Generations At Five Points

We dream about this place! The food is so unique and wonderful! I love their constantly changing menu. The menu creator has to be a pure genius! Definition of genius: A genius is a person who displays exceptional superior intellectual ability, creativity, or originality, typically to a degree that is associated with the achievement of new advances in a domain of knowledge. We drive over an hour just to visit here on special occasions. Move to IL please :)

The food here for dinner is good. I’ve already reviewed that.
But I was BLOWN away by the brunch menu! A friend and I met here to test out the new options for brunch on a Sunday. We both had a Bloody Mary (complete with mini grilled cheese sandwiches!). We opted to split the eggs benedict and the blueberry pancake. The Benedict was good. Eggs poached perfectly, delicious hollandaise sauce. Best part? Served on a biscuit. Which led us to ask why we aren’t serving more things directly on biscuits?!
But the holy grail, the best of the best, the item I am STILL thinking about and trying to find everywhere I go for brunch/​breakfast — the blueberry pancake. First of all, to call this a pancake is an immediate injustice. It’s better than a pancake. Some sort of mix between a muffin and a cake and a pancake. It’s got a crispy exterior from the skillet it’s baked in and a moist delicious cakey interior. It’s been over a month since our visit and we are STILL talking about that pancake.
Added bonus? The brunch menu is incredibly affordable. Most entrees are plenty of food for one but come in somewhere under $ 10.
Well done on another menu.

The brunch menu is wonderful. Had the duck panini and it is amazing. The pancakes are wonderful and thin now. Great service which is why I am changing my rating to 5.

Everything is flavorful. Each item brings out a new taste. The menu changes monthly yet the favorites remain. The owners are attentive to details and very customer oriented.

They tout «everything fresh» but the mushrooms were canned, tortilla chips from a bag, buffalo sauce pre-​made, and cheese on nachos from a sauce can. Bartender is a little slow but wow can he make an awesome drink. I actually will be back for him! Sad they no longer have live music, so the quest for a good place to eat with live music in Waukesha continues!

My wife really likes this place, I believe because of the ambiance. I say so too, and enjoy the menu variety, but at the end of the day the experience is in my opinion not reflective of the higher pricing. I know Waukesha needs more places like this, but we’re talking about Downtown Milwaukee prices. Maybe I’m just being hard though. The service was not upper crust, but regular (server not knowing all menu items or to mention specials, brought tapas but no silverware). This of course is fine if paying less. All in all, go to Generations if you out in Waukesha in your nice clothes. If not, try People’s Park or Mainstream.

Chicken lettuce wraps will blow your mind! Great place for date night or if you love trying different things!

I’ve had really great dining experiences here, and some «just okay» ones. I ultimately keep coming back because the food is great and the bar has some interesting cocktails available.
The menu changes often (including the drink menu). Seasonly they have different dishes on the menu, and even special menus for weekends like Valentines Day. The food really is fantastic. Dessert is amazing. Their menu features a lot of gluten free and vegetarian options.
What bugs me about this place is the pacing of food. Sometimes you get food delivered right away, sometimes it’s only a few people served first and others in your party have to wait 15 minutes to get their dish, and sometimes it’s a toss up. I am not quite sure why that’s the case here. The servers are always attentive and friendly — but why can’t the food be served at the appropriate times?

We went there last weekend after over a year away of this being one of our favorite west side restaurants. We had heard some rumor they switched from tapas to a mostly-​pasta-​dish menu and stopped going, but, at least now, that is no longer true. There are some pasta dishes on the menu but it’s mostly small plates, as creative and delicious as we were used to. Some of the favorites, like the root beer braised short ribs were gone, but plenty of good replacements were to be had. We will definitely be going back! So glad we finally decided to check the menu and realize our mistake on the pasta.
I don’t know what the service complaint so many people have on here is all about. We were in and out in just over an hour (not rushed by anyone — we had a movie to get to) and at no point did I think the service was slow or poor. We mentioned something to our waiter and he said they had just changed over almost the entire waitstaff in the past month, so maybe the old waitstaff was bad but based on our recent experience I wouldn’t complain at all.
Overall, this is a great place to dine. I’m giving it 4 stars because I think in the Milwaukee area in general you can do better, but if you’re near Waukesha and looking for something a bit closer to home, this is easily one of your top options. Good flavors, unique food, decently priced.

