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    My Way Lounge

    4.7 (16 reviews)
    Closed 3:00 pm - 2:00 am (Next day)
    Updated 3 months ago

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    Margarita Time Cheers!

    I have been to this lounge a couple times now, they mainly play hip & hop and r&b love it! Parking is very accessible plenty of space in the parking lot. The drinks are yummy and decently priced, we hadn't tried the food yet but maybe next time. Super cute, chill and intimate lounge. The bartender Sam was attentive and friendly. Highly recommend for chill night with friends.

    two glasses of blue and green drinks

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    4 months ago

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    4 years ago

    Very cool vibes and great selection of drinks! Fun hangout spot to play lottery, drink, watch sports, etc

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    Review Highlights - My Way Lounge

    Been coming to My Way for a few months and it never disappoints.

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    The Observatory

    The Observatory

    4.3
    (2.6k reviews)
    3.0 mi
    $$

    Had an awesome time at The Observatory the other weekend. Unlike a lot of places, they run their…read moreHappy Hour on the weekend, which is what drew my partner and I in. You can absolutely smell the fish and vinegar as soon as you walk through the door, which I think gives the place a very homey pub feel. I ordered a spiked peach Arnold Palmer, which I enjoyed (and it was pleasantly strong) and a glass of the house white, which was good for the price. Our server was very fast and attentive. To eat I got the tomato soup with a grilled cheese, which was absolutely fantastic. The soup was so creamy and flavorful, and I cannot imagine a better meal after spending all day walking outside in the rain. The fries were super crispy and I liked the batter. My partner and I shared some of their breadsticks, which were deliciously baked (fresh!) and came with a super refreshing basil crema and a nice tomato-y dip. Wonderful all. My partner ordered fish and chips, and was surprised to find that it is one large fillet of fish, not multiple pieces like you would typically expect. He said the fish was fine, but a little tough. Overall, a wonderful experience. I definitely hope to return. I highly recommend this place as a refuge during the cold winter months!

    You know what I will admit that my ardor for The Observatory has cooled over time. I do still count…read moretheir rosemary pear martini as my favorite cocktail in town - and really their cocktail menu overall is still excellent. But the last few times I've stopped in for a meal, it feels like the food isn't quite as impressive as it used to be. Could be all in my head. Not sure. But it's always a nice spot to hang out and chat with friends, you can get seated quicker if you enter through Over & Out, which basically functions as an extension of the main Observatory, with it's own bar and pool tables.

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    Love the decor and ambiance
    Love the decor and ambiance
    Sesame Sweet Chili Glazed Chicken Wings ($12)
    Sesame Sweet Chili Glazed Chicken Wings ($12)
    Buffalo chicken salad (instead of a wrap)

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    Buffalo chicken salad (instead of a wrap)
    Someday

    Someday

    4.4
    (72 reviews)
    0.7 mi

    Dare I say it? Someday might be my second favorite spot to get seafood in Portland, right behind…read moreJacquelines - which if you know the cult following on Jacquelines in Portland, that is saying something. The ambiance is downright whimsical! Great wine selection, gorgeous floral installations, and one of those spaces where you immediately want to settle in with a book in hand. But let's talk about the crudo. I still think about that crudo. Bright, lemony, silky olive oil - simple but done so well. We even asked our waitress if we can keep the leftover olive oil to use it with the bread we ordered lol The oysters were also fantastic. They were barbecued, which isn't something you see every day. A little drier than a raw oyster, but still full of flavor. Limited seating so be sure to call ahead of time for a reservation if need be. This feels like the kind of place you celebrate something special, and honestly, I would not mind spending a birthday here at all! Worth it. btw the alleyway walking up to this place is so charming.

    what a kewt and quaint little spot!…read more the excel when it comes to building a nice vibrant, space for both indoor and outdoor dining. you can tell straight away that each of their cocktail drinks are thoughtfully curated and crafted - it goes without mentioning, that the staff can provide great recommendations if you feel torn between the options like we were. all in all, it was a great experience - and i can find myself coming back again whenever i'm in the hawthorne area!

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    My stinky, amazing Orange wine.
    My stinky, amazing Orange wine.
    Someday
    A cross between a Manhattan and an old fashioned

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    A cross between a Manhattan and an old fashioned
    LULU

    LULU

    4.5
    (158 reviews)
    1.8 mi
    $$

    Really solid cocktail bar! I loved my espresso martini and Hugo spritz I got…read more Ambiance was great. Perfect lighting balance at night. Ended up walking in on a night where they had a jazz band playing which was great. Bartenders were really nice. Good amount of seating. Street parking only.

