San Simon is a fun little hidden gem! Tucked away down an alley, it almost feels like you're discovering 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! read more

San Simon - Cocktail Bars Near Me - Bend, Oregon

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Follow the alley. Trust me. 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. read more

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The drinks are consistently great, always made with care. The atmosphere is a fun alternative vibe. 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! read more

Absolutely love this cute cocktail bar! Nestled in an alley in downtown Bend. It's one of those places you walk by and are drawn in because it looks so cool. The outside seating has tables and cute pods with string lights for atmosphere. The interior is dark and romantic with mood lighting. We sat at the bar and I orders a Gin Gimlet which was excellent and my husband ordered an Executive Lounge- old crow bourbon, ardbeg scotch, ginger, lime, mint, rosemary. I am not a scotch fan but this drink was super tasty and more whisky forward than scotch. The complexity of this drink was incredible and well balanced. I love when I am surprised by a cocktail that is comforting, spirit-forward, both strong and smooth. Our bartender was super cool and friendly I am sorry I don't remember his name. Bend has a lot to offer but don't miss this gem. read more

San Simon - Gin Gimlet - Cocktail Bars Near Me - Bend, Oregon

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This place is a hidden gem in the alley way with eclectic vibes. They had very unique cocktails that were well thought out. The staff were very friendly and attentive. I can't wait to go back to and sit outside on a nice summer night. read more

This is a great bar with ultimate ambience. Full altar to San Simon the patron saint of debauchery inside the main seating area. Outside seating in the alleyway with little "huts" so u don't just feel like you are at a table in the middle of the alley. Service was great with lots of recommendations because all the craft cocktails look amazing so it's hard to choose. We ended up getting the gin & juice number deuce, hibiscus spritz (mocktail), and some positive feedback- all very tasty. This is a great place to grab a cocktail and sit back and relax read more

Found this lovely bar in downtown Bend, OR a 5 min walk from our hotel and down a little alley. The vibe is super cool with an altar for San Simon, the patron saint of debauchery in the middle of the seating area. The server advised that people leave trinkets or something for San Simon so he won't pester them or give them any trouble later in the evening. Of course we obliged with a little note on some MX pesos from our travels. The drinks are flavorful and strong. So many great options - we ordered the Gin and Juice Number Deuce (nice passion fruit flavor), Executive Lounge (strong and smokey) and Shrub a Dub Dub (the watermelon shrub and pickle was so good). We also got a build your own charcuterie board with marinated olives, a fancy canned tuna and smoked Rogue blue and a soft Brie. A must visit if in Bend! read more

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I love good lighting, I love a mean whiskey sour, and I love a cool, unique place I can just unwind and have a good time, with or without friends. San Simon is that place. Salud! read more

San Simon - Cocktail Bars Near Me - Bend, Oregon

Cute alley , got a bit loud when a group of 10 or so folks gathered right in front of the tiki booth ( loved the velvet curtains) we'd chosen to sit in... drinks were ok / excellent quality gin - I think you pay for the vibe- inside was really really dark but the chaise lounge seating looked comfy ... read more

San Simon - Forgot the name of the Cocktails but both gin drinks - very good gin.. - Cocktail Bars Near Me - Bend, Oregon

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Best Sazerac ever!! Every time I come in and ask for the Sazerac, it is perfect! Lovely staff, excellent service. Cheeseboard is so satisfying. Great atmosphere. You owe it to yourself to try this place if you haven't. If you have you know you wanna go back. read more

It was not about the food but an after dinner cocktail and a charcuterie board hit the spot while catching up with friends. Service was amazing and very tentative. Thank you for entertaining our jokes and keeping our drinks full. Super chill place, quiet and relaxed and just an awesome vibe to this place. read more

San Simon - Cocktail Bars Near Me - Bend, Oregon

All I have to say is... AMBIANCE! This place is so cute and perfect for date night, or just a drink with friend.

