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    The Gallery Restaurant and Bar

    3.3 (185 reviews)
    ModerateLounges, American
    Open 9:00 am - 10:00 pm

    The Gallery Restaurant and Bar Photos

    Business Info

    THE GALLERY RESTAURANT AND BAR ATMOSPHERE

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

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    Recommended Reviews - The Gallery Restaurant and Bar

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    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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    3 months ago

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    11 months ago

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

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    1 year 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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    2 years ago

    Came here for breakfast. The chicken fried steak was amazing! Would definitely come back here again!

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    San Simon - Aperol popsicle in cava.

    San Simon

    4.7(106 reviews)
    20.0 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

    Famille - Crab cakes

    Famille

    3.5(33 reviews)
    0.2 mi

    First visit - opening week. The bar remodel is stunning. The dining room feels much lighter, and…read moreless crowded. The hostess was fantastic - some great strategizing to ensure a relaxing time at the bar, while still having a reserved table for dinner. This was a meal of starters (one of my favorite ways to check out a menu): the grilled Romaine salad was fantastic, the crab cakes were lovely (I would really love to know the recipe for the remoulade- super yumm). Both the steamer clams and the tuna stack are sizable - great for sharing. The wait staff in the dining room were personable and attentive. This is intended to be a space that can go from day to night and I could easily see savoring a coffee here in the morning or meeting friends for happy hour. Only negative was some pacing issues re timing for drinks when we were at the bar. However, given how much it takes to launch a restaurant, and that this was opening week, I think that is something that will likely be worked out. Look forward to coming back and trying out other parts of the menu.

    Two days after Christmas, we celebrated two family member birthdays at Famille. It was wonderful…read more There were 9 of us and the service was excellent. Everyone thoroughly enjoyed their food and we appreciated the wide range of menu items that met the needs of our varied diets. Even the 2 year old loved his mac and cheese. [Be aware, they don't have high chairs.] The best part of all, I have a hobby of rating expresso martini's all across the world. I've rated 33 so far. And much to my surprise, Famille made #1 on the list! They beat out London, Kenya, Yosemite, Canada, Italy, Switzerland and more. The bartender is excellent and she is a kick, so be sure to say hello or Aloha [she's from HI]. Thank you!

    Photos
    Famille - Le Bar

    Le Bar

    Famille - Their French Onion soup

    Their French Onion soup

    Famille - Bar seating

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    Bar seating

    Three Finger Jack - Turkey sandwich bursting with flavors soooooo delicious.

    Three Finger Jack

    4.0(33 reviews)
    0.3 mi

    I wanted to share my experience at Three Finger Jack in Sisters, Oregon! I had read some negative…read morereviews before going, but I'm happy to say our experience was excellent. I'd suggest checking out their website as well, it shares their personality of this restaurant. We visited on a Tuesday night shortly after they opened. The place was busy, full of happy people, and the energy was great. We sat at the bar and patiently waited for the staff--understandably busy with a full house. The service was wonderful, and the drinks were fantastic. We ordered the shrimp tacos, and they were delicious--definitely worth it! I also really appreciate that they support local vendors, like Sisters Smoke House and Sisters Bakery. We had a great experience and will definitely be back!

    If you're looking for amazing food and great service, definitely stop by Three Finger Jack. I had…read morethe shrimp po' boy, and it was absolutely delicious -- perfectly seasoned, generously filled, and full of flavor. The atmosphere is cozy and welcoming, making it the perfect spot to relax, enjoy a good meal, and watch some football. Whether you're dropping in for a quick bite or settling in for the game, this place hits the spot. Highly recommend!

    Photos
    Three Finger Jack
    Three Finger Jack - Meatloaf with mashed potatoes and green beans. Soooo good!!

    Meatloaf with mashed potatoes and green beans. Soooo good!!

    Three Finger Jack - Tequila Shrimp Tacos  Charred shrimp splashed with tequila, garlic, and lime. Crisp, vibrant, and riding the line between bold and smooth.

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    Tequila Shrimp Tacos Charred shrimp splashed with tequila, garlic, and lime. Crisp, vibrant, and riding the line between bold and smooth.

    Hawkeye & Huckleberry Lounge - Grilled seasonal veggies

    Hawkeye & Huckleberry Lounge

    3.8(164 reviews)
    20.0 mi
    $$$

    We stopped in H&H on a Saturday evening, and the place was loud and lively. We were a party of 12,…read morein a private room, and we were seated right away, despite being a few minutes early. This establishment tries to be cowboy, but they just end up hipster cowboy. It's all fun, regardless. Our drink and appetizer orders were taken promptly, and brought out pretty quickly. The pork belly app had good flavor, but not sure it's worth the price. The "Barrel Racer" drink, however; was good enough that I ordered a second one (basically a cucumber margarita). Sometime in there, four of us did a shot-ski, which is four boot shaped shot glasses mounted to an old wooden school. They didn't have the best tasting tequila available, but it was still fun. For a main dish, I went with the Oregon Coast Salmon entree. The fish was cooked to perfection, and tasted very fresh. The accompanying sauce wasn't quite as impressive, but still good. The best part of the meal was the beef Fat Fries -- probably about the best fries I've ever had. They were golden brown, with a crisp crust, and a soft velvety interior. I'd go back again just for those. None of our group wanted dessert, other than four who wanted to do an espresso martini shot-ski. While the food was good, and we all had fun, there are options in Bend that offer more excitement for the palate, at a similar price point.

    Underwhelmed 1st time trying Hawkeye. The service was not attentive our waiter seemed too busy. My…read more$75 ribeye was undercooked - this too me is inexcusable. Potatoes Came out hard and overcooked Combined with sporatic service = bad experience. A lot of hype no substance

    Photos
    Hawkeye & Huckleberry Lounge - Event space

    Event space

    Hawkeye & Huckleberry Lounge - Pepperoni and sausage pizza with hot honey

    Pepperoni and sausage pizza with hot honey

    Hawkeye & Huckleberry Lounge - I'm Your Huckleberry and Midnight Cowboy

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    I'm Your Huckleberry and Midnight Cowboy

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

    Dogwood at The Pine Shed

    4.3(263 reviews)
    20.2 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

    The Gallery Restaurant and Bar - lounges - Updated May 2026

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