With long lines at restaurants, crowds of tourists and parking hard to come by, the Old Port can be a tough place to get into.

A few decades ago, it had a reputation as simply a tough place, one most people were in no hurry to visit.

“There were abandoned buildings, dirty streets and a rough crowd,” said Joseph Loughlin, who started as a Portland police officer in 1981 and retired in 2010 as assistant chief. “My training officer would point out a place and tell me, ‘That bar will never call the police,’ or ‘They’ll only call if there’s a stabbing or somebody gets a bottle in the face.'”

Portland’s historic waterfront district has made a stunning transformation over the past 50 years. In the 1970s, it was rife with abandoned storefronts, decaying wharves and little-used warehouses, but by the 1990s, it had become filled with local stores, restaurants and nightspots. Today, it’s home to high-end boutiques, a nationally acclaimed dining scene and nearly a dozen hotels. It attracts tourists from all over the country.

A block on Middle Street that housed a video rental store and a local record shop until a few years ago is now home to national retailers of yoga wear and home decor. A late-night pizza joint on Commercial Street was replaced last year by the popular Holy Donut, which relocated to accommodate growing lines of foodies from out of town posting photos of the brightly glazed pastries on Instagram. A cleaning company and insurance offices on a couple of blocks of Commercial Street have been replaced in the last decade by high-end furniture stores and a glassware retailer.

A view of Commercial Street on the waterfront in the Old Port around 1990, before becoming the spiffed-up tourist destination it is today. Photo courtesy of the Historic Preservation Office, Portland Department of Planning and Urban Development

Hotels have sprouted up where parking lots and a lumber yard once stood. Only one hotel existed within the Old Port’s 12 or so blocks before 2002. Now, there are 11, two of which opened last year. Rooms book upward of $500 a night on summer weekends – but can dip to $200 or lower in winter – with guests taking in the charm of the walkable area’s brick buildings and working waterfront between reservations at restaurants. Rising occupancy rates show that demand for hotel rooms continues to grow despite all the new construction.


For all the Old Port’s economic vitality and spiffy appearance, some people still avoid the area, but for different reasons than before. Some locals feel priced out by the restaurants and shops or find parking and crowds of tourists too daunting to deal with.

“I avoid that area like the plague in the summer. I don’t go after Memorial Day or before October, after the leaf-peepers are gone,” said Margaret Carignan, 59, of Portland. “Back in the ’80s and ’90s, it felt more like a tight-knit community down there.”

But other locals welcome the vibrant restaurant and shopping scene, appreciate the longtime establishments that remain and have made peace with the crowds and the parking, even in summer when tourists take over.

“The tourists don’t bother me. I know tourism helps pump money into the local economy,” said Rusty Cohle, 52, a Portland restaurant worker, as he sipped a beer in late June on the patio at Dock Fore, his Old Port bar of choice. “You just have to bide your time and deal with the madness for a couple months (in the summer). I think that’s a fair trade-off.”

Rusty Cohle of Portland at Dock Fore, his Old Port bar of choice. He thinks dealing with crowds and parking problems is a fair trade-off for the economic benefits of tourism. Brianna Soukup/Staff Photographer


The Old Port’s evolution was powered by a combination of factors, including the charm of more than 100 well-preserved or restored 19th century buildings, a picturesque waterfront location, a handful of entrepreneurs who saw the area’s potential to draw businesses and people when few others did, and the rise of foodie culture and tourism.


“I think what has been driving this is that the retail experience in the Old Port really can’t be replicated anywhere else,” said Peter Harrington of Malone Commercial Brokers, who has been leasing Old Port properties since the early 1990s. “It’s a great place to walk around, has great food and bars, whale watches and cruises. That vibrancy attracts more businesses and more people.”

The Old Port has followed the path of other historic areas that have evolved, over time, from their origins as centers of commerce and trade to walkable shopping and dining districts. But unlike other tourist destinations and waterfront cities on the East Coast, the Old Port has retained an authenticity that makes it unique, said Tracy Michaud, an assistant professor of tourism and hospitality at the Muskie School of Public Service at the University of Southern Maine.

