Moose Sisters

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.

Funky Cold Modena non-alcoholic cocktail

Tiny beer with Tequila shot

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The Bar

Flamingo Room

4.7(43 reviews)

3.8 mi

Great crowd of people all ages. Very welcoming and even when they are busy. I want to go more to…read morethis one.

Cool spot. Didn't have to wait too long. Cool mix of interesting flavors. Service was good. All the…read morefood options looked pretty weird so didn't end up ordering any.

Bar

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San Simon

4.7(106 reviews)

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.

Gin Gimlet

Bourbon

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San Simon in Tin Pan Alley

Dear Irene

4.7(86 reviews)

2.9 mi

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.

Fun bathroom art

Scallops

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Cocktail

Amaterra Kitchen + Social Club

4.6(31 reviews)

Shawn G here. I don't post a lot of reviews, but I'm starting to share only the greatest hits--the…read moreplaces that really stand out--and Amaterra in downtown Bend makes that list easily. This is a membership experience as much as it is a restaurant. The architecture and design are divine: floor-to-ceiling wine cases, a beautiful fireplace lounge, and that city-meets-cellar feel with the wine barrel walls. It's the kind of place you actually want to sit in and take in, not rush through. If you're looking for spots worth paying attention to, this is a good one to start with. I'll be back.

I'm so glad we got to go here! There's an Amaterra in PDX which I've been meaning to go to but…read morehaven't yet. Now I have to go! The ambiance inside is beautiful. Simple and modern. I had the Syrah which I really wanted to take a bottle home but I have too many bottles at home as is. A good problem to have I guess. Frank, our waiter was fantastic. He was a bit busy, but always courteous and checked in a few times. My husband and I were happy with our food, but my brother who had the pork said it wasn't flavored enough.

Bottle of Amaterra wine and a coctail on the bar at Amaterra Kitchen + Social Club.

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WildWood

4.6(43 reviews)

3.5 mi

Food is fantastic, the bartender is always lovely, and such a mellow and cool vibe to spend a lunch…read moreor evening in.

The restaurant looks nice and has a good vibe but that's all it has going for it. We can hear a…read morewhile back and the food was great but they changed the menu and it's horrible. I ordered the chicken and fries. The chicken is super dry with no flavor and tastes like it's fried in old dirty oil. Also the beer options are seriously lacking. Whatever they were doing years back they need to return to. The baked mac and pulled pork sando they used to serve was out of this world.

Downstairs seating

Upstairs seating area

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Beer and fire, what's not to love

Velvet

4.4(169 reviews)

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.

Great GiClee art prints on the wall in the upstairs lounge.

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View from the top in the upstairs lounge.

Broom Closet

4.6(50 reviews)

3.2 mi

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.

Passport

Ceiling made out of broom party with quotes

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Lady Bird Cultural Society

4.2(158 reviews)

3.8 mi

Very wonderful happy hour; and...the best espresso martinis in town!!…read more Went back for dinner; delightful experience!

Unimpressed. Loved the interior, the drinks were fine, the brussel sprouts were good...but service…read moreis what makes a spot and a cute interior can't make up for lack of good service. We were seated at the low seats at the bar but weren't given menus, so I had to walk up to the hostess stand for them after waiting for a decent amount of time. The red-headed bartender/server tried to walk away after taking our drink order and had to stop him from walking away to order food. There were no check-ins at the table, a hostess walked around once filling everyone's water but that was it (so we had empty water for about half the time we were there), I had to flag down the bartender by staring at him from across the bar to get his attention for a check, once I got the check he again tried to immediately walk off even though I had the card & wallet on the table and nearly immediately put it in the book, and in general he was not amiable. I actually asked my friend after the first interaction of 'do you think he's having a bad day or hates it here?'. Lastly, the oysters are listed as 'oysters' with no description but they are not normal oysters - they have green vinaigrette, some roe type orange topping, and personally weren't enjoyable. 2.5 for service and not listing ingredients. 3 because the brussel sprouts and drinks.

The pictures do not do this place justice.

Bone marrow & escargot

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Old Fashioned

Bar RBC

4.6(32 reviews)

Absolutely the best restaurant we went to while we were in Bend for a long weekend. The service was…read moreamazing, recommendations were on par with expectations and food is second to none (at least compared to other restaurants we tried). Highly recommend any of the potato dishes and the pork. Place is sharable plates and made it great to have a family style with the group. got to try everything we ordered. When I'm back in Bend, i will definitely be coming back here even if its just me.

Shout out to Corrine and Kim for taking care of us. Thank you Corrine for all the great…read morerecommendations! Swung by here after spending a day at Crater Lake National Park. Parking is a bit challenging. Inside the space is a little dark, and it had a nice ambiance. The noise level is a medium. You need to speak up a little but you don't need to shout to be heard. We came without reservations, luckily for us two seats at the bar opened up so we were seated right away. Since it was our first time here we asked Corrine out for some recommendations. She talked through some of the popular dishes and also some of her personal favorites. We ordered... Food - El Bulli Olive: Fun bite if you're an olive fan. Creative gastronomy creation. - Toro Radicchio: Really tasty salad, with great flavors. - Fried Anchovies and Artichoke: Delicious! If you're an anchovies fan, get this dish. One of my favorite bites of the night. - Iberico Secretto: Meat imported from Spain. Great flavors. Drinks - Pamplemousse Spritz: Refreshing n/a cocktail. Definitely would get again. - Strawberry-White Peppercorn Shrub: One of my favorite n/a cocktails I've had to date, would recommend. Dessert - Tarta De Santiago: Solid dessert.