One of our favorite rooftops in the city! A true Milwaukee gem that we enjoy as transplants! This rooftop is always a hotspot choice to enjoy some time with friends be sure to send someone ahead of time to grab a good seating location as spots fill up quickly. I also think recently they adjusted their pricing to give you a better value which is nice. The bartenders are always super helpful and there are good options for everyone. I will also say their food options and selections have increased tremendously recently. read more

On a recent short weekend trip to Milwaukee with my husband, we were staying at this Kimpton hotel and got to enjoy their wonderful rooftop bar, The Outsider. We were actually given two complementary drink beverages from the hotel staff for a reservation mixup which was appreciated and we took advantage of. It was a very cold Saturday afternoon and there was plenty of snow both on the ground and coming down. But the view could not be beat and the roaring fire definitely kept the covered patio space plenty warm. Our server was extremely kind and attentive. We had eaten a big lunch so we did not partake in any food but both of the cocktails we ordered were delicious. I ordered a tiramisu-inspired coffee cocktail while my husband ordered a pumpkin inspired old-fashioned. The drinks were strong and one was plenty to enjoy before an evening out. read more

The Outsider - Tiramisu-Inspired Cocktail and Pumpkin-Inspired Old Fashioned - Lounges Near Me - Milwaukee, Wisconsin

Came here for drinks after dinner and have always been a big fan of the ambiance here! We got to sit on a couch tucked in the corner and we had the espresso martinis, sooooo delicious!! Our waiters we had were great, continually checked in on us and made sure we were good. Will definitely be back for drinks again!! read more

The Outsider - Espresso Martini - Lounges Near Me - Milwaukee, Wisconsin

Cool place for drinks, chill upscale vibe, bathrooms are actually clean even though they're packed. Loved the drinks. Tried a few different ones. It's my second time here and both times staff was super attentive and fast to order our drinks. We came out for my daughter's birthday and they brought her a birthday shot for free with a little candle inside of it. I ended up missing it on camera, but it was still super sweet gesture. Definitely recommend coming here, especially in the summertime when they open up the patio. read more

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Five stars just for the space. This is a great rooftop bar! I can't think of a rooftop with better ambience. We stopped by on a Saturday evening and caught the sunset. There are plants and lights and heaters and a partial roof. Perfection! We had the old-fashioned, really good, but no cherry which was a little disappointing. We also had the spicy wings. They were good, crispy outside but not spicy. And we tried the walnut dip. It comes with crackers, cucumbers and carrots. It was fine, but nothing to dream about. The service was a little slow, but our server was sweet. She might have been new to the job. The people we were with assured us it's not normally like that. Go for the atmosphere, your won't be disappointed. read more

The Outsider - Rooftop sunset - Lounges Near Me - Milwaukee, Wisconsin

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Great spot for a cocktail with excellent city views. Nice outdoor seating and variety of options. Cocktails were tasty, like how their specialty cocktail menu changes. read more

The Outsider - Frozen Framboise Sherbet Pink Cloud Summer - Lounges Near Me - Milwaukee, Wisconsin

This is a good rooftop place to grab drinks with your girls or a group. I liked the outdoor seating with the fire pits that are perfect for chilly nights. The drinks were good but overpriced for the taste which was average. Service was good but it felt like the waiter kept wanting us to buy drinks and was circling around by our table too much. read more

Delicious drinks and great views of the city. If you can grab a seat by one of the fireplaces, you can cozy up for hours. A unique twist on the espresso martini! Never had a drink here I didn't like. read more

I got a frozen cocktail and an appetizer of fries. Frozen cocktail was strong! Fries were tasty. The view is practically unbeatable during the sunset. Def recommend for an elevated experience. Service was quick and attentive. read more

Went to The Outsider recently for a surprise birthday party. This was my second time visiting but it's been years. I gave them a 4-star rating because while the ambiance/vibe was a 5, the food and drinks were a 3. The staff did a great job of waiting on our party of 20+, making sure we we had water and could order. I personally had a mojito - my go-to drink - after learning that their house cocktails are pre-mixed, which was the first red flag. The mojito ended up being very sugary like it was loaded with an artificially-flavored mixer. The food was meh too: undercooked wings with delicious but pricey $12 fries. I'll certainly go back, because the vibe is unmatched but on a full stomach. read more

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The perfect rooftop bar! This our go-to spot. The atmosphere is fun and the views of Milwaukee are great. The drinks are so nice and it's relaxing to sit by the fire. Indoor and outdoor seating, so perfect for both winter and summer months. I have been here several times! It is usually pretty busy, but there is also a lot of seating. Highly recommend checking this place out! read more

