First of all- I just moved here and I keep hearing this is "the bad part of town" and no, it's not…read more We passed one unhoused person who was just minding his own business. Don't be afraid to come here! Lots of food truck options which is cool. My friend and I each got zero proof cocktails. She got the sweet hemptation and liked it so much she got a second one. I got the funky cold Modena which was tart and tasty. And we got to see Miz Cracker from RuPaul's Drag Race!! So fun! The drag show was high energy and a great time.

I'll preface by stating that this establishment is a bar with a food truck lot. It is not the…read moreDogwood downtown cocktail bar that is the subject of the prior hundreds of reviews. The owners closed up shop downtown and created this new place on 2nd Street in Bend's Central District. It's now called Dogwood at the Pine Shed. Why Yelp won't create a new, distinct page for the Pine Shed is beyond me. That said, the Pine Shed is a fine place for drinks and food truck fare. The open, spacious 'shed' has plenty of varied seating surrounding a nice bar with quite a few tables outside on the patio. Mobility-challenged folks have choices too. For those worried about 2nd Street's reputation for sketchiness, don't be. Revitalization efforts by the city have transformed the area. At times of good weather, with the big doors open, the Pine Shed is quite a nice spot to relax. Cocktails were the raison d'etre for the former incarnation of Dogwood and that emphasis transfers here to the Pine Shed. I particularly like their versions of a margarita but the other cocktails are uniformly good too. The beer tap offerings are not so spectacular, however, with only four (and a cider). On one visit shortly after they opened for business, two beer taps were tapped out, which can be chalked up to growing pains. In any case, the Pine Shed can't be seriously regarded as a tap house in the style of the many others in Bend (On Tap, River's Place, Crosscut, The Lot, The Podski, Midtown Yacht Club, etc.). Come for the cocktails. They do offer low ABV and zero ABV drinks. At present, the food truck choices are abundant and pretty decent. Being trucks/carts, and thus mobile and prone to relocating themselves, I'll not list them here. Best to check the Pine Shed's webpage for current offerings and then go to the relevant Yelp page for reviews. Parking is street only, no parking lot. The city has completed construction on 2nd Street so there are more spots available than before.

First day of my work trip arriving in town. The hotel highly recommended visiting here. Sunday 7pm…read moreis quiet but I'm not upset. Bartender was friendly and knew his mixology well! I didn't order food but I'm sure it's delish! My drink was yummy and the decor is rustic and modern. I liked that the place felt clean too.

I've loved Velvet for years, at least the idea and aesthetic of it. Really well curated interior…read morewith a great ambiance. The owner is the only person I've felt good vibes from. The rest of the team, especially recently, have unfortunately always had frankly unwelcoming, bored, avoidant, unenthusiastic, dead expression attitudes no matter the time or stress level. I've even been in when zero customers were in the entire building and based on the sole interactions with the bar, or lack thereof, the magic gets leached away from the place. Without the bartenders, it's just an empty building after all. A welcoming attitude or some conversation is the warm hearth that brings cold travelers back over and over again; people remember how they feel. Then again, even when the place is packed with people, I don't feel any warmth or connection from anyone here. Maybe it's a sign of the times, maybe it's Bend in general. I'll keep trying and coming back nonetheless.

There appears to be a serious violence problem with some of the staff at the Astro Lounge. One or…read moretwo of the bouncers nearly killed two people last week by kicking already unconscious individuals lying on the ground hard in the head a few times. Instead of using their certified de-escalation skills to safely break up a fight, my friends and I had to rip these people away and call 911. It's really concerning.

food is bad. service is terrible. ambience leaves a lot to be desired. The place is pretty dirty…read moretoo.

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!

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.

Stopped by Hawkeye & Huckleberry for drinks before dinner and absolutely loved the vibe! The whole…read moreplace has a super cute modern country western theme with fun decor and cozy tent-style dining areas that make the atmosphere feel unique and inviting. We grabbed seats at the bar and tried the Tumalo Honey which was a fabulous blackberry-forward cocktail that was refreshing and perfectly balanced. We also had the Doc Holliday, which was like a sweeter twist on an Old Fashioned and incredibly smooth. The drinks were great, the ambiance was on point, and the vibes were definitely there. Such a fun spot to relax and start the evening. We'll definitely be back for dinner and live music when we're in town next!

We stopped in H&H on a Saturday evening, and the place was loud and lively. We were a party of 12,…read morein a private room, and we were seated right away, despite being a few minutes early. This establishment tries to be cowboy, but they just end up hipster cowboy. It's all fun, regardless. Our drink and appetizer orders were taken promptly, and brought out pretty quickly. The pork belly app had good flavor, but not sure it's worth the price. The "Barrel Racer" drink, however; was good enough that I ordered a second one (basically a cucumber margarita). Sometime in there, four of us did a shot-ski, which is four boot shaped shot glasses mounted to an old wooden school. They didn't have the best tasting tequila available, but it was still fun. For a main dish, I went with the Oregon Coast Salmon entree. The fish was cooked to perfection, and tasted very fresh. The accompanying sauce wasn't quite as impressive, but still good. The best part of the meal was the beef Fat Fries -- probably about the best fries I've ever had. They were golden brown, with a crisp crust, and a soft velvety interior. I'd go back again just for those. None of our group wanted dessert, other than four who wanted to do an espresso martini shot-ski. While the food was good, and we all had fun, there are options in Bend that offer more excitement for the palate, at a similar price point.

Classy place but also laid back and relaxed. Wasn't overly loud so we could carry on a conversation…read morewithout a problem (which isn't the case at another bar around the corner). Good drinks and appetizers. Nice staff.

Great little bourbon bar in Bend. Outdoor seating makes it pet friendly. Good French 75's as well).read more

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.

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.

Good music good vibe, kind of a hidden gem. From the single door entrance on Oregon st you wouldn't…read morethink it would have such a long bar, ample sitting areas and room for live music and dancing

Dive bar now masquerading as a kid-friendly arcade. And not a dive bar in the good sense. Dive bar…read moreas in turn around and go to D&D or Corey's.

I came here two different times while visiting Bend…read more My first time was to grab a drink before meeting someone for dinner at another restaurant. The Smokey pineapple mescal drink was really good. I would definitely recommend. I came here another night on HH. I got the ceviche and a pineapple margarita. Both also equally delicious. The service here was very slow and I had been sitting at the bar which was strange.

Best margarita of my life!…read more Love the vibe of this restaurant. Food and drinks were 10/10. They have indoor seating and a back patio. This place was quite popular when we went on a Saturday afternoon.