Visitors to the Old Port can still see fishing boats and other elements of the working waterfront that fueled its creation. It’s one of few places where the tourist and working areas reside within a few feet of each other, Michaud said.

Sightseers stand on the deck of the Odyssey Whale Watch boat as they pull back into the Portland Harbor in June. Brianna Soukup/Staff Photographer

Geographically, the Old Port is a small area, stretching 10 or 12 blocks along Commercial Street on Portland Harbor, then climbing up the hill from the water, where it abuts the city’s arts district and City Hall. It’s roughly bound by Center, Franklin, Commercial and Federal streets, but in recent years has spread as new businesses and developments pop up on the fringes.

It first became an area dedicated to fishing and seafaring commerce after the British destroyed Portland (then called Falmouth) with incendiary cannonballs during the Revolutionary War in 1775, said Earle G. Shettleworth Jr., Maine’s state historian. By the 1820s, there was a thriving mix of warehouses, stores and commercial buildings, as well as hotels. What is now Commercial Street didn’t exist until part of the harbor was filled in during the 1850s, so the land met the ocean at Fore Street.

Portland’s Great Fire of 1866 destroyed a swath of buildings across the city, but left structures standing on the water side of Fore Street and much of Commercial Street. The fire did destroy many buildings on Exchange and Middle streets, higher up the hill. More than half of the 150 properties in the city’s Waterfront (Old Port) Historic District were built after the fire, which is why so many look Victorian in architectural style.


The area continued to operate as a commercial center with cargo ships, fishing, freight trains and related businesses until after World War II, in the 1940s, said Shettleworth. Then as cargo was increasingly moved by trucks and planes instead of ships and trains, it began to change. By the 1960s and ’70s, many of the small businesses that catered to walk-in customers and offered utilitarian services were moving to suburban shopping centers with parking lots. A 1972 photo of lower Exchange Street that ran in the Portland Press Herald shows signs for The Seavey Company, offering printing and binding services; Bragdon’s, a store selling paint, wallpaper and janitorial supplies; and Higgins’ Office Products.

In the ’60s and early ’70s, two men regarded as pioneers of the Old Port’s revival, who have since died, began buying buildings there and breathing new life into them, eventually attracting the attention of other developers, landlords and entrepreneurs. One was Henry Willette, a Portland city planner, who bought his first Old Port building, at 9 Exchange St., around 1967 and started a business called The Candle Shop, which went on to sell candles nationally. Another was Boston native Frank G. Akers, who first saw the Old Port’s potential while visiting in the 1950s, and began buying buildings and installing tenants around 1970.

Children run down the sidewalk near 39 Exchange St., in the heart of the Old Port, in this 1972 newspaper photo. Portland Press Herald photo courtesy Portland Public Library Special Collections and Archives

The buildings then were cheap. At one point, Akers owned 14 Old Port buildings with a combined mortgage of $100,000, he told the Press Herald in 1999. He rented storefronts to artists and craftspeople at low rates – sometimes $50 a month – and installed lights on upper floors to make the buildings seem more fully occupied.

In 2021, Old Port lease rates ranged from $25 to $55 a square foot, depending on the street, compared to an average of about $20 for the rest of Greater Portland, according to Harrington from Malone Commercial Brokers.

Tony DiMillo ran a restaurant in the 1960s and ’70s on the inland side of Commercial Street, where artisanal accessories store Sea Bags is today, and began buying nearby properties. He believed the waterfront would begin drawing people and new businesses, said his son, Steve DiMillo.

In the late 1970s, the elder DiMillo sold his buildings on Commercial Street to buy the then-crumbling and dilapidated Long Wharf, for about $650,000. He spent another $1.5 million for site improvements and a decommissioned ferry boat and, in 1982, opened DiMillo’s On The Water, a restaurant in the ferry at the end of the wharf and now a Portland landmark. Today, the four main parcels that make up Long Wharf are valued at more than $6 million.


The fear of urban renewal – the bulldozing of old buildings in the 1960s to make way for new roads and developments – spurred preservationists and others to push for having the Old Port designated as a National Register Historic District, which was in effect by the mid-1970s and offered tax incentives to people who wanted to rehab buildings. Later, around 1990, the area became part of the Portland Waterfront Historic District. Both designations have helped the Old Port retain its historic character and charm over the years.