The Outsider - Lounges Near Me - Milwaukee, Wisconsin

We came here for cocktails before dinner, and there was absolutely no third Ward parking because of the art festival. Bummed that we finally found a spot and the rooftop garage doors were closed. Still cozy vibes with the fireplace and couches, and very prompt service. I decided to try a happy hour drink - the "TEA SESH" only $10 for "JEFFERSON'S BOURBON, PEACH TEA SYRUP, LEMON, HONEY, PEACH BITTERS." Very refreshing and a light bourbon drink. My fiancé got the frozen Framboise Sherbet (the raspberry frozen drink with blanco tequila, oat milk, orange and lime juices.) He really enjoyed his too, and lovely presentation. Always love the outsider, and you MUST try the new beer battered cheese curds. To die for! read more

The Outsider - Lounges Near Me - Milwaukee, Wisconsin

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The rooftop views were amazing and the space had a chill, open vibe with plenty of seating. Great spot for apps and drinks, we had the cheese curds (my first time trying them) and they were super good. Drinks were fine, nothing fancy but solid. Only downside was the service. It took a while for anyone to come by, even for menus, and another table that came after us got served first. My cousin had to flag someone down to get our order in. Other than that, it was a nice spot overall. read more

Always love coming here but don't come often due to the high prices. Was there yesterday and I ordered a margarita and it was $19, just a regular reposado margarita $19. It wasn't even a special cocktail from the menu. I've been to NYC, Boston and Chicago and never paid that much for a regular margarita! I really think they need to re-evaluate their pricing on drinks. read more

Stopped by the outsider on a Friday night with some friends. It was a terrific vibe and was quite busy. We luckily nabbed a table when some folks left, but there was definitely no seating available or really anywhere good to stand around. Both bars were packed as well. I got the violet hour which was good but not as good as previous visits. The bar was also a long wait but we eventually had a server who was fairly quick. I'd definitely stop by here but know that finding a table is a game of chance read more

A solid place for drinks, vibes, and views! A bit on the pricier side but you're definitely paying for the rooftop experience. I went in the spring while it was a bit chillier outside, but they had enough warmers where we were sitting that I felt very very cozy. I'm looking forward to coming back in the summer to experience the open patio! read more

The Outsider - Aperol Spritz - Lounges Near Me - Milwaukee, Wisconsin

The Outsider is one of Milwaukee's best rooftop bars. The service is usually spot on. And, they don't offer your everyday bar food. You can get chicken karage, spam masubi, and other bites here at the Outsider. I highly recommend that everyone ventures out here in the Summer months. The view and clear skies are to die for. The Outsider is perfect for groups. You can have a solid group of 4-9 people seated at the Outsider. The outdoor seating is very comfortable and there's little fire pits scattered throughout the rooftop. read more

The Outsider - Lounges Near Me - Milwaukee, Wisconsin

If you want a nice vibe, with good music and bar bites and view overlooking the city then this is the place for you. It's definitely a spot to get dressed up and enjoy your evening. The bar bites are delicious and the service is great. This is my favor rooftop in Milwaukee. read more

The Outsider - Bar area - Lounges Near Me - Milwaukee, Wisconsin

Great bourbon choices... secondary prices for sure but they had a great roster of choices. If you want a mixed drink, don't feel limited by the menu, the bartenders are experienced and responsive. They made great drinks. Beer options are few but that's ok... you get pilsners, IPAs and domestics so you're good if that's what you like. I was a bit surprised at the electronic dance music thumping but the crowd was ok with it. Great views and rooftop area. read more

The outsider is a great rooftop bar with beautiful views, outdoor fire pits, and is perfect for a drink with the girls! Our bartender, Aaron, was so helpful and very fast despite how packed it was in there! Give him a raise! The food was delicious, I highly recommend karaage chicken, it was so crispy and came with the BEST sauce I've ever had. We also got the rice cakes and they were good but I don't think I would order them again. read more

Such a vibe! This spot is perfect for grabbing drinks in the winter - cozy, warm, and full of energy. I loved how the top 40 hits kept the mood upbeat all night. We tried a few dishes, but the crispy rock shrimp and karaage chicken stole the show - absolute favorites. As for drinks, the frozen cinn-a-roll? Chef's kiss. It was the perfect sweet treat to wrap up the night. Definitely recommending this place as a go-to nightcap spot! read more

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Nice atmosphere! There was a DJ playing when we went which was really cool. The drinks were good. It was packed and there was an event blocking off the outdoor seating, but overall it was a great vibe. read more

The rooftop was extremely busy last night, but it was a Saturday so it makes sense. It was crowded, but still enjoyable. I decided to go with a lemonade for the night. I'm participating in lent, and I just wanted to have a good night. What they do have is a fair amount of mocktails available. I can't wait until it's warmer out and they open up the outside section and have it available for people to enjoy! read more

