad tracks behind Saint James Street and do the things that kids are probably still doing to this day.”

Though organized baseball leagues still draw people to this section of Libbytown, it seems to lack an atmosphere supportive of informal play. Sports talk is always on the table for Rick Fournier and his customers at Tony’s Donuts. He reminisces about Little League in Libbytown back when it boasted one of the best fields in the region (which now serves as a parking lot). Rick remembers, “We just used to have pick-up games and play each other.” Today, he laments, “You don’t see any of it. Kids just don’t go out and do pick-up games anymore and enjoy it. You know, you learn a lot of things from them ‘cause you’re making up the rules and everybody’s learning how to negotiate.”

While Fred says, “There’s no real center or heart to the neighborhood,” he also thinks, “There’s a lot of potential and I keep talking about trying to revive the neighborhood association.” In order to recover that energy, Fred says, “It either needs to be a really charismatic person (which isn’t necessarily me) and/or a catalyzing event.”


Libbytown is the first section of Portland that many visitors see upon arriving to the city.

Beyond bringing back a sense of community, Jaime Parker points out Maine’s financial dependence upon tourism as being a reason to re-think the structure of Libbytown. He comments, “There’s a huge economic development aspect to this in that we want to bring people to Portland; we want to provide a good experience when they come to [the city] and if that first impression of Portland is a train station stuck in the middle of nowhere with no clear way to get to town, that’s a problem. That’s a big problem.”

A Massachusetts native, Jaime took up jobs in carpentry, landscaping and renovations after receiving a degree in Natural Resources Planning at the University of Massachusetts at Amherst. He drove through Portland a number of times on his way to some cooperatively owned land in western Maine. Jaime explains, “With eight other folks we sort of have our back-to-the-land cabin, solar-powered and off-the-grid. In the process of constructing the cabin in the woods, we passed through Portland and it just clicked for me. I really wanted to live here and was fortunate enough to be able to move to Munjoy Hill before the real estate market went crazy.”

While images of wooded lands and winding riverbanks are usually associated with the label Trails Manager, Jaime points out the aspects of working in the city. “It’s an urban area and if you’re going to be working on trails, you’re going to be working on sidewalks and neighborhood connections,” he says. “Once you start to work on those things you start to realize the importance of that infrastructure in creating communities…the effect it has on communities and its benefits are so tangible.”

The city of Portland has made an application for funds to get the first project underway, improving the connection on Park Ave from Deering Oaks to Saint John Street and along the rail trestle. If the funds are approved, Jaime says, “I would anticipate neighborhood meetings and there would be further work to do to clearly define what [neighborhood] expectations are and what we might get out of that project.”

Potential improvements to Libbytown include making the area more friendly to pedestrians and bikers.

Other long-term goals include reestablishing Congress and Park Ave as two-way streets, identifying redundant on and off ramps for potential removal and bringing more neighborhood businesses into the area. While commuters will still use Congress to access the city, “hopefully no longer at the expense of the residents of Libbytown who suffer from a road that isn’t designed to do much more than carry very busy traffic,” Jaime says.

As for a timeline, he states, “I have to be realistic and say that if in ten years we haven’t made substantial progress, then I’d be disappointed, but I don’t expect that it will happen overnight…my hope is that the work that goes into identifying some of these barriers and obstacles and potential improvements for this part of town could serve as a model for other parts of the town and even the region.”


Walking the streets of Libbytown late at night, television and computer screens glow against the silhouettes of families in drafty, old apartment buildings. Cars are parked in a state of slumber alongside roads and in short driveways. On Congress, blinking red lights flash, as traffic slows. Unlike New York, Portland sleeps at night.

In only a few hours the sweet smell of sugar and dough will waft out across the streets, as workers begin to make hand-cut doughnuts at Tony’s. The whistles and beeps and growls of transport will resume, as commuters and visitors filter in and out of Maine’s largest city.

Dusk in Libbytown.

But in these quiet moments at night, when Libbytown is left to herself, one can almost hear the sounds of what she used to be—a place for scrappy city kids and pick-up ball games, for backyard adventures and train track wanderings. A place where houses were loud with the sounds of kids coming and going and where families actually knew one another. As fog rolls off Thompson’s Point and salt from the bay lingers among chestnut and pine trees, one can only wonder if—and when—the city can revive the spirit of Libbytown.

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