San Simón didn't get voted Bend's best bar because we voted for them (although we did) or because they're new and bohemian as hell (although they are); they were voted best bar because from the moment it opened, the staff carried themselves like they were. Not acting like it in a pretentious way or without earning it; instead, they just wanted to mix perfect and varied drinks, have service that makes you feel like family and an ambience that feels simultaneously ancient and of the moment, like a thousand-year-old church nestled in the heart of a city that can't stop growing.
"This is the kind of bar you would come in to write your novel, design a tattoo, read a book or just hang out over candlelight," says Owner Brian Trottier. Sophisticated debauchery is their mantra and seeing the hundreds of people filling the alley on a Friday or Saturday night, it's a mantra that has caught on completely. Trottier curates the tone and texture of the bar so precisely that he builds three different 11-hour music playlists every week to keep the mood vibrant and organic.
San Simón was only open five months before COVID shut it down, but upon shifting fire tables into the alley, it didn't just pivot into becoming a popular outdoor spot, it became a natural part of the landscape of Tin Pan Alley.
Trottier explains, "Everyone we worked with in the design of this place, I would say, 'I would like this place to look like it's been here a hundred years and if it's here a hundred years from now I hope it looks exactly the same.'"
San Simón was voted Bend's best bar for many reasons, but also for just one reason: When they opened, it wasn't about streamers and bells and whistles or making some garish mark upon the face of the town. They quietly opened down a dark and beautiful alley and almost instantly became a part of the downtown's living and breathing ecosystem. San Simón is Bend's best bar because, after spending just a few minutes there, you would never know there was a time when it wasn't.
Second place: Dogwood Cocktail Cabin