Wow these are some great ideas! A lot of these did not pop up during my previous quick google of things to do, so I really appreciate the variety.
Rock on the Hill looks… interesting. We might stop - it wouldn’t be too far out of our way leaving Madison for Kansas City.
Any restaurant suggestions for Milwaukee or Madison?
MKE has a big central/eastern european heritage: Great german food at Mader’s on Old World 3rd St. along with wonderful serbian food at 3 brothers and Old Town, Polish food at Polonez.
But it has TONS of other great restaurants. What sort of cuisine would you like?
I haven’t lived in Madison since 1989, so I’m sure that most of my favorite places are long gone, but when I went to find some lists of “best restaurants in Madison,” I found this article – the #1 place on the list (Oakcrest Tavern) is literally next door to my last apartment in Madison! 
About 45 minutes outside Madison is New Glarus brewing. They have a great brewery situated on a hill and having a tiny tinge of a Willy Wonka kind of feeling to it – at least to me – and the town itself has this Swiss theme to it that is kind of fun in a cutesy-Americana sort of way. Whenever I’m up in that direction, I like stopping by there.
If you like a little bit of kitsch, Madison – or rather, Middleton – has the National Mustard Museum.
In Milwaukee, I enjoy the pizza over at Maria’s and Zaffiro’s. Maria’s serves these idiosyncratic giant oblong cracker-crust pies that I haven’t quite had anywhere else. No alcohol there and the place is decked out in religious Christian imagery. Zaffiro’s has a more typical pizza pub atmosphere and some of the thinnest crackliest pizzas I’ve ever had.
If you feel like your blood cholesterol needs a boost, check out Solly’s for their butter burgers. They put on a metric shitload of the stuff. Your plate will be dripping in golden grease. A more sensible option may be the local chain Kopp’s where you can get a butter burger with a frozen custard, an area treat.
If you are all into ice skating, the Pettit National Ice Center is there, and one of the few places where you can skate around an Olympic-sized 400m speed skating oval.
Those look great! We’re coming out of Oklahoma, where fresh cheese and Northern European food are fairly unusual The one food I definitely want to find are fresh cheese curds.
I’m a pretty adventurous eater and definitely want to try cuisines/foods that are area specialties. So things like the regional pizzas and burgers that pulykamell suggested are great too.
This is a big Yes vote for House On The Rock (since most of the other posters have been rather disdainful. There’s a website that reviews American Roadside Oddities, and they rate House On The Rock as one of the two finest in the land (along with the City Museum in St. Louis).
There’s so much there that it’s eventually exhausting, but my family found it fascinating. It can fill up as much time as you want to throw at it — the “2 to 3 hrs” figure that one poster gave seems like the basic time to stroll through without studying anything.
As someone who loves road trips and roadside attractions, House on the Rock has been on my bucket list for awhile. I had been planning to head out there in a couple of weeks, but the smoke and air quality reports have me reconsidering. The aspect of a multi-week journey with the horizon obscured by haze and smoke just doesn’t appeal to me.
Fresh cheese curds are the best, and are usually obtained directly at a cheese factory, where they’re really fresh. When fresh and warm, they squeak when you eat them. The Cedar Valley Cheese place I mentioned upthread generally has fresh samples of them on the counter, or at least fresh bags available there.
Otherwise Wisconsin Cheese Mart, right across from Mader’s german restaurant will have them, along with some elder cheddars. That’s where I once procured some 30 year old cheddar. They also offered some 42 year old cheddar at that time, but I couldn’t get any before it sold out.
I’m from Milwaukee, living in Madison, and love both towns. I’ll add more later, but don’t leave Milwaukee without seeing the Art Museum… it has wings that open and close depending on light and weather. There’s a great restaurant, The Harbor House, with a great view of the wings, next door (both are on The Lake… Lake Michigan is wide enough that it looks like an ocean).
Just south of there (just past the Summerfest grounds*) is The Third Ward. Hipsters rehabbed a whole neighborhood, and there’s a Belgian Ale House (Benelux), a local brew pub (The Angry Hop), and the Milwaukee Public Market (a tiny Pike Place Market), with a spice shop, clothes, ethnic food, coffee, bakery, and… great lobster rolls.
*Summerfest does get crowded, so I go early afternoon on a Thursday… no crowds, no drunks, just walking around… very fun, as are all the food vendors. Get there hungry!
Regarding House on the Rock, I usually say it’s worth talking a walk through it if you’re in the area and have the free time, but it’s not a destination. I wouldn’t make a day out of. That’s why I mentioned upthread that if you go to Taliesin, it’s worth going to HOTR (they’re only 10 minutes apart), but I wouldn’t stop at Spring Green just for HOTR. You’d be better off hitting The Dells for a day. Do some Go-Karts and spend a few hours at Noah’s Ark.
Same here. I’ve never been there despite it being about a 10 minute drive from where I’m sitting right now, but I’ve not heard a bad word about it. The attached restaurant is supposed to be good as well. As in, it’s popular on it’s own, a lot of people eat there without going to the museum.
And, just to say it again. The Milwaukee Public Museum is really, really good. If you have kids, they’re all but guaranteed to enjoy it.
Just an FYI, I believe they’re closing. They posted something on facebook quite a while back about remaining open until they can find a buyer. However, I can’t find the post at the moment to confirm it and I don’t recall if the intention is to find someone to buy the restaurant and take it over or buy the building and do whatever they want with it. Another place I’ve yet to visit, though the owners shop at my store.
Also, assuming you don’t get to the Cudahy/St Francis area that often, Semanos is closed as well. When it was for sale, they had a few dozen interior pictures of, not just the restaurant, but the two (residential) floors above it. I was surprised at big it was.
