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    The Restaurant at Awbrey Glen

    4.1 (7 reviews)
    ModerateDiners, American, Bars
    Open 11:30 am - 8:00 pm

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    2 months ago

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    12 years ago

    Great service and a Pino . Great find. Traditional fine food with a great wine selection. Not packed, great for an intimate dinner.

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    13 years ago

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    9 years ago

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    10 years ago

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    12 years ago

    Great service and fantastic food! Good happy hour too. I will always recommend to friends and family!

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    9 years ago

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    Cassity's Bar and Grill

    Cassity's Bar and Grill

    3.6
    (12 reviews)
    2.1 mi

    When you don't know what you want to drink ask Simone at Cassitys to make you something special…read more She has never steered me wrong.

    Cassity's seems to be Cabin 22 with a few minor changes. I'll review based on the changes although…read moreI was never a regular at Cabin 22. - Menu is upgraded, although it still says 'soft opening menu.' Includes things like pho and a Nashville sandwich (what I ordered - it's decent, spicy, but won't displace any fond memories of Hattie B's in the South). What's missing is anything at all for vegetarians, except salad and a few fried snacks. A Beyond burger would be a great addition. As it is, my wife will definitely not come here. - Seating is much the same except with mostly six-seat high tops. I believe Cabin 22 had low tops. Mobility-challenged folks might have trouble finding a spot. The patio outside is nicer, although the proximity to 14th street might render it a bit noisy. The bar is much the same. - Good tap list with lots of choices, including local beer. - Prices are in line with what you'll find in Bend these days for food and drinks. - Service might be a bit wonky what with the 'order at the bar' signs on the tables. During our visit, the bartender immediately came over to take our order and frequently returned. It wasn't busy so that might not be the norm. Bend friendly service. - I mentioned mobility-challenged folks: what hasn't changed are the restrooms. If you're wheelchair bound, you're screwed. No way to even get into the restrooms with those really narrow doors. I would have hoped the new owners would fix that ADA failure. They're also too small for the size of the restaurant. Overall, four stars. Seems like a good hangout joint for most folks. I'd be interested if the menu changes from the soft opening offerings.

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    Pool table
    Pool table
    Cassity's Bar and Grill
    Simones pink drink

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    Simones pink drink
    Hawkeye & Huckleberry Lounge

    Hawkeye & Huckleberry Lounge

    3.8
    (171 reviews)
    2.3 mi
    $$$

    Well, we did not know what to expect, and it was not what we expected. If you are looking for…read moreintimate dining, this is not the place. There's loud music, it's very dark, set up like a cafeteria with hard chairs and tables with no intimate space unless you reserve a tent. Our servers were awesome, the atmosphere was fun, the steaks were a little overpriced. They were probably 15 to 20% higher than most steakhouses that I eat at. If it was a higher end intimate location, I can see the extra price, but it misses the mark as far as fine dining. No complaints. I get why people like it and I'll know what to expect if I go back next time. Ok one complaint. The steak frite was salty as hell. Steak not fries... I'm sure it was just the seasoning but way way way too salty. Parking sucks!

    I just found a Bend‑themed restaurant where the vibe is actually insane. Like... Eastern Oregon…read moreaesthetic, cozy‑rustic energy, and service so good. We kicked things off with the Hawkeye Burger it was juicy, stacked, flavor then added the beef fat fries. The crispy pork belly? Perfect crackle. The Caesar salad? Cold, crisp, and actually seasoned (rare). And the whole place is themed around Bend -- different rooms, different vibes, all super intentional and super cool. Happy Hour every day from 4-5. Live music Fridays at 8. Honestly... this spot is a whole experience.

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    Hawkeye & Huckleberry Lounge
    Pepperoni and sausage pizza with hot honey
    Pepperoni and sausage pizza with hot honey
    I'm Your Huckleberry and Midnight Cowboy

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    I'm Your Huckleberry and Midnight Cowboy
    San Simon

    San Simon

    4.7
    (107 reviews)
    2.4 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.

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    Gin Gimlet
    Gin Gimlet
    Bourbon
    Bourbon
    San Simon in Tin Pan Alley

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    San Simon in Tin Pan Alley

    The Restaurant at Awbrey Glen - diners - Updated June 2026

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