Steve DiMillo in front of the spot on Commercial Street where his father had a restaurant in the 1960s. Brianna Soukup/Staff Photographer


By the mid-1990s, the Old Port’s reputation as a pleasant place to shop and hang out was solidified. Old buildings were protected and had been refurbished and cleaned up. Businesses like the independent theater Movies on Exchange Street, Java Joe’s coffeehouse, movie rental store Videoport, Bull Moose record shop and Casablanca Comics attracted loyal local followings. People could grab cheap eats at places like Granny’s Burritos and the Old Port Sandwich Shop.

Chris Godin, who started Granny’s in 1995 on Market Street and after moving to different locations closed for good in 2017, saw his “blue-collar” customer base erode over the years. He said the recession in the late 2000s affected a lot of his customers and, in turn, his business. He noticed that businesses like his were being replaced by pricier restaurants and shops, frequented by people who could still afford to go out to eat even if they were paying $1 more for a gallon of gas or several hundred dollars more on their rent or mortgage.

“I think that’s the biggest single difference down there now, it’s moved away from affordable places for blue-collar people,” said Godin, 58, who lives in Portland but only goes to the Old Port occasionally to hear free music at bars. “It’s gotten prohibitively expensive.”

In the 1990s and early 2000s, fights and violence in the Old Port, including stabbings and shootings, drew headlines. In 1995, the City Council placed a six-month moratorium on new bars in the Old Port, after a spate of fights and public drunkenness. Officials later considered raising the licensing fees for bars, to help pay for the added police presence.


In the late ’90s, street and motorcycle gangs started congregating and clashing, said interim Assistant Chief Bob Martin of Portland Police, who has been with the department since 1986. In 2002, police told the Press Herald that there was an escalating conflict involving several motorcycle clubs and later that they had confiscated at least 10 guns from gang members in the Old Port.

The gang presence has faded, and Martin says the Old Port is “perfectly safe” until later in the evenings, usually after midnight. That’s when the crowds transition from tourists and restaurant-goers to bar patrons, he said. There still are incidents of bar-related violence, though mostly after midnight on weekends among locals. On weekends, Fore Street closes to vehicles to give the crowds more room to disperse at closing time in an effort to prevent confrontations.

“Anytime you have that many bars in a small area, you’ll be dealing with fights,” Martin said.

People walk down Wharf Street in the Old Port in late June. Brianna Soukup/Staff Photographer


Neither the city nor tourism groups track the number of visitors who come to Portland each year, but the rise is evident in tax reports that show lodging sales in Portland grew from $56.8 million in 2007 to $111 million last year, a 32 percent increase when adjusted for inflation.

Or you could just count the number of new hotels. At least 10 have been built within or very near the Old Port since 2002, according to data from the tourism promotion organization Visit Portland. That includes two that opened last year, the Canopy Portland Waterfront and Aloft Portland, both on Commercial Street across from the waterfront. Before 2002, there was only one hotel in the Old Port proper – the Portland Regency on Milk Street – and two nearby, the Westin Harborview on High Street (formerly the Eastland) and the Holiday Inn by the Bay on Spring Street.


The Regency, a 95-room hotel that opened in 1987 in a historic armory building, has seen an increase over the last decade or so in guests from outside New England, and more recently from the West Coast, as well as in bookings for “shoulder season” months like October and November, said David Davis, its director of sales. Thirty years ago, the majority of guests were from the Northeast, and the hotel was much more reliant on business travelers.

“In the ’80s, we didn’t have the food tourism and the breweries,” said Davis. “It’s really morphed for us from the business traveler into the people drawn by the restaurants and people coming here to do a variety of things.”

Even though 10 new hotels have opened within walking distance in the past 20 years, the Regency’s business has not declined, Davis said. In fact, average hotel occupancy rates in the Portland area have increased, from 59 percent in 2012 – when the Old Port had five hotels – to 67 percent in 2021, according to data compiled by STR, a hospitality research firm.