    The IG videos make the food look delish but sadly the quality is not there. Bar service was super…read morefriendly and attentive. ordered the burger, calamari and vietnamese wings. Drink was a gin n tonic cocktail mix off the menu (can't recall the name) burger was basic, just meat, cheese and veggies, the meat was on the dry side - maybe 2 / 5 stars . came with fries, the fries were ok. calamari was great, light and crunchy, not a lot of salt - 3/5 stars Vietnamese wings - these were so disappointing, they came out hot and sweaty, there was a pungent gamey smell in each bite, the bone smelled foul also, either the brine wasn't great or they didn't clean the meat. the batter wasn't crunchy, just really soggy. not a winner like the sticky crunch wings at pok pok or like any other vietnamese restaurant that serves fried drumsticks and wings. not sure what was happening with the wings here but they were horrible - 1 / 5 stars, only ate 1 of 2 because of the funky smell from inside the chicken. had nothing to do with fish sauce either. overall, beautiful on instagram, is worth a visit for drinks but the food is lacking. in a foodie City like Portland that's just sad. I guess these are appropriate for happy hour menu items.

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    Hugo spritz
    Hugo spritz
    LULU
    LULU

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    Teardrop Cocktail Lounge

    Teardrop Cocktail Lounge

    4.4
    (1k reviews)
    2.9 mi
    $$

    To speak about Teardrop Lounge, I should probably start with this:…read more Ladies and gentlemen, I present my favorite cocktail bar. Not the best -- I'm not arrogant enough to claim that. I haven't been to every cocktail bar in Portland, and saying something is the best usually says more about your lack of experience than your conviction. But favorite? That I can stand behind. And I want to get that out of the way early, because of the amount of praise I'm about to pour on this place -- fully earned, completely intentional. The biggest crime here is that I only discovered it two weeks ago, after living in Portland for a year. It had been recommended to me countless times, and I ignored it. A mistake. A painful one. But now that I've found it, I don't plan on making that mistake again. I'm not typically an Old Fashioned drinker. In fact, I usually hate them. But somewhere between curiosity and too many episodes of Mad Men, I decided to try one anyway -- fully expecting to confirm my bias. Instead, it completely flipped me. Bright, almost citrus-forward in a way that felt unusual but entirely intentional. Balanced, smooth, just enough burn to remind you what you're drinking without overwhelming it. It was the first time I actually understood the appeal. I'm pretty sure I grew a few chest hairs that night. That alone would've been impressive. But it didn't stop there. The space is beautiful -- clean, intentional, but not cold. The staff are excellent: personable, engaged, and most importantly, authentic. Not scripted, not performative. The kind of people you actually want to talk to, and hopefully, eventually be on a first-name basis with. Now, all of that gets it close to a perfect score. But what pushes it over the edge -- what makes this place stick -- is the White Russian. One of the first drinks I ever had. My dad's drink. Not because of The Big Lebowski -- that came later -- but because it's just always been his thing. And at some point, it became mine too. Typically, when bars try to "elevate" a White Russian, they ruin it. They overthink it. Swap ingredients, tweak ratios, add unnecessary flair. And more often than not, it ends in disappointment. Teardrop does the opposite. They respect it -- but refine it. The coffee liqueur actually tastes like coffee. The heavy cream is properly integrated, not just dumped on top. The vodka -- whatever they're using -- is clean, present, and perfectly measured. There's a subtle complexity to it without losing what makes the drink what it is. It's the best White Russian I've ever had. No hesitation. I've gone back twice just to make sure it wasn't a fluke. It wasn't. If someone asked me what my death row drink would be -- this specific cocktail, from this specific bar, is in the conversation. Easily. Teardrop Lounge doesn't just make great cocktails. It reminds you why cocktails matter in the first place. And that's why it's my favorite.

    We came to Teardrop Cocktail Lounge while visiting Portland and were genuinely impressed…read more The cocktails were excellent -- thoughtful, well-balanced, and clearly made by people who know what they're doing. One of the best parts was how approachable the bartenders were. We asked for custom drinks based on our preferences, and both came out perfectly tailored. Creative without being weird, and strong without being sloppy. What really stood out was the price point. For the quality of cocktails, the prices felt very reasonable compared to similar craft cocktail bars in other cities. The vibe was also great -- relaxed, cozy, and not pretentious. It felt like a place where you could come for a special drink experience without feeling like you had to "perform" or order off a rigid menu. We liked it so much we actually came back a second time during our trip. Highly recommend if you're into well-crafted cocktails, friendly bartenders, and a laid-back but elevated atmosphere.

    Photos
    Custom Created cocktails by the mixologist!
    Custom Created cocktails by the mixologist!
    Filthy Vodka Martini from the local Timber Line distillery.
    Filthy Vodka Martini from the local Timber Line distillery.
    Late check out and Saturn cocktail drinks

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    Late check out and Saturn cocktail drinks

    My Way Lounge - lounges - Updated July 2026

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