Your guide to the Tipsy Triangle: A night out at Santa Rosa's favorite dive bars

The nickname of three bars at the intersection of College and Mendocino avenues in Santa Rosa depends on who you ask.

Some Santa Rosa residents might call the 440 Club, Gary's at the Belvedere and The Dirty (formerly Round Robin) the “Tipsy Triangle.” Local bar owners also have heard the “Golden Triangle” and “Barmuda Triangle.”

Regardless of their nicknames, the three bars have been a staple of Santa Rosa's nightlife since they opened decades ago. There's no preferred order for which bar to call on first for a beer, but a Triangle barhop wouldn't be complete without the full round.

If you haven't frequented these local dives in awhile, here's a look from a recent Friday night.

The 440 Club

Enya's “Sail Away” is blaring through the 440 Club's speakers. But the dive bar's odd choice of music doesn't seem to faze three women dancing in the center of the room.

The bartender laughs and swears at another man for playing the song on the 440's old-school jukebox. Between pouring drinks and making small talk, he's eating minestrone soup his girlfriend made him.

The random music selection is the only thing about the 440 Club that isn't typical dive bar. The rest is straight-up barroom. The lights are dim, the walls are plastered with Budweiser and Coors signs and a rerun of a 49ers game plays on the TV.

“We're a little dive bar, and I don't take offense to that at all,” co-owner Debbie Caron said. “I think it's neat and unique.”

At about 9 p.m., a few people are hanging around the parking lot to smoke. Regulars post up at the bar to joke with the bartender while college-aged groups of people, mostly women, wander in for a drink or two.

Most people order beer, but the bartender doesn't seem bothered when a group of young women ask for an orange-colored fruity drink.

As 10 p.m. nears, the regulars filter out and college students crowd in.

The 440 Club is named after the address of the house demolished to build the bar, Caron said. Her father bought it in 1990 and left the bar to his three daughters when he died. Now Caron and her husband, John, oversee its day-to-day operations.

Besides replacing the dance floor with carpeting and canceling the poker games upstairs, Caron said the bar hasn't changed since 1964.

“If I wanted to change something here, I'd have problems 'cause everybody loves the way it is.”

The Dirty

People are standing outside The Dirty, formerly the Round Robin, sometime after 10 p.m. but the throng is too disorganized to tell if it's a line.

Inside, the bar is more nightclub than dive, with people devouring Jello shots and a DJ blasting hip-hop music. Green and blue laser lights project onto its black walls.

The Dirty is packed with people of all ages - some dancing and others, mostly men, standing awkwardly near the dance floor.

A younger guy walks by, saying “I miss my old s***** dive bar” to anyone who will listen. He's talking about the Round Robin, with its gritty interior, wealth of pool tables and indoor fireplace.

The bar underwent a complete makeover when Crooks Coffee co-owner Cody Brown bought it in October 2019.

Dollar bills are still attached to the ceiling above the bar. But the fireplace is gone, along with most of the pool tables. The walls have a fresh coat of paint and are covered with band posters.

Brown also plans to add pinball machines, karaoke, live music and an outdoor patio.

“It's a real old-school dive bar,” he said. “We just brought [our personality] into it.”

Gary's at the Belvedere

Compared to The Dirty and 440 Club, Gary's at the Belvedere, situated in a renovated Victorian house, is a different animal, at least on the outside.

At about 11 p.m., a security guard blocks the entrance to Gary's, but there's no line to get in.

Inside, the 1970s green carpet, wood columns and neon lighting give the bar a retro vibe. It's crowded and loud, with people playing pool, pop music and groups of women sporadically shouting “woo.” It's like a college house party that's not limited to college students.

People crowd around tables near the bar and five pool tables at the center of the room. A few sit on indoor picnic benches to watch the games and people-watch. Pool is one of the bar's main attractions, and some regulars bring their own cues, bar manager Eric Drechsel said.

A mix of college students, young couples and groups of middle-aged friends talk quietly. The variety of people is why Drechsel has stayed at the bar since he was hired as a cocktail waiter in 2000.

Drechsel isn't upset when people call Gary's at the Belvedere a dive bar, but he happens to disagree. It's not dark and dingy enough, he said.

“We're either an upper-class dive bar or something different. ... We're just a little different than what I see in my mind as a classic dive bar.”