Madison Miller, 19, pets Gerry Scott’s horse, Hercules, in Boothby Square in the Old Port late June. Miller, who is from New Jersey, traveled to Maine for the first time with a group of friends. Brianna Soukup/Staff Photographer

The Portland occupancy rate did drop to 45.2 percent in 2020, the first year of the pandemic, but the city has had the greatest recovery from the pandemic among 166 U.S. markets rated by STR. By April of this year, Portland’s occupancy rate was more than 122 percent of what it was in April 2019.

Portland also is attracting more overnight visitors during winter, which it rarely did 20 years ago. The December occupancy rate for Cumberland County hotels was 42 percent in 2014, compared to 59 percent last year, according to STR. For February, the rate has jumped from 46 to 61 percent in that time.

As tourism in the Old Port has grown, so has concern about the future of the working waterfront and preserving it as a crucial part of the area’s identity. Fishermen and city officials praised the announcement in November that historic Union Wharf was being sold to the nearby Gulf of Maine Research Institute, to be used by fishermen, oil spill responders, lobster wholesalers and other maritime businesses. Around the same time, Custom House Wharf, which had been listed for $11 million, was also sold, though the new owner was not identified.


Luke Holden, 38, a third-generation lobsterman and owner of the restaurant Luke’s Lobster on Portland Pier, says he thinks the working waterfront and access to it is critical to the Old Port’s appeal and economic success, now and in the future.

Holden grew up in Cape Elizabeth and, after college, moved to New York City to work in investment banking. He started selling lobster rolls as “a passion project” and found people there were hungry for them. So he left banking to sell lobster rolls full-time, which he says, if done right, is like “exporting the Maine experience” to customers. He spent almost a decade in New York City before moving back to Maine in 2015.

Luke’s Lobster had about 40 eateries around the world when, in 2019, Holden opened a location on Portland Pier on Commercial Street in the Old Port, next to a lobster wholesaling and distribution facility his company bought. Holden said the reason he decided on a Portland location, after opening so many others, was the opportunity to contribute to the preservation of the working waterfront that abuts the Old Port and the city’s maritime heritage.

Patrons sit outside of Dock Fore in the Old Port. Brianna Soukup/Staff Photographer

Holden says profits from the restaurant, which draws a lot of locals who bring their out-of-town guests, are crucial to supporting the lobster wholesaling facility and keeping the pier open to fishermen.

“Tourists help pay for the working waterfront,” said Holden. “I think the waterfront is what drives the special nature of this place, and all the other businesses benefit from that.”



Jim Brady, whose Fathom Companies developed both the Canopy Portland Waterfront and the Press Hotel at the top of the Old Port in the former Press Herald newspaper building, thinks the city’s restaurant scene may be the most critical component of the Old Port’s ability to draw people. Fathom Companies also manages several restaurants and bars as part of its Old Port hotels, including Union, Inkwell Lobby Bar, Salt Yard and Luna Rooftop Bar.

Brady, 59, said having renowned restaurants in a well-preserved historic district on the ocean makes the area attractive to tourists, and tourists who really want to experience an area’s food, shopping and waterfront want to stay there for more than a day.

By the mid-2000s, Portland’s restaurant scene was starting to get national attention. Portland chefs started winning prestigious James Beard Awards, beginning with Sam Hayward of Fore Street in 2004. National food and travel magazines were putting Portland restaurants on “best of” lists. Bon Appetit called Portland America’s Foodiest Small Town in 2009 and, then in 2018, named it Restaurant City of the Year. After that last honor, food tourists began turning up in droves.

Shaun McCarthy says 20 years ago he might have gotten a tourist “here and there” at Dock Fore, the Fore Street restaurant and bar that he took over in 1984. But, in addition to the spot’s strong local following, tourism is a much bigger part of his business now, and he regularly checks the hotel booking app Hotel Tonight to figure out if he needs to order extra liquor and food for an incoming wave of tourists.

“Since all the hotels have popped up (in the Old Port) in the last 10 years, we definitely see more tourists. There are always people who aren’t going to want to eat at the hotel and want to go out and find a local place,” McCarthy said.

