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    San Simon - Gin Gimlet

    San Simon

    (108 reviews)

    $$

    San Simon is a fun little hidden gem! Tucked away down an alley, it almost feels like you're…read morediscovering a secret speakeasy. The atmosphere is rustic, cozy, and a little exclusive, which made it a really unique spot to grab a drink! We stopped in right after checking into our hotel, and it was the perfect first stop to kick off our weekend. There isn't a ton of seating, but you can choose between the cozy indoor space or the patio in the alley. Since there were only two of us, we were seated right away. If you're looking for a relaxed place to enjoy a quick glass of wine or a cocktail before exploring the rest of the town, I'd definitely recommend stopping by here. It's a charming spot with great vibes!

    Follow the alley. Trust me…read more You know those places you stumble into and immediately think, "Yep...this is my kind of spot"? That was San Simón for me. At first, walking down the alley in downtown Bend, I honestly was not sure what we were about to find. Then we started seeing little fire pit pods, heated huts, glowing candles, and people tucked away having cocktails. It instantly felt cool without trying too hard. Walking into San Simón felt like stepping into some funky speakeasy hidden in plain sight. Dark lighting, moody atmosphere, David Bowie playing in the background, wild artwork on the walls that makes you stop and stare for a second. Just a great vibe all around. The kind of place where you sit down and immediately relax into the evening. The cocktails were excellent. Not overdone, not syrupy, just really balanced and well made. One of our favorites was the "Some Positive Feedback," which came with this sugar rim that looked awesome and added just enough sweetness without overpowering the drink. Bright citrus flavor, refreshing, smooth, and dangerously easy to drink. Then we asked the bartender if they could just make us something off the cuff. We said vodka, lemon and lime forward, not too sweet, maybe a little spice. They absolutely nailed it. Crisp, refreshing, layered citrus flavor with just enough heat on the back end to keep it interesting. Honestly one of those cocktails where everybody at the table takes a sip and immediately goes, "Oh wow." As a bourbon guy, I was also pleasantly surprised with the whiskey selection. The bartender recommended Stafford's Reserve, an Oregon bourbon, and I am glad I listened. Smooth, approachable, a little sweet up front with some spice on the finish. Easy sipping bourbon that fit the whole vibe of the place perfectly. What really made the night though was the staff. Everybody was friendly in that genuine way where you feel welcomed instead of "served." By the end of the night it honestly felt like we had been there before, even though it was our first visit. The outdoor setup deserves some love too. Bend cooled down at night, but the fire pits and heaters kept everything comfortable. We could have easily stayed another couple hours just hanging out. Pricing felt fair for the quality of drinks and atmosphere. This is not a dive bar pretending to be fancy. It is a genuinely cool cocktail spot that knows exactly what it is. If you are in Bend and enjoy craft cocktails, bourbon, cool music, quirky atmosphere, and places with personality, go find San Simón. Half the fun is finding it tucked down the alley in the first place.

    Bar RBC - Grilled octopus

    Bar RBC

    (38 reviews)

    In Bend 4x a year, been looking for a restaurant we want to go back to for 8 years (so many…read morerestaurants in Bend!) and tonight found the one we will return to! Best service ever (Darian) and fantastic kitchen and wonderful bar. This place is awesome, beautiful and so many things to try! The food we had tonight was stellar! Charcuterie with three good cheeses (not the pretty ones that don't taste good) but real delicious cheeses, amazing zucchini pickled, fabulous meats, bread, crackers, quince jam and more - an amazing cheese plate for only $29! Marvelous cocktails and mushroom mousse that was best ever on incredible toast points. We are excited to return! This IS the place to eat in Bend! Couple next to us said Grilled Octopus was fantastic but they ran out! It's ok - the amuse bouche olives were great too! No room for their delectable desserts - this time!

    We've celebrated three birthday dinners at Bar RBC over the last six months. I want to preface this…read moreby saying that the staff is always great. They're absolutely professional, kind and very good at their jobs. My challenge with Bar RBC is the menu. I am a near pescatarian and I have struggled to find the right things to be able to order here. I don't like their steaks or other meat items, they are of medium quality (my husbands steaks feel like they should be $20 from WF) and don't have the same high quality as their sister location up the hill. It doesn't feel right to me to pay so much for a simple shrimp skewer. I've ordered that before, but it's just not worth the cost. I just feel like the menu needs a little more depth. More veggies and more exciting things for those of us who don't love meat.

    Bend Beer Vault - partyequipmentrentals - Updated September 2026

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