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    O’Kanes

    4.0 (29 reviews)
    Closed 3:00 pm - 11:00 PM

    O’Kanes Cigar Bars Photos

    O’KANES ATMOSPHERE

    What's the vibe?
    Quiet
    Casual
    Outdoor seating
    Good for groups

    Recommended Reviews - O’Kanes

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    Reviews With Photos

    Rye sazerac cocktail--delicious and new to me
    Joan F.

    Wow, this place always delivers! My first sazerac cocktail, and I'll never look back. The bartender artfully, lovingly made this amazing drink from New Orleans. Smoky and with hints of licorice, this is my new, favorite cocktail. We enjoyed our drinks in the shady, garden patio. Perfect on a mid September afternoon. If you hate cigar smoke--and I can see why you would--this outdoor patio may not be for you. There was enough breeze to lighten the smell. Time after time, this is one of our favorite aspects of the Old Saint Francis School at McMenamins.

    Seating area
    Christina S.

    Let's hope this part of the popular McMenamin's stays the "great hidden gem" it is! I was told to come here by my brother-in-law who frequented O'Kanes before Yelp was even a thing. At night it's dark and intimate, cigar smoke fills the air and you can warm up by the wood burning stove. The Old Fashioned I ordered to sip on was just right. It's small so there's limited seating inside where you're surrounded by beautiful stained glass, Grateful Dead posters and music and the story of O'Kane on the wall behind the bar. Outside is a spacious patio with fire pits in the winter.

    @mikegthatsnice (all social media) AmericanCigarFederation.com
    Mike G.

    Great little bar with wood stove and fire pits, have schists for sale and can smoke inside and out. Friendly staff. Great spot to just chill and be low key.

    Cheers to awesome times with friends
    Karri M.

    Great hidden gem! Definitely a local's favorite. Fire pits, whiskey, cigars and beer, you can't beat that!

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    4 months ago

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    1 year ago

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    2 years ago

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    3 years ago

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    4 years ago

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    6 years ago

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    4 years ago

    No absolutely love the retro feeling of sitting in a light haze of cigar smoke in a dimly lit old building. So cool

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    10 years ago

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    11 years ago

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    3 years ago

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    8 years ago

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    10 years ago

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    12 years ago

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    11 years ago

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    8 years ago

    Very pleasant to sit outside on the patio in the summer. Lance was our server and did a great job! The gyro was yummy.

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    9 years ago

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    10 years ago

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    9 years ago

    This is a great spot to hang out and relax. It's a great opportunity to socialize with someone new around the fire pits and enjoy a drink.

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    9 years ago

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    11 years ago

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    9 years ago

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    13 years ago

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    12 years ago

    Cool woodsy taverny little cigar and whiskey bar. Fire pits and decor are awesome. Drinks were good. Fun place to take friends.

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    11 years ago

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    10 years ago

    Pricey and food is average. However you go and pay for the extensive knowledge and drink selection and the giant fires outside.

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    10 years ago

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    13 years ago

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    Ask the Community - O’Kanes

    Review Highlights - O’Kanes

    Great little bar with wood stove and fire pits, have schists for sale and can smoke inside and out.

    Mentioned in 10 reviews

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    People searched for Cigar Bars 207 times last month within 10 miles of this business.

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    Dogwood at The Pine Shed - Indoor seating and south side entrance

    Dogwood at The Pine Shed

    4.3(263 reviews)
    0.5 mi
    $$

    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.

    Photos
    Dogwood at The Pine Shed - Funky Cold Modena non-alcoholic cocktail

    Funky Cold Modena non-alcoholic cocktail

    Dogwood at The Pine Shed - Tiny beer with Tequila shot

    Tiny beer with Tequila shot

    Dogwood at The Pine Shed - The Bar

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    The Bar

    San Simon - Aperol popsicle in cava.

    San Simon

    4.7(106 reviews)
    0.1 mi
    $$

    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.

    Photos
    San Simon - Gin Gimlet

    Gin Gimlet

    San Simon - Bourbon

    Bourbon

    San Simon - San Simon in Tin Pan Alley

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    San Simon in Tin Pan Alley

    Dear Irene - Scallops

    Dear Irene

    4.7(86 reviews)
    0.2 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.

    Photos
    Dear Irene - Fun bathroom art

    Fun bathroom art

    Dear Irene - Scallops

    Scallops

    Dear Irene - Cocktail

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    Cocktail

    Lady Bird Cultural Society - Pear Tarte Tartin

    Lady Bird Cultural Society

    4.2(158 reviews)
    0.6 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.

    Photos
    Lady Bird Cultural Society - The pictures do not do this place justice.

    The pictures do not do this place justice.

    Lady Bird Cultural Society - Bone marrow & escargot

    Bone marrow & escargot

    Lady Bird Cultural Society - Old Fashioned

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    Old Fashioned

    O’Kanes - cigarbars - Updated May 2026

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