From left, Gerard P. Conley, Joe Reali and Harry Loring chat with Dock Fore owner Shaun McCarthy in the Old Port establishment. The three said they have been coming to the bar for about as long as it has been open. Brianna Soukup/Staff Photographer

Casey Prentice, whose Prentice Organization runs several area restaurants, says not all visitors to the Old Port nowadays are overnight tourists or travelers from far away. On any given night, about a third of the reservations at his group’s Evo Kitchen + Bar on Fore Street are from the 617 area code, in eastern Massachusetts. Prentice figures it’s quicker and easier for people who live north of Boston to get to a fine-dining establishment in Portland than in Boston proper.


This month, his group opened a new restaurant on Thames Street called Twelve, which Vogue magazine named one of the country’s most anticipated openings of the year. Prentice said he is not worried about Portland’s restaurant scene being overcrowded, but he does want to pay close attention to locals and not cater solely to tourists.

“Tourism is one of the largest economic drivers this state has. But locals have to come first,” said Prentice. “They’re here seven nights a week. Delivering for them is critically important to your business.”

David Turin, who opened his David’s restaurant initially on Middle Street in 1992, said the city’s growing reputation and popularity has some downsides, including making it a more expensive place for chef-owners to start their own businesses and unaffordable for restaurant workers to live.

“When I came here, there was available space I could afford and landlords were eager to fill vacant spaces,” said Turin, 64, who runs David’s Restaurant now in Monument Square and David’s 388 in South Portland. “But it’s sad for me to hear the woes of my employees who want to buy a house.”

As Portland has become a more desirable a place to live – especially during the pandemic and with more people working from home – housing prices have skyrocketed and more high-end restaurants and businesses have followed. In Cumberland County, the median home price was $510,000 for the three-month period ending May 31, up 18 percent from a year earlier, according to the Maine Association of Realtors. The median U.S. single-family home sales price in May was $414,200, a 15 percent increase from the previous year.

Patrons dine outside on the raised patio at Via Vecchia in the Old Port in June. Brianna Soukup/Staff Photographer



For the longer view, look to the block at the corner of Middle and Pearl streets, built in 1876 for shipbuilder John E. Donnell. Tim Soley bought the property in 1993 for $1.2 million, and today its taxable value is more than $7.3 million, according to Portland assessor’s records.

In the 1990s, that block was home to several iconic Portland businesses with loyal local followings. They included the movie rental store Videoport, the Portland location of Maine record store chain Bull Moose, Casablanca Comics and Anthony’s Italian Kitchen. Videoport closed in 2015, after streaming killed the video rental business, and Bull Moose closed its location in November 2020, citing a decrease in foot traffic and an expiring lease.

Anthony’s and Casablanca Comics are still there, along with national retailers Athleta and Anthropologie, which mainly sell women’s clothes. Other prominent national retailers now in the Old Port, where there weren’t many 25 years ago, include Urban Outfitters and West Elm.

Soley, whose East Brown Cow and affiliated property management companies own 16 Old Port properties, says he’s consistently tried to fill the ground floors of his buildings with businesses that generate foot traffic. He says the hotel boom has helped bring in customers for a wide variety of businesses, because they are in the Old Port all day and overnight, unlike cruise ship passengers or day trippers. Soley also thinks the Old Port’s current mix of shops, restaurants and other amenities helps make the city a more attractive place to live and work, as evidenced by large companies like payment-processing technology firm Wex and financial services firm Sun Life U.S. recently relocating their headquarters there.

But it’s because of out-of-town visitors, and the dollars they spend, that Portland has the retailers, restaurants and cultural amenities that a city its size – 66,000 within the city limits and about 500,000 in the metro area – wouldn’t normally have, said Lynn Tillotson, president and chief executive officer of Visit Portland.

“People come for the restaurants, the shops and the art galleries, that’s why we have hotels,” said Tillotson. “Tourism is all about bringing business in and keeping the area vibrant.”


