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

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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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

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

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

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

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

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

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

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

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

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

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

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

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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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

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

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

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

Stopped in for a drink before dinner. The house made tonic was exceptional! The vibe was mood lit, energetic and simultaneously chill. We had a wonderful charcuterie. Everything was thoughtfully sourced. Tasted great. We'll be back with friends! read more

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

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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This place is a gem hidden down an alley the vibes are on point. The inside is dark and moody with a welcoming staff and really fun cocktails. You can also make your own charcuterie by choosing items sushi menu style, so fun. Highly recommend & am looking forward to going back. read more

San Simon - Cocktail Bars Near Me - Bend, Oregon

Cute vibe, great staff, and wonderful drinks. I also really love their little bites to eat.

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

GREAT cocktails!!! The vibe was swanky and dark. Staff was great! San Simon is a bar!!!

Everything was great. We opened the door not knowing what to expect and got pulled in by good people and great vibes. We will go back for sure. read more