The beginning of autumn is arguably the most creative time of year. A fervor spreads as we prepare to honor things popular and anachronistic by creating costumes as sexy zombie versions of those we cherish and hate.

I felt this rustling of excitement as I repaired a pair of fishnet stockings, which tie together suggestions of sophistication and arousal. I’ll be committed to my Elizabeth Warren costume the entire week of Halloween. Mr. Harada toiled diligently as well. He will be celebrating as a very naughty, zombie Trans-Pacific Strategic Economic Partnership Agreement, complete with a suggestive representation of the Mariana Trench.

Alas, the moment of Hallow’s Ween was still a few weeks away, and we wished to be enveloped in the five muses: creativity, imagination, tradition, class and libation. Luckily for us, the five aforementioned points converge on a daily basis in San Jose at none other than Five Points, downtown San Jose’s newest craft cocktail lounge.

Mr. Harada and I mounted our tandem Big Wheel and pedaled toward Santa Clara Street and Almaden. Two miles and an hour later, we stood in front of the Five Points. In honor of the venue, and in keeping with our dedication to historical accuracy, I dressed as Daniel Day-Lewis’ infamous Gangs of New York character Bill the Butcher, while Mr. Harada modeled a faithful depiction of a cobblestone street where director Martin Scorsese once planted his camera to capture history as it happened.

Indeed, the Five Points pays tribute to the fabled meeting point of New York City’s five boroughs. The saloon is spacious, clean, refined and well thought out. While the wooden decor is splendid, achieving a rare balance between intimacy and open space, Mr. Harada and I were most delighted by the cocktail selection.

Legend has it that one of our most favored booze-smiths had a hand in defining the flavor architecture (or flachitecture, as I’m certain they say in Manhattan). As bartenders go, Syrus Fotovat is a ruthless dreamer who won’t let anything stand in the way of his ambitions. In that way he carries on the tradition that the butcherous William Poole started when the Five Points was young—a time when everyone had a dazzling mustache (yes, even babies and dogs).

Mr. Harada and I sat at the bar and scanned the cocktail menu (all $12) like 19th-century street urchins gazing through the window of a meat market. The “Paradise Square” immediately called my name. Polish bison vodka with pineapple and egg whites are ingredients for the refined drinker. As disparate as they may seem, it’s a worldly blend that satisfies completely.

Being a man of the street, Mr. Harada ordered the “Baxter Street Dude.” It did not disappoint. A bitey front with a floral, Caribbean vibe, the drink pays homage to a century of oceanic discovery, and the promise of a new era.

Drinks at Five Points are well designed, just like the space. There are few distractions outside of the people and inventive pours. The cocktail lounge is new, but it holds onto the tradition of what a bar should always aspire to be: a comfortable place for libation and conversation.

Five Points
169 West Santa Clara St
Craft Cocktails, $$