The ambiance is excellent here. There is wonderful seating and very good service. The food is decent. The staff is okay, they are attentive enough and none of them are openly rude or dismissive which is pretty nice as well. However, probably because this restaurant is so beautiful and on a roof top, the drinks are quite expensive, so if you are looking for something cheap to do, this is not where it is at. I've really enjoyed all the experiences I have had at this bar, so I would recommend going for the views. Of note, there are quite a few business meetings or business adjacent meetings I have overheard at this bar so this might be something that you end up experiencing. read more

The cocktail bar we'll keep coming back to! My girlfriends and I were out on a Saturday afternoon, and one of them suggested The Outsider for some drinks. Despite being the dead of winter, this rooftop was sooo enjoyable. It may have been a cold day, but it was sunny and here they keep their rooftop patio open but enclosed, if that makes sense. You still feel like you're enjoying the outdoors while sitting inside, as the clear coverings and glass ceilings let in alllll of the light. We grabbed a high top and were quickly greeted by a really friendly face. She brought over menus and grabbed us waters while we browsed. I convinced my friends we had to all get espresso martinis because we'd never tried them here (and they're the best drink ever). Not the best one I've ever had, but still tasty. They came in a smaller/different shaped glass than a typical martini but I liked that! We changed it up afterward and got ourselves various other cocktails - all super enjoyable. Big fan of the botanist drink, with clove and rosemary infused botanist gin and blood orange honey syrup. I've come to learn you really can't go wrong with any drink choice you order here. There's nothing they can't make you. As for the atmosphere, ambiance and decor... what's not to love? read more

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It was raining when we went to so it was closed to outside but they still had the fireplaces going and it was just a great cozy vibe. I like to go for the featured cocktails whenever I try a new place but there weren't many I was confident I'd like because I'm really a fruity, don't want to taste the alcohol type. But I tried the espresso martini and was pleasantly surprised. I've had one somewhere else before and it was overly bitter and very alcoholy tasting. This one was definitely espressoy but not overly bitter and just very smooth. I'd definitely order it again. Highly recommend this a great date night spot. read more

The Outsider - two cocktails on a table - Lounges Near Me - Milwaukee, Wisconsin

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Beautiful space but rarely any seating. Very young atmosphere for an old folks hotel. $17-25 drinks is unacceptable in Milwaukee though. So I paid $20 for a Moscow mule but there was no copper mug. Wtf, I just moved back from SF and the Moscow mules aren't even that expensive there. The Outsider is highway robbery with a good view. read more

I'm really not sure why I haven't reviewed The Outsider before now, seeing as I have been here dozens of times. But saying that should give you some idea of how much I enjoy this place. The Outsider is a really solid spot for an evening out. It is located on the rooftop (9 floors) of the Kimpton Journeyman Hotel. You will have to enter the hotel to get here, but hotel staff are very used to directing people towards the elevators that lead to The Outsider. The space itself is wonderful - great views of the city, a variety of seating options, lots of comfy couches, and a large bar area. The Outsider is open year round. Even in the dead of winter, they manage to keep the majority of the bar open with the help of heating lamps. The Outsider has an extensive drinks list. You will find your typical fare here - beers, wines, typical rail drinks, etc. But there is also a list of house-designed cocktails. These drinks are seasonal and are inventive and enjoyable, although quite pricey. In fact, I would say that The Outsider is generally one of the more expensive bars in the Milwaukee area. You are certainly paying for that rooftop view. For the cocktails, the price point feels fair, as these drinks are very nicely presented. But the price point is certainly quite high for the beers and wine. A couple things to make note of: -The Outsider on a weekend in the summer is going to be insanely busy. Come prepared -People usually come dressed in nicer clothes. There is no dress code officially, but you won't see many people in sweats here. -Service is a bit varied. Sometimes the servers will come to your seat to take your drink orders. Other times, you have to go up to the bar yourself. I think this is largely dependent upon their staffing and how busy the bar is on that day. read more

I always have a good time at the outsider. Been there several times for a cool lounge vibe and drinks. The drinks are delicious, the menu has a wide variety of options which is very nice. It is on the more expensive side, but that's what you're paying for for the rooftop view and location. Good quality as well. I've always had good experiences with the wait staff and bartenders. The place gets very busy on the weekends, so keep that in mind! read more

This place is all about looks. Great view and a good time. Waitstaff is sweet and helpful. We got a handful of cocktails and they were pretty good. We also got the popcorn and it was plain and a waste of money. Still had a good time and would recommend...just wouldn't get the popcorn. read more

The Outsider - Lounges Near Me - Milwaukee, Wisconsin

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My group had a fantastic evening filled with laughter and GREAT food at The Outsider. Our ongoing joke about needing to order the rock shrimp added to our fun. The shishito peppers with spicy vegan aioli and sweet tamari reduction was an exceptional starter. The seasonal menu showcased carefully crafted worldly flavors. My drink, the Honey Cat, featuring Tom Cat Barr Hill gin, grapefruit, lemon, honey, and chai liqueur, was a surprising delight. Who knew chai and grapefruit would pair so well? The attention to detail in the drinks mirrored the overall quality of the experience. The cozy ambiance, complete with fireplaces, made the rooftop setting perfect for a night out with good friends. Our server was also great and outgoing. I loved her shoes!! I can't wait to return. This place is so cosmopolitan. read more