Service was very attentive with a variety of cocktails to select from. The staff was kind the only thing is they wish they had like an individual charcuterie board for one person. I was the only one in the group who wanted a little snack in my group. Unfortunately had I gotten a charcuterie. You have to individually order each item so it would've been a large expensive poured for one person.. a nice little 15- $20 individual mini board would have been really appealing! Overall it was great. The ambience, the vibe the lecture of music was phenomenal also read more

My new favorite bar in Bend, nay, in all of Oregon! Great cocktails, great atmosphere. This place is super cool without trying to be cool. It has an older, authentic feel to it... my girlfriend and I agreed it wouldn't be out of place as a funky little European neighborhood bar. Can't go wrong with any of the cocktails but don't sleep on the goat beer on tap. Delish! read more

What a fun alley bar, offering amazing drinks and a surprisingly delicious selection of bar snacks. I'm pretty sure I had the best tuna in olive oil I've ever tasted here. Despite the packed restaurant/bar, our server was incredibly nice and accommodating. read more

Classy place to have a cocktail or whatever you're drinking. There is plenty of outdoor seating. When we were there, it was cold, and the fireplace tables were in full use. We sat inside, at the bar. This place has tapped into the desires of many patrons at an upscale bar, and that is a great charcuterie plate. You can build your own from a selection of high-quality ingredients. For the olives, they make their own brine with harrissa and citrus. The portions are pretty generous, so it is easy to share. read more

San Simon - Cocktail Bars Near Me - Bend, Oregon

A true craft cocktail bar that caters to the most adventurous to the standards. We had a couple of their signature cocktails along with a Manhattan made with High West Whiskey. Seating is plentiful for singles and small groups with bar seating and small group vignettes. Service was friendly and knowledgeable. Great selection of local and National distilled spirits. read more

San Simon - A great place that is truly focused on craft cocktails - Cocktail Bars Near Me - Bend, Oregon

Wanted to do a big shoutout to the service here!! Everyone who worked with us on Saturday night, different bartenders/waiters who brought our drinks and helped us were all SO NICE AND SO COOL. You normally don't see this kind of service these days going out. Drinks were bomb. A fantastic cocktail bar! read more

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Amazing vibes, nice and dark ambience. Some of my favorite drinks are here with fun rotating seasonal drinks. The food is super expensive for what you get so i just usually come for the drinks. Great service, always greeted kindly. read more

San Simon - drinks - Cocktail Bars Near Me - Bend, Oregon

We had a lovely time getting pre dinner cocktails! Service was great and we sat outside with a fire pit. I ordered two gin drinks which were great. My friends also loved their drinks especially the mezcal paper plane. We would love to come back next time we are in bend! read more

San Simon - Cocktail Bars Near Me - Bend, Oregon

My wife and I decided to wander the downtown area of Bend a little bit and found this little gem nestled back in an alley. Outdoor seating or indoor dark room seating almost like an old speakeasy. It was very cool. The low lighting and bartenders gave off very good vibes. They did offer a small snack menu with some pickled vegetables and I believe some charcuterie assortments, but my wife and I were just there to grab a quick drink before heading off to dinner. I ordered the "Positive Feedback" which was a delicious tequila drink with a peppercorn salted rim. It was different and kind of cool. My wife ordered the "Last Blockbuster" and that one definitely won for best drink I think. It was also a tequila drink (jalapeño infused tequila) and fresh lime. It was amazing. The bartender here gave us 2 great choices for dinner, one was the Wild Rose Thai food (which we chose and LOVED), and the other was Zydeco (which he evidently designed their website which is kind of cool) which we definitely try the next time we are in town. Along with stopping back by and grabbing another couple drinks from here again. Cheers! 10/10 will definitely be back. read more

San Simon - Some Positive Feedback - Cocktail Bars Near Me - Bend, Oregon

Best cocktail bar and happy hour in Bend, period. Possibly in all of the PNW. Been coming here entirely too often for the past 5 years and don't plan to stop anytime soon. read more

The new bartender needs more training, the cocktails were mediocre. The location is great tucked away in a quiet alley just off the main streets of downtown. read more

Excellent cocktails! Fernaiquiri was great and the Sazerac on happy hour was spectacular! Super cute inside, fun outside seating, and nice people. read more

San Simon - Sazerac and Fernaiquiri - Cocktail Bars Near Me - Bend, Oregon

Sophisticated Debauchery indeed ! Down the dimly lit alley lies this fantastic bar that we returned to ,two days in a row . Inside it's cozy and warm, like dusk on a Fall evening . The bar has a moody intimate vibe and the décor is whimsical with a permanent shrine In there .Outside there are tables with gas fires and little cubbies with heaters . we sat at the bar and started with some delicious cocktails . The bartenders were fun and chatted a bit about the choice of alcohol and ingredients . The next round of cocktails ,was something that my hubby requested based on his preferences and they delivered 10/10. We had already had dinner before we came so just stuck to drinks but the charcuterie did look appealing . Service and overall attentiveness of both the bartenders was amazing ! Highly recommend! read more