This place is, for me, consistently good. I love the tapas to share, the new homemade pastas are a nice addition to the menu, and the ambiance in here is very nice & different from other downtown Waukesha spots. It’s VERY GF friendly, too, which is a plus; I always take family here when they’re in town, as we have some dietary restrictions. They’ve always been very accommodating. I love the lettuce wraps, the goat cheese, and I’ve enjoyed almost every small plate I’ve gotten here. The menu changes monthly to keep up with seasonal flavors. I definitely recommend and the prices are reasonable, too.

When I first walked into this place I was pretty impressed. It has the décor and ambiance of a hip Chicago type place, but only difference is that it’s in Waukesha. I sat there in total joy thinking; «Wow, I so can’t believe that there is a eatery this cool in Waukesha». Well I got knocked out of dream land real quick and the reality of being in Waukesha knocked me upside the head like a moldy old cheese head hat wrapped in a Bret Favre jersey. Oh but please forgive me, I am really stretching the truth here, because it didn’t happen «really quick». In fact, nothing here was quick. It took one hour for our food to come. Yes one hour! It was like a really bad episode of Hell’s kitchen, and unfortunately Chef Ramsey was no where around to yell at any of the people working in the kitchen. But it just wasn’t us, I looked around the room and no one was being served. Thank the Lord that their incompetence was bestowed upon everyone and not just me or I would have left with a complex.
And when entrees were served, I saw tables with 4 people at them and only one person getting their food. And I guess who cares, but it looks a little lame when it’s a family of 4 and the dad gets his food and the poor kids are still sitting there starving. And even lamer was the fact that they had been there before me, so they were there for even more than an hour. There is no excuse for this. I so don’t care if it was a Friday. You plan for more customers on the weekends by being adequately staffed and organized or you will soon find that you have no customers.
Now if this were an episode of Hells Kitchen, the show starts out with the service being really slow and the customers getting frustrated and upset, but then once the food is served all is forgiven because the great delicious entrees make up for whatever issues occurred in the beginning. Oh yes, and that was exactly what happened here. NOT!!!
The cooks here have sooooooo much to learn about Tapas. Maybe they are banking on the fact that people around these parts will have no idea of what a tapas is, so they can just serve slop and no one will be the wiser. Well they thought wrong again. The food here is just god awful terrible!!! And I’m not just saying this based off of one entrée but based off of 3 tapas selections. We started off with the Baked Brie, all I can say is totally disgusting!!! The actual Brie had something on the inside of it that resembled the appearance and consistency of snot. And I couldn’t quite understand why they had the apples and roasted peppers on the outside of the Brie instead of cooked on the inside. I’m telling you right now, they need to go to some real Tapas places and see out it’s done. Who ever the cooks are in this place totally lack creativity. No real chef would have ever served a tapa like that, and I’m using the term chef and tapa here lightly.
Next we had the seafood biscuits and gravy. «Oh LAWD, what have I done to forsake you???» More slop. Chewy shrimp that was half cooked to the point that I could do nothing but spit it out and it was drowning in some sort of questionable looking orange colored sauce. The biscuits were ok, tasted like out of a box.
Then lastly we had the Lettuce wrap. Now my husband thought this entrée was good. I on the other hand wasn’t impressed. I agree that it was much better than the other 2 disasters but that isn’t saying much. At best this dish was average. The filling for the wrap had the appearance of dog food, but I was so hungry at this point that I ate it anyway, and dog food was definitely a step up from what they were serving.
I noticed that at several tables people were sending food back. Oh what a downward spiral for this kitchen. They were really, really, really behind and I feel that they just started to send out food in a half-​assed manner just to send it out. And that’s no good especially when the food is not much to speak of in the first place.
I’m being really kind here when I give this place 2 stars instead of the 0 stars it deserves. And I’m doing this because I really want this place to make it. I give the owner total credit for attempting to have a restaurant like this in Waukesha. But just because you are in Waukesha don’t half step on the quality. I believe this place has some potential, so because of this child like optimism I have, I will give it one more try. And will update accordingly. BTW Real Tapas restaurants give patrons clean utensils when new entrees come out, dirty plates and forks won’t make it taste better.

The menu has changed for the better since this place first opened. Now offering tapas as well as full meals was a great addition. The food tastes fresh and the flavors are excellent. Portions aren’t overly large, and I love leftovers :) Live music on the weekends is always nice and the ambiance is really appealing.

I coordinated an event for my mom’s graduation at Generations. I got in contact with Jeff, the chef and GM, ahead of time, and he completely delivered on an awesome customer service experience.
Dealing with us wasn’t totally easy since I didn’t know the number until about a week beforehand and because everything had to be gluten free. Jeff was accommodating and awesome.
Not only was the customer service awesome — the food was so good! The lettuce wraps, the root beer braised ribs, the margarita and pork sliders, etc. etc. — all so good and our guests loved everything.
Living in Minneapolis, I’ve become a little bit of a food snob. This little gem in Waukesha totally delivered and more. I’m so glad we chose Generations for our event. The service, food and organization were great.
Visit now!