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The Outsider is only good for the ambiance and views. It's very cute, and I love the fire pits, but good luck finding seating on a nice day or on the weekends. The drinks are not worth what they charge at all. They pour literally one shot and fill the glass with ice. Service is alright. I've definitely come across bartenders with bad attitudes. You'll only catch me here if my friends want to go here. It won't ever be my choice. read more

Pricey but nice. We stopping in for a cocktail after a few recommendations from friends in the area that if nothing else, it was worth stopping in for the rooftop view. In the end, I got to enjoy a fancy cocktail on a rooftop above the city and that fulfilled my needs and expectations. We were seated at an outdoor table, and we had table service from a server. I am pretty sure you could also order for yourself at one of the bars and walk around and sit with your drink somewhere, especially if it was as not-busy as it was when we were there. They do have a small food menu, but we opted to get our meal elsewhere and try more places. But you can eat with your drinks here. The drinks were tasty and there are worse and uglier places to sip on a beverage than the outdoor rooftop deck at The Outsider. read more

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The environment is nice, staff are friendly when they are serving you, otherwise nobody will talk with you. It is hard to find a place to seat. Expensive food and drinks, because of the area. Cocktails were ok. read more

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One of the best roof top bars Milwaukee has to offer! It's especially nice in the summer. The outdoor area has plenty of seating and fires to keep warm during the cooler evenings. It's a classy place but not too fancy to stop by for a casual drink. Their frosé in the summer is the best! The espresso martinis are great as well! The bartenders are all very nice. read more

The Outsider - Lounges Near Me - Milwaukee, Wisconsin

Great rooftop bar, drinks are pricey, but you're paying for the view as much as you are the cocktails. Seating can be tough on busy nights, but overall a good spot for a special occasion if you can plan ahead. There's nowhere else in the third ward where you can get the same view. read more

Wonderful lounge with comfy sofa's, cushion's blankets throughout and around fire pits. There are planters with modern birch tree arrangements sheared at the top. The roll up garage doors when opened in the summer I can imagine makes for wonderful outdoor seating overlooking the city. Staff is very friendly, especially host and Kevin our server. Very attentive, personable and timely. Though my wife only ordered the fried rice cakes, she said they were amazing and will definitely have them again on our next visit. Definitely worth a look, have some drinks and wonderful food. Highly recommend!!!!!! read more

Unfortunately this was recommended to us for (1) dinner and (2) its non alcoholic options. First, we knew there was a problem when we couldn't even find it. It's the top floor of the hotel but we saw no signage for it. It's not really a restaurant. It's a bar. There aren't even dining tables. They do have food, and the two of us were able to get our fill with three of the small plates - the brisket buns were good, the popcorn chicken was...chicken, and the fries were fries. Dips were good but nothing spectacular. And the NA menu (one of the reasons it was suggested for us) consisted of only two options. $13 each - when the alcoholic cocktails were $16. In the end, three small plates, and NA and a glass of wine were $75 before tip. It didn't help that it was winter - most of the areas were too chilly to enjoy on the patio and even in the regular bar area we had to keep our coats on. It was fine but didn't justify the price tag. read more

Best city views, great for locals and out of town guests. I LOVE coming here. I just left there and saw an authentic Puerto Rican holiday cocktail on the drink menu!! Could not believe our eyes!!! Although overpriced, we got it anyway- I mean, you NEVER see this on a drink menu downtown. It was perfectly flavored, in an authentic bottle. Big props to the mixologist. No label on the bottle so assumed it was house made.. great job ya'll! Puerto Rican Coquito @Outsider! WEPA!! read more

The Outsider - Out with friends who also loved seeing Coquito on the drink menu - Lounges Near Me - Milwaukee, Wisconsin

We came here on a hot sunny Sunday afternoon for some drinks and it was exactly what we needed. Everything on their new summer menu looked so good and was so hard to choose! I eventually ended up picking the Watermelon Shuga and my husband went with Feelin' Peachy. We both loved them! Mine came frozen/blended and even though it melted quickly under the summer sun, it did not lose flavor at all. The sugared rim was the perfect touch. I also sampled the Feelin' Peachy and I think I preferred this one just ever so slightly more, but I let my husband keep it. Both drinks were very refreshing! The rooftop is the place to be, the music was pumping, and the service was great. We have never been disappointed here and will be back summer or winter! read more

The Outsider - Feelin' Peachy - Lounges Near Me - Milwaukee, Wisconsin

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