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The Gallery Restaurant and Bar

3.3 (192 reviews)
ModerateLounges, American
Open • 9:00 am - 10:00 pm

THE GALLERY RESTAURANT AND BAR · YELP ASSISTANT

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THE GALLERY RESTAURANT AND BAR ATMOSPHERE

What's the vibe?
Casual
Moderate noise
Outdoor seating
Good for kids

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Outside
Cawnii P.

Drove up to visit Sisters, walked around the town and stopped in THE GALLERY for lunch. It was a warm day so we indulged in a VERY COLD PILSNER. Also had a hamburger and a patty melt with fries and onion rings. The beer average 5* lunch 3* = 4

Prashanth N.

Great location, right off the main street in Sisters. The restaurant was packed busy for Saturday. Too bad, I missed the breakfast menu, I really wanted to try one of the Benedict dishes. so I got the vegetarian quesadilla and it was pretty good and filling. The waitress was friendly and fast. The main area was packed full, so we were seated at the open tables, near the pool tables, with nice big windows. They something for everyone of us - Vegan, Vegetarian and non-vegetarian dishes.

The Gallery Restaurant and Bar: Greek Salad minus feta, avocado added
Chiemi N.

We're staying at the nearby Black Butte Ranch. We spent the morning traipsing around Dee Wright Observatory, and we definitely built up an appetite! We walked around the quaint town of Sisters in search of a place to have lunch. The Gallery Restaurant looked promising. We entered behind another group. We waited for a while. The group in front of us decided they didn't want to wait any longer, and left. We were actually thinking the same thing when someone came over and told us we could seat ourselves at an open table. The waitress was friendly, and took drink orders right away. After that she took our food order. I got the Greek Salad without the feta, and they subbed avocado for me. I got the balsamic vinaigrette on the side. It was pretty good! My friends all enjoyed what they got!

Prime Rib dinner

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6 months ago

Excellent food and service. Enjoy walking the town of Sisters, especially when it is snowing.

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9 months ago

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5 months ago

We are in agreement with the two star post. Food is substandard, servers are average or below at best and the ambiance lacks.

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4 months ago

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11 months ago

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1 year ago

Zoey was the best! As always, attentive and the drinks were perfect! Will come back for sure!

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2 years ago

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4 years ago

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2 years ago

Best hambuRoger and fries I've had in a long time. Great service and super friendly. I'lk be back!

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Wayfarer Club - Hmmm...a bit disappointing. Only writing this in hopes that they'll get their offerings to match their cool Vibe!

Wayfarer Club

4.2(22 reviews)
18.7 mi
Happy hour specials
Full bar

Participated in a wedding rehearsal buffet dinner with signature cocktails, far exceeded my…read moreexpectations. The array of food was excellent & enjoyed one of the signature drinks. Since they have opened been to the dining venues 4 times, just keeps getting better. I must try the Wayfarer. The serve staff was attentive. Ambiance charming on the upper deck & accommodated 50 guest comfortably. Highly recommend check out the facilities at the hotel.

We were a party of 5 that was surprised by the rude service of the bartender. The bartender looked…read morebusy so we went to the bar for menus. There were 6 other people in the bar. We were told to have a seat and she'd bring us the menu. After we decided we went back to the bar and was told to sit back down that she'd get to us. I told her no rush, I can wait. She then replied, "I have these drinks to make and when I'm done, pointed to the dishes she had to get to first." I went back to the table and we left. We had planned to order drinks and food. Was the place understaffed? Did they not have enough dishes and glassware to support the guests? Was she insensitive to minorities? Regardless, I venture to say that I have been in "customer care" for more years than the age of the bartender. There have only been a few other instances that I've been treated this way. Extremely disappointing! Will never go there again and will never recommend this bar.

Photos
Wayfarer Club
Wayfarer Club - Granny Brie - IG @bougiefoodieboi

Granny Brie - IG @bougiefoodieboi

Wayfarer Club - Great views on the 4th floor!

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Great views on the 4th floor!

San Simon - Gin Gimlet

San Simon

4.7(109 reviews)
20.0 mi
•$$

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

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 - Aperol popsicle in cava.

Aperol popsicle in cava.

San Simon - Bourbon

Bourbon

San Simon

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The Gallery Restaurant and Bar - lounges - Updated November 2026

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