Solly’s, the place where the butter, very literally, drips off your elbow while you’re eating.
I’ll second/third/forth Kopps, as I always do in these threads. I’ve been there twice, just this week.
Most cheese curds you find, at least around here, will be fine. Especially if you let them sit out for a while to come up to room temperature. But actual ‘fresh’ ones are even better. These are the curds that were made that morning and have never seen the inside of a refrigerator. Malcore is a popular brand of fresh cheese curds. Wherever you go, ask if they are fresh from that day. My store gets cheese curds in from them every Friday (I think it’s Friday), so, in that case, if you got them any other day, they’d be more like normal (but still good) curds.
Considering it may be the only time you’ve had fresh curds, might as well go all out and get the squeakiest ones you can find.
…cheese curds squeak when you chew them. Did you know that or did I spoil it for you? I didn’t know it the first time I had one.
ETA, I see QtM already spoiled it for you.
Ahh, THE place for squeakiness* is the Madison Farmer’s Market.
Note: with all the free samples at the market… the OoeyGooey Cookies, the beef/bison/ostrich sticks, the chips ‘n’ salsa (AND the Spicy Cheese Bread!), you may not have room for your late lunch at Marigold (best “organic/classy” brunch food), Cooper’s Tavern, or The Old Fashioned. All on the Capitol Square.
*And keep in mind we’re talking fresh naked cheese curds, not the deep fried cheese curds (also worth trying).
Go to Baumgartner’s in Monroe and enjoy a Limburger sandwich. Limburger is made at only one place in the US, and it’s in Monroe, WI.
Ooo… I second the nomination. I go full bore and get a Limburger and liverwurst sandwich. The beers ar local Minhas brewery (if it’s still there) aren’t the greatest, but the tour is not stingy on the samples (or at least wasn’t the last two times I was there), so it’ll give you another thing to do in Monroe.
Qadgop wonderful food and cheese recommendations! I’m not sure about Limburger, but I will be trying to find some aged cheddar.
Okay I love the City Museum in St. Louis - I’ll definitely check this out some more.
Joey_P I had heard several years ago that fresh ones squeak and have sought some to no avail! Surely Wisconsin won’t let me down 
The days we will be in Milwaukee the art museum will be closed. I had seen photos of it before and really wanted to visit, so definitely a bummer. But good news about the Third Ward - we’re either staying in it or just outside of it.
Unfortunately we will be in Madison during the week and the farmer’s market appears to be closed then 
However Capitol Square looks like a great place.
I’ll echo the recommendation for Kopp’s. It’s super approachable and an easy lunch spot that you’ll think of now and then from now on.
I went to college in Milwaukee and, living on the East Side, I walked/biked past Zaffiro’s almost every day. However, being a broke student, I never visited. However, the delicious smells pumping from the place were really good and it now tops my list of places to try when I return to Milwaukee.
This one is a little more obscure thought the place is well know among fans: Points East for chicken wings. I only went there a time or two but they really delivered. 15-20 years ago, they had really limited cooking capacity and it looks like they’ve modernized so do some research if you try to make a visit.
Take a lap around the square (and go inside the Capitol, the dome is impressive. If you’ve got time, you can walk/elevator/climb to an outdoor observation level).
Then head down State Street (lots of quirky-cute shops… The Soap Opera, Little Luxuries, Madison Modern Market, and (my favorite) Anthology. Also lots of bars and coffee joints.
At the end of State Street, you’ll see the Memorial Union, home to the most picturesque place to have a brat ‘n’ a beer… the Union Terrace. Google Image Search that suckah, it’s wonderful.
I do not recommend House on the Rock, but nobody listens to me on that.
Taliesin is definitely worth a visit. Also, if you’re going to be in that area, I recommend seeing a play—any play—at American Players Theatre.
Thanks everyone for the suggestions - the trip was great and we really enjoyed Wisconsin. We loved kayaking the river through downtown Milwaukee, and enjoyed a beautiful sunset at Harrington Beach State Park. We also kayaked part of the Sugar River (which was okay but not great), but we had a great time exploring the towns of Paoli and New Glarus. Unfortunately the brewery was closed to visitors, but the town was super cute. The area around the capitol in Madison was also really nice and I’m pretty sure we walked every street within a mile radius 
We enjoyed drinks and an appetizer at Mader’s, and the pizza recommendation for Zaffiro’s was spot-on. I was also really impressed by the Mexican food (particularly given how far north Wisconsin is) - we had birria tacos from Tapatios Cocina Mexicana in Madison (or I guess technically Fitchburg) that were AMAZING.
And for the most important part - the cheese! We got fresh cheese curds at Clock Shadow Creamery in Milwaukee, and they were delightful! Also stopped by the Wisconsin Cheese Mart and picked up a few things, but their aged cheese selection was a little limited (I think they just needed to restock). In Madison I was able to sample and buy some 10 and 15 year old cheddar made by Hook’s, and I think I’m in love. Once my stash runs out, I will be trying to track down some aged cheddar locally.
Thank you again for the recommendations! You guys definitely steered us in the right direction on multiple things. I wish we had had more time, but if I make it up there again I definitely have some things I still want to see or do. Hopefully I can go a little further north then as well.
I’m not sure about Madison, but Milwaukee has a pretty sizeable Mexican population (about 11%). Whether you want “fake” Mexican or Authentic Mexican or “white people/gringo” Mexican you can find plenty of Mexican restaurants here that will serve what you’re looking for.
But did they squeak? (They should have if they were from Clock Shadow).
ETA, you were right near the Allen Bradley Clock, the largest four faced clock in the world. It’s where this old video came from and why that creamery is called “Clock Shadow”, as in, it’s in the shadow of the clock.
