Weekends are for amateurs. Weeknights are for pros. That's why each week Stuart Schuffman will be exploring a different San Francisco bar, giving you the lowdown on how and where to do your weeknight right.  From the most creative cocktails to the best happy hours, Stuart's taking you along on his weeknight adventures into the heart of the City's nightlife.  So, who wants a drink?

A great bar is more than just a place to drink. It’s a secondary character in stories of romance, regret, radiance, and redemption that transpire nightly throughout every town in the world. The Edinburgh Castle is one of these great bars. It’s the kind of place where, on a random night you can meet the person you end up marrying. The kind of place where you can get your heart broken by one of life’s innumerable letdowns. It’s where you go to celebrate a momentous promotion and where you go to try to drink away the passing of a dear friend. Occasionally, The Edinburgh Castle is almost as important as the person who did the thing you’re telling the story about.

We were sitting there the other night–Jon, Jeremy and I catching up on the time that slips by while you’re busy trying to figure out what being "grown-up" is all about. We’d all lived together back in college in Santa Cruz, above Café Pergalesi, the coffee shop that birthed the Devil Makes Three, and a secondary character in it’s own right. A lot had changed since those Santa Cruz salad days: Jeremy is now married, Jon toured a lot with his successful band Judgement Day, and I was living this weird, pieced-together life that I’ve managed to carve out for myself. Truthfully, we could’ve been in any bar in the city, but something about our history together, the history of the bar, and our collective history within the bar made it all fit together like something grander than it was.

Edinburgh Castle isn’t much to look at (besides its huge size and its vaguely castle looking interior), I think Herb Caen even wrote skeptically about it’s sticky floors, but that’s probably part of what makes the bar great. There’s no pretension, no snobbery, no bartenders with fancy mustaches making drinks with previously unheard-of ingredients. There’s just good beer, good scotch, and the kind of soul a place can only attain after being in business for over 50 years. There was even a time where a good portion of San Francisco’s literary scene was anchored here. In the mid 90s, writers like Irvine Welsh, Bucky Sinister, and Beth Lisick turned the place into such a haven for readings and plays that the Chronicle called it a “Literary Fortress.”  

Fifty years is a long time, and I’ve only been visiting the Castle for ten of them. But in those ten years, the dangling Scottish flag and the year-round Christmas lights that adorn the place have seen a lot of me. I’ve twice brought my yearly pub crawl to the Castle, had horrible first dates there, made out in one of the darkened corners, won the Tuesday pub quiz, and danced till I sweat through my clothes at Club 1964 – the 60s dance party that happens every other Wednesday. It’s also one of the first places someone told me they liked my work and bought me a drink because of it.

And nothing in particular happened that night other than Jon, Jeremy and I went to a concert and talked about the past and the possible future. But all that “nothing” that happened, happened at The Castle and we just added one more night to our decade-plus friendship with each other and the bar. Life goes in cycles but like a character in any story that often gets told, The Edinburgh Castle’s role just gets bigger with each telling.

950 Geary Street, 415-885-4074

Stuart Schuffman has been called "an Underground legend" by the SF Chronicle, "an SF cult hero" by the SF Bay Guardian, and "the chief of cheap" by Time Out New York. He is also the host for the IFC travel show Young, Broke & Beautiful. Follow him @BrokeAssStuart.