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    San Simon - Aperol popsicle in cava.

    San Simon

    (107 reviews)

    $$

    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.

    The drinks are consistently great, always made with care. The atmosphere is a fun alternative vibe…read more When it gets busy, it gets busy--but that's why it's nice to visit on the slower days for even more attentive service, just like anywhere else. Thanks so much to the San Simon staff for all the wonderful experiences!

    Dear Irene - Scallops

    Dear Irene

    (89 reviews)

    From the decor and atmosphere to the unique cocktails and attentive service, Dear Irene is one of…read moreBend's best restaurants. They offer a fixed menu with great starters, salads, and entrees. We ordered the scallops which were full of buttery deliciousness, the chicken which was cooked to perfection with crunchy breading on the outside, and a creamy polenta dish. You can't go wrong but be sure to order one of the salads. Our favorite was the baratta and citrus salad with olives and pine nuts. It has all the textures and sweet-salty goodness you could want. As for cocktails, our favorite was the pear and side piece drinks. The presentation is beautiful and they really are one of a kind. We'll be back!

    I randomly stepped inside this place noticing the pretty decor and classy interior. The service was…read moreexceptional from start to finish. I was served by a tall male bartender who was incredibly personable--we talked quite a bit, and honestly, I'd go back just for that experience alone. That said, the drinks he crafted and the food that came out of the kitchen gave me plenty more reasons to return. I ended up ordering an impressive amount of food, and by the time I hit my fifth large course, he joked that he'd have to pinch himself if I actually finished it. I couldn't help it--everything was that good. He also pointed me toward the owner, who clearly knows exactly what he's doing in the kitchen and carries himself with confidence and intention. Every aspect of this place felt immersive, like stepping into a classy, well-directed film. The atmosphere, the food, the service--it all came together seamlessly.

    Broom Closet - What's behind the secret door

    Broom Closet

    (50 reviews)

    $$

    We were staying the night at McMenamins in Bend while traveling from California to Washington, and…read moreone of the highlights of our stay was hunting down the speakeasy bar, The Broom Closet. Half the fun is searching the property for it--and don't worry, I won't spoil where we found it! Once inside, it truly felt like a hidden gem. The space is cozy and intimate, with comfortable places to sit and a full bar that feels tucked away from the rest of the property. It was especially festive during the holidays, with Christmas drink specials adding to the charm. I ordered the NA Merry Cherry, which was gingery, slightly spicy, and super refreshing--a great non-alcoholic option. My wife had The Countess and said it was absolutely delicious. Between the atmosphere, the drinks, and the fun of discovering it, The Broom Closet was a total win. If you're ever staying at McMenamins Bend, make sure you take the time to search for The Broom Closet--it's well worth the adventure!

    Such a cool little addition to the Old Saint Francis hotel. We were staying at the hotel and…read moreencouraged to explore and go find the Broom Closet. Once we did find it, we enjoyed a cocktail and sitting in a quiet nook. It's definitely not a large space or a loud space, but something more to be savored and enjoyed. The bartender was extremely kind and engaging. Even if you aren't staying at the hotel, I would highly recommend coming to check this place out.

    Bar RBC - Grilled octopus

    Bar RBC

    (34 reviews)

    Bar RBC was an absolute win in our book, this place held elegance within their service that I…read morehaven't had in a very long time. When we sat we were greeted with salty, crunchy corn nuts that complemented our cocktails amazingly. We ordered promptly, with food coming out one by one, honorable mentions of the tapas was a miniature jamón baguette, that has so much fresh meat. The dates were sweet and juicy. But the main stars of the event was the flank steak, which was cooked so perfectly med rare, topped with the chimichurri. This made my jaw drop, I typically never order steak out since it tastes to much better at home. But I would pay this price time and time again. Crispy, salty and juicy with a bit of burnt ends. The bravas were also a great addition next to the steak. We ended with a sweet treat, the churros were flaming hot, so soft and plush. They tasted like lemon which was such a great surprise. The dark chocolate dipping sauce complimented it so well. We will be coming back time and time again when visited Bend.

    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 July 2026

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