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I brought my girlfriend to San Simon for her first visit and she loved it! Brian treated us like friends and wasn't put off by her questions on the cocktails. Good job Brian! She loved hers and I order the same after dinner drink everytime because its that good! She had the one with rum, cappelletti, pimento dram, pineapple, lime... I ordered the signature San Simon espresso martini which reminds me of those chocolates at Christmas shaped like an orange that you slam on the table and little chocolate orange slices break apart... Delicious.. We'll be back! read more

San Simon - Signature Espresso Martini (over ice) - Cocktail Bars Near Me - Bend, Oregon

Man , I gotta say , a lot of bars downtown have these kids that work there that suck at their job because they think they're super cool or don't wanna be there ... NOT THIS PLACE ... every single person working Saturday night was so nice and friendly and welcoming , super sweet , positive , funny and helpful , all those kids were amazing , my wife and I had a blast , loved the vibes and the music .. it was very dope .. read more

Upgrading to five stars. San Simon is simply a jewel in this town. Superb drinks, sublime ambiance, Bend-friendly service. I'm not in love with the sometimes too loud music but the past couple of visits its been toned down. read more

San Simon - Cocktail Bars Near Me - Bend, Oregon

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Went for a pre-dinner cocktail. Asked for a rum and coke with Cruzan rum and the server laughed at me because I didnt want one of their craft cocktails. She asked if I was from the Midwest and then asked if I was sure I didn't want Captain Morgan instead. No need to be snotty, just say yes or no. The actual rum and coke was good so I'll give it two stars. read more

Total bust! Upon arrival we were quickly offered a seat at a corner table inside or a choice of 4 open stools at the bar. We chose 2 of the open stools. My husband and I each ordered a drink from the bartender literally right in front of us. She feverishly made drinks over and over, but not ours. When the couple who sat next to us well after we arrived received their drinks before us, and the empty table we were offered had a couple seated with drinks half gone and 30 minutes had painfully clicked by for us waiting and waiting, we left. Waiting 30+ minutes with a bartender right in front of us is unacceptable. read more

San Simon - Alley entrance and outdoor seating. - Cocktail Bars Near Me - Bend, Oregon

Good music good vibes and happy hour drinks were delicious best of all the staff was so kind and attentive!

This is a sexy little cocktail bar semihidden in an alley. It's a decent place for a date, as they have a nice ambience conducive to romance and flirting. They also have a cool shrine with a photo of MF Doom! I was recently there for a blind Bumble date which didn't work out but the service was great. I will definitely come here again for drinks What's not to like? read more

San Simon - MF Doom at their altar! - Cocktail Bars Near Me - Bend, Oregon

Such an amazing intimate spot to get some unique cocktails. The bartenders are always super nice and will chat with you at the bar. All of their drinks are well balanced and very tasty. A special Bend spot. read more

San Simon - CBD drink (left) and a gin drink (right) - Cocktail Bars Near Me - Bend, Oregon

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Great atmosphere!! Friendly staff. Wonderfully creative drinks. Light menu. Great place to meet friends.

First place of the night and it was a great start. Got a little cheese board snack to go with some fantastic drinks. Hunkered inside away from the heat and we're treated to a talented bartender working his craft. The old fashioned was great (both the drink and salami). read more

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Cocktails are delicious. Service is incredibly friendly and fast. We went twice and the server from the first visit recognized us and came over with a small sample of a delicious watermelon drop for each of us. Cool atmosphere. Reasonably priced for the quality. Favorite spot in Bend. read more

San Simon - Cocktail Bars Near Me - Bend, Oregon

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It was ok. We were hoping for something more. The ambiance was just missing something. The drinks were good but charcuterie board was just ok not the best we've had. Service was good. It would be awesome with some pool tables or something else to make it less empty and more entertaining. read more

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Came here based on being a highly recommend hot spot for Bend. Staff is friendly. Had one of the more popular drinks, The Last Blockbuster, for jalapeño infused tequila...definitely opened up my brain cells with bold flavors. Most of the cocktail menu is $13 per drink so reasonable and average for a cocktail bar. Has some outdoor heated seating and dark interior ambiance making it feel fairly private for the groups hanging around. Quite a few mocktail/low-alc options so recommend for groups with mixed drinking preferences. Follow up....go to the bathroom, look up. read more

Everything is perfection every time. From the drinks to the atmosphere to the bartenders. 100/10 every time. Best bar in Bend hands down.

Ok bar, feels very Portland. Would probably not come again Recommend investing in a meat slicer read more

San Simon - Old fashioned - Cocktail Bars Near Me - Bend, Oregon