Bartender Madison Thibert pours a beer for a customer at Amigo's in Portland Tuesday afternoon, Jan. 3, 2023. Amigo's, opened in 1972, is the longest-running bar in the city's Old Port. Jan. 3, 2023. Credit: Troy R. Bennett / BDN

PORTLAND, Maine — Time-tested subterranean waterfront drinking establishment Old Port Tavern served its final pint of beer and closed up for good in the wee hours of New Year’s Day. Known for its topless mermaid sign and underground location in the basement of the historic Mariners Church building, the bar was 50 years old, or thereabouts.  

It opened in 1973, just as the district’s brick buildings and cobblestone streets were making a comeback with the help of city, state and federal redevelopment funds. Loyal patrons usually referred to the tavern by its initials only, calling it the OPT.

But Old Port Tavern wasn’t the longest-standing beer joint in that sea-adjacent part of town. That title is still held by Amigo’s, which opened the year before OPT, in 1972.

When the Mexican-themed watering hole served its first taco, Richard Nixon was president, the Vietnam War was still raging and the Basketball Hall of Fame had just inducted its first Black player.

Locally famous for its tiny bathrooms, pool tables and storied Wharf Street-facing patio, the bar has become a symbol of steadfast agelessness in an era of lightning-fast change in the city. It’s also a homey, wooden bar nestled amid a growing number of upscale restaurants.

“We’re a big family here,” Arlyn Vaughan said, as he sipped an after-work pint on Tuesday afternoon. “They’ve always got great bartenders here and the new chef upstairs is making some really authentic, new food.”

Just down the bar from Vaughan was Chris Webber.

“This place is definitely a staple,” Webber said. “It’s warm, friendly.”

Pictures, stickers and notices cover the wall behind the bar at Amigo's in the Old Port.
Pictures, stickers and notices cover the wall behind the bar at Amigo’s in Portland Tuesday afternoon. Amigo’s, opened in 1972, is the longest-running bar in the city’s Old Port. Credit: Troy R. Bennett / BDN

Nobody in the bar on Tuesday was old enough to remember Portland without Amigos. But Webber said he definitely first started coming when he turned 21 in 2007, and the place has always looked the same to him.

“This used to be a meat market,” bartender Madison Thibert said, “like a real meat market.”

“Totally,” Vaughan said. “This was a butcher shop before it was Amigo’s.”

It’s true — Amigo’s moved to its current home, a former meat cutting market, at 9 Dana St., in 1983, after a fire drove it out of its original spot around the corner at 193 Commercial St.

With Old Port Tavern knocked out of second place in the oldest Old Port pub standings, Dock Fore and Three Dollar Deweys are now the second-oldest bars in the Old Port.

First opened in 1980, Boothby Square’s Dock Fore remains a small, low key neighborhood-feeling establishment with a few sidewalk tables and professional soccer often on the television. A one-page Dock Fore menu from 1982 preserved at the Portland Public Library lists a burger with sauteed mushrooms and onions for $3.25 and a cup of chowder for $1.75.

Bessie Zeitman moved her combination variety store, lunch counter, lodging house, and cigar shop to the same location at 336 Fore St. in 1922. Later she operated a grocery store there, too. Her name can still be seen above Dock Fore’s door.

Opened in the same year as Dock Fore, Deweys helped usher in the era of serious craft beer drinking, serving unusual and small batch brews from the get go. In 1995, the bar moved from its original home on the corner of Fore and Union Streets to where it sits now at 241 Commercial St. The newer, bigger location had room for more than 30 beer taps.

Deweys closed suddenly in 2018 under mysterious circumstances but reopened a few months later under new management, just in time for St. Patrick’s Day 2019.

Rounding out the top three oldest suds dispensaries in the Old Port is DiMillo’s floating restaurant, which has been tied up at Long Wharf since 1982. But — even though it has what is probably the longest bar in Portland — DiMillo’s is more eatery than tavern and doesn’t really qualify for this list.

Amigo's is the longest-running bar in Portland's Old Port.
A light drizzle falls on Amigo’s in Portland Tuesday afternoon. Amigo’s, opened in 1972, is the longest-running bar in the city’s Old Port. Credit: Troy R. Bennett / BDN

In that case, the third-oldest waterfront pub in Portland would be Rosie’s, which opened its doors in 1987. The pub was started by Steve Harris and his wife — and namesake — Rose Harris. Rosie’s is located in the Davis Building at Boothby Square on Fore Street.

Other Old Port oldies include Gritty McDuff’s, opened in 1988, and The Armory’s lounge, which started serving drinks in 1989.

Looking elsewhere in the city, outside the Old Port, Amigo’s is just a pup. Forest Gardens opened at 371 Forest Ave. in 1936 and is still slinging brews. Matthew’s on Free Street claims to be Portland’s oldest pub, advertising a start date of 1872. However, that alleged date is a holdover claim from a former watering hole in the same location called Portland’s Oldest Pub, or Pop’s, and cannot be substantiated. 

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Troy R. Bennett

Troy R. Bennett is a Buxton native and longtime Portland resident whose photojournalism has appeared in media outlets all over the world.