The Happiest Hours

Drinking at a Crossroads: Neighborhood Bar Tour 2005-2006

About this series: As you may have read recently, the city of Portland is at a “crossroads.” One path leads to a “yuppie playground,” where everyone lives in a condo and considers kayaking a fun leisure activity. Down the other lies the Socialist Revolution liberal newspaper editors secretly hope for. I mean dread. We dread that.

Anyway, in at least one respect, Portland is at an important intersection. City officials will soon consider zoning changes aimed at keeping bars out of residential areas. The direction the city takes from here will have a profound effect on our cultural and social lives for years to come.

Are neighborhood bars a scourge that must be stamped out before good citizens who drink in the privacy of their own homes see their property values slip from quintuple to merely quadruple what they originally paid? Or are local pubs the key links that keep our community together and make the six months of frigid dusk at this latitude tolerable?


The Bollard is launching a special investigative series called Drinking at a Crossroads: Neighborhood Bar Tour 2005-2006. Our staff will travel — on foot or by designated driver — to neighborhood bars throughout the area and conduct in-depth research to help us answer these important questions, or at least better understand whatever the hell the regulars at these places are mumbling to themselves all day. 


This doorway may not be open –or, for that matter, a doorway – for long. (photo/Chris Busby)
This doorway may not be open –or, for that matter, a doorway – for long. (photo/Chris Busby)

The Breakaway Tavern
35 India St., Portland

A great neighborhood bar is about to be demolished, consumed by the rapidly changing neighborhood around it. 

Plans call for The Breakaway Tavern, on the corner of India and Fore streets, to be razed to make way for a five story office building, perhaps by the end of this summer. 

A welcoming place dedicated to relaxation and recreation will be torn down to erect yet another faceless monument to toil and boredom. 


The Breakaway reminds me of the basement rec rooms where so much of my teenage social life took place – only better, and without the loin-aching lust and angst. For example, in addition to two pool tables and dart boards, there’s air hockey. And even though it costs 75 cents per game, the “Stinger,” by Dynamo, has an electronic scoreboard suspended above the air rink – a feature that makes any weekend puck-pusher feel like a pro! 

The best of these basement rec rooms invariably had an old, yellowed board game or mechanical parlor “amusement” that could be dusted off and given new life (and rules) as a drinking game. The Breakaway has a classic, table-top poker-dice machine with room for four players and their beers. You put a quarter in, push a red-lit button, and the little cups beneath the table each spin five faded wooden cubes. You can keep pushing the button and spinning your cup to make new hands for about 30 seconds. (What a shame this magic machine will soon be exiled to the Island of Castoff Bar Games, stranded with the Pac-Man family, Pong and a million lost cribbage pegs.) 

The Breakaway’s also got a long, spacious side patio with plenty of tables and chairs and a water view through the wood lattice and weeds on one end. The bartenders are friendly; the beer and cocktails are cheap; the popcorn is fresh-popped and complimentary. Sox games are shown on several screens. Bill Harrison’s pen-and-ink prints share wall space with beer and sports promotional posters and a huge aerial photograph of the eastern waterfront taken from a vertiginous tilt. 

On a negative note, the CD jukebox is pre-apocalyptic, as if it’s been scavenged prior to the wrecking ball’s arrival. More than every other CD case is empty, and in between remains detritus like The Best Of Cinderella (those posers are “20th Century Masters”?) and In Time: The Best of R.E.M. 1988-2003 (also known asR.E.M.: The Bad Years).

The Doors’ last studio album, L.A. Woman, was still there, so I played “Hyacinth House” in tribute to The Breakaway’s last days.

“What are they doing in the Hyacinth House/to please the lions, this day?”

Good question, Jim. I called Breakaway owner Jim Gilbert, of Gilbert Enterprises, but he didn’t call back, and I didn’t catch him on a few recent visits. I hear the developers are offering three times the property’s assessed value. Based on the land and building’s 2006 tax assessment, that would net Gilbert Enterprises over $1.5 million. 

Gilbert bought the place for just over $266,000 in the late 1990s. Before it was The Breakaway, a regular told me it was briefly a gay club called Millennium, a phase this guy blamed for The Breakaway’s deep purple walls. Before that, it was a Mexican place called Dos Locos, and in the ‘80s and early ‘90s, it was Bruno’s, a beloved rock club much like Geno’s, but with food. People tell me Bruno’s was the place to be during the Old Port Festival – back when this fest made no pretense of being anything other than a drunken street bacchanal. 

Times certainly have changed. The regular also spoke glowingly of an after-hours dance club called the Pen and Pencil that occupied this spot pre-Bruno’s, one of many such establishments in the swinging Portland of the Ford-Carter Era. The place opened from midnight to six, he said, and you brought your own booze. If you were smart, you hauled in a cooler full of beers that would fetch an increasingly higher price as dawn approached. 

If someone tried to run a club like that today, they’d be jailed. 

The Breakaway’s eastern waterfront neighborhood, an area long characterized by family-owned bars, restaurants and retail shops, is slated to soon have its own skyline of luxury hotels, condos, and condos with hotel service. All this private development is being spurred by construction of the publicly owned Ocean Gateway cruise ship terminal. 

Granted, most major private projects planned for the area have yet to actually break ground, and several seem to be on hold. But the promise of a cruise boom is driving up property values much the same way the sunrise once caused a spike in the price of Bud cans. The Breakaway’s assessed value is estimated to jump almost 50 percent this year over last, from about $500,000 to nearly $750,000. That’s a lot of Bud. 

There’s a Neil Young lyric from “Sail Away” that’s popped into my head many times over the course of this Neighborhood Bar Tour. So I was taken aback to see it written on a dry-erase board near The Breakaway’s front door, hanging prominently on a wall that may be a pile of bricks by the fall….

See the losers in the best bars
Meet the winners in the dives
Where the people are the real stars
All the rest of their lives.

The Breakaway reminds me of the great basement rec rooms of my youth, but these days, hanging out there also brings back a half-forgotten sense of foreboding. It’s the feeling you get when you’re 16 or 17, drinking contraband booze and smoking things in one of your friends’ basements – or worse, your own – and the click of a mother’s heel resounds most unexpectedly on the slate-floored foyer above. 

That’s the moment you know you’re screwed. Enjoy The Breakaway while you can. 

— Chris Busby

The Breakaway Tavern opens daily at 3 p.m.

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