There’s not a lot of good, non-​chain dining in Waukesha, but Generations really brings it. I’ve never eaten in the dining room and have always opted for a high top in the bar. The staff is very friendly and the drink prices cheap (Rehorst specials!). I’ve always enjoyed the tapas plates we’ve gotten there and they’re great for sharing with a group. I don’t drive out to Waukesha to come here, but when I’m looking for a dining place in the area, it’s always on the list.

I just can’t picture it. I can’t picture a scenario in which I would ever again, while trying to decide on dinner, say «Let’s go to Generations.»
I would like to just start by warning anybody that’s pregnant or Baptist, this is not the place for you. Your non-​alcoholic drink choices include: skanky Waukesha city tap water that smells like the wrong end of a gym sock, or you can have some powdered lemonade mix (made with aforementioned sock-​water). That’s about it. Or soda (again with the sock water).
So the nitty gritty:
The baked brie was just ok. Maybe not even that good. It seemed confused and disjointed… Grilled peppers and grapes and candied pecans… Pick a direction and go with it.
BBQ pulled smoked pork was kinda dry, and not smoky enough for my taste. I’m picky about my BBQ, and this didn’t measure up.
The worst dish of the night was the fried chicken, which tasted like thin strips of overcooked breast meat dusted in plain flour, fried and drizzled with honey. This I can do at home, and it would taste a lot better.
But get this: we informed our server in plain English how we were not satisfied with the chicken (and lemonade, for that matter) and we still ended up paying for both.
Please, somebody renew my hope in Lake Country, Wisconsin. There has to be a restaurant with good food, service and atmosphere all under one roof… Why haven’t I found it yet?

Wonderful Greek chicken flatbread here. Wouldn’t get anything else. Flatbread is warm and toasty. Chicken still moist. Veggies all fresh. Feta abundant. Would never turn down a lunch here.
3 stars why? Something about this place doesn’t «feel» right. Maybe it is the glowing «Cocktail“esque bar. Maybe it’s the comfortable lounge chairs on wheels. Maybe that every décor item seems vaguely familiar because I’ve seen it at TJ Maxx Home Goods. (PS, that is not a dig, I love Home Goods) Maybe it’s the fact that despite being high noon in a clean, reasonably priced restaurant we were the only ones there. Stupid reasons to downgrade a 4 star restaurant to 3 stars? Maybe… probably.

Some of the best thought out food you will find in downtown Waukesha. Some dishes can be misses, however the hits more than make up for them.
Be warned, they switch the menus monthly, so if you have a favorite it may not be there the next time you visit.
I had been in a couple weeks ago and ordered a late lunch. I ordered a coffee with my lunch and they came back and said they were brewing a fresh pot and it will take a bit longer… The shocking thing was… we were the only ones in the restaurant at the time! I love that!!! Nothing is worse than being served a cup of burnt overcooked coffee! Small things like these show that this place really cares about the quality and standards of their food.

This place looks really nice when you walk in, but once you get a table, just wait. And wait. Because the servers are taking their time.
I have been to Five Points on a few occasions, always toward the end of the dinner rush (around 8), but long before close — while several servers are still on the floor. Once my group of three finally received our food (lettuce wraps, teriyaki chicken, artichoke bottoms and pot stickers), all of it was salty and tasted prepackaged. There was nothing fresh about it. I don’t mind asking for water because I know some people won’t drink it, but after we asked for a round, our glasses stayed empty through most of our 2-​and-​a-​half-​hour visit. With the salty food, that just wasn’t enough.
I won’t be back.

We had a great night at Generations. We ended up staying after dinner to listen to a great band in the lounge.
The wine list was fantastic… yep, had 3 bottles.
The only reason I give 4 stars instead of 5 was that the salmon dish was terrible… overcooked and dry with a strange chili sauce. Otherwise, all our dishes were great, including the goat cheese, mussels, and shrimp. We didn’t have any meat dishes because one person was observing Lent in our group!
The atmosphere was okay, with a modern cool vibe. The dining area was okay, but not particularly quiet or inviting. The lounge chairs in front were awesome for relaxing. They just need more of them!
I would definitely recommend this place for a fun night out with a group of friends. The fab music was an added bonus!

Moderate food, zero atmosphere and overpriced. Can’t imagine going back on purpose.