At Suger, a plant-based clothing maker with a store on Commercial Street, owner Roxie Suger estimated that about 70 percent of the store’s customers were out-of-state visitors and about 30 percent were locals this summer. During the winter months, the split is about 50-50. Suger, who also has a store in Biddeford and sells online, said she opened the Portland store a few years ago to get her designs “more exposure.” The spot is next door to the Canopy Hilton Waterfront hotel, which opened last year.

At Evangeline Linens on Fore Street, owner Ben Ray estimates that 80 percent of the people who visit the store between June and October are from out of state. Ray, a native Mainer who began the business out of his Portland home, says the majority of his sales are wholesale and online. The store functions as a showroom and a creative workspace.

Rick Lowell, who owns Casablanca Comics with his wife, Laura O’Meara, grew up in North Yarmouth and came to the Old Port as a young man. He remembers record stores and bars that are no longer around. But he also remembers it feeling desolate in spots and never, ever crowded. There are lots of tourists now, but tourists buy lots of stuff, he says.

“Tourism is a big part of our business. We still have a very dedicated local following, then the tourism sales on top of that,” said Lowell, 59, whose comics store has been on Middle Street since 1995. “Nostalgically, there are things I miss, but given the choice, I’d take what it is now. It’s so much more inviting.”

Co-owner of Casablanca Comics, Rick Lowell, in his shop at 151 Middle St. The store has been there since 1995. (Lowell was wearing a mask but took it off for the photo.) Brianna Soukup/Staff Photographer


On a Tuesday afternoon in late June, the Old Port was nearly in full-summer mode. A group of nurses from New Hampshire strolled through Boothby Square between lunch at Central Provisions and a dinner reservation at Scales. A group of young women from New Jersey, celebrating a friend’s birthday, had just come out of the Siempre Mas clothing store on Fore Street with several shopping bags. A family from Pennsylvania was taking a break from sightseeing at a picnic table near the corner of Moulton and Wharf streets.


Jen Smith had come to Portland for work five years ago and had been talking about bringing her family – husband T.J. and sons Jovian, 14, and Deklan, 8 – for vacation ever since. She said the highlights of the trip so far had been their time on the Lucky Catch lobster boat and visiting Portland Head Light in Cape Elizabeth.

“I just thought it was the cutest town, and the lobster was fantastic. We don’t get good seafood in Pittsburgh. So I really wanted to come here on vacation,” said Smith, who lives in Bethel Park, Pennsylvania.

Silas Chappell and Sara Dappolonia, both 22 and from Yarmouth, were sitting on a bench in Boothby Square. They’re both working in the Old Port this summer and enjoy coming into the district on weekend nights for the bars and nightlife.

Chappell works at Via Vecchia, a restaurant on Dana Street, and says he sees lots of people he knows, other young locals, come in on weekend nights. Although parking is hard to come by – Chappell says he often tries to get rides in or plans on giving himself at least 15 minutes to find a spot – both he and Dappolonia feel it’s worth it, considering all the Old Port has to offer.

“To be able to get out of your town and be able to go to the city, but not really a city, is really nice,” Dappolonia said.

Sara Dappolonia and Silas Chappell, both of Yarmouth, chat on a bench on Fore Street in the Old Port in June. Brianna Soukup/Staff Photographer

David Kuchta, 62, of Portland says he used to look forward to a time after Labor Day when he could “have my city back.” He could drive into the Old Port, find a parking spot with relative ease and visit shops and restaurants without fighting the crowds.


When Kuchta was shopping at LeRoux Kitchen on Commercial Street last fall, he realized this was no longer the case. Tourists are more of a year-round presence, and he has to spend more time looking for parking. He usually ends up walking further from the spot to his favorite stores than he used to.

The number of parking spots in the Old Port, including in garages, has increased by about 1,000, or 6 percent, in the last 35 years, not exactly keeping pace with the commercial development and tourist boom.

But Kuchta, who writes for an environmental website and has lived in Portland for 20 years, says he’ll keep visiting the Old Port. Dealing with tourists and tough-to-find parking, he says, seems like a fair trade-off for what the area has become.

“Even five years ago, I think there weren’t nearly as many tourists in November,” Kuchta said. “So now I have to park further away. But that’s OK, I’d rather have a vital city.”

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