Milwaukee is a great place to visit. It has more things to do than any other city in our great state, and you’ll never find yourself bored there. If you know how to plan a great trip, you can visit for cheap too. But getting there can be half the fun too, if you know how to do it right. Since the majority of our state lives in the two metro areas of Madison and Milwaukee, let’s talk about the best route to travel between the two.
The obvious route connecting these two population centers is I-94. Now if you’re in a time crunch, or say traveling with a large group of people, or just don’t go back and forth between these areas very often, then perhaps this major highway is for you. I hate it though. Depending on which direction you’re heading, going from 4 lanes to 2 right around Waukesha is a nightmare. And even if you’re going east and are gaining those two extra lanes, the speed limit slows down significantly, and suddenly everyone around you forgets how to drive. I always feel like its a miracle if I avoid an accident in this area with how poor the other drivers are. So if possible, I go out of my way to make sure I don’t have to deal with it.
If you recall from other posts in this series, we do have a few rules to follow when choosing these alternate routes. 1) Back roads should be in consideration. In all cases county highways are still backroads. 2) County highways should take priority over the interstate, and 3) You should still make it a point of emphasis to travel in the same direction, meaning, you shouldn’t be going TOO far out of your way. Anything more than 30-40 minutes is probably counterintuitive. So now that we have our rules refreshed for us, let’s get into the best alternate route between these two metropolises.
In my opinion, there’s really only two realistic alternate routes for these cities. You could try a combination of Hwy’s 19 and 16, directly to the north of I94, or you could go the way of Hwy 18, directly to the south of I94. I have one preferred route I’ll give below, but honestly I think the bigger factor might be your exact start and end point. If your starting point is further north of Madison or Milwaukee, I think the 19/16 combo is the way to go. If you’re starting and/or ending a little south in either of those two cities, then Hwy 18 is your jam. Both routes will be WAY less crowded, feature way less bad drivers, and offer more to see and do in terms of stops and breaks along the way.
I’d like to cover a few of the best things do along each of those routes. Starting with Hwy 19 departing from the Madison area, your first two towns will be Marshall and Waterloo, respectively. Both have a few good features, including some cool dive bars, Marshall with its top notch Mexican restaurant, and Waterloo with its antique stores. Before arriving in Hubbleton, you’ll also have passed by several really good brief stops to view some nature. Hubbleton is the next town, home of Hubbleton Brewery, followed by Watertown next, which is a very decent sized city with plenty to do and see as well. Watertown is also where you’ll transition from Highway 19 to 16 before heading closer to Milwaukee. At this point you’re basically in the suburbs of Milwaukee. A few small towns like Ixonia and Nashotah, among others, and bigger cities like Oconomowoc and Hartland are all that stand in the way of you and our states biggest city.
My preferred route however, which isn’t quite as fast as the northern route, but just as much to see and do, is the southern route along highway 18. Departing from the Madison area, your first three towns are Cottage Grove, Cambridge, and Jefferson. Two wineries and a distillery are featured among these cities, and they are some of the most charming towns our state has to offer. Jefferson in particular is a favorite of mine for a variety of reasons. From there its really a quick drive over to Wales, the next major city before getting to the MKE suburbs. Just outside of Wales lies a very cool antique store in an old barn with some great finds. Once past Wales, you’re essentially in Waukesha, which for all intents and purposes means you’ve arrived.
Both routes are under 2 hours which is a plus for any good route. At worst, you’re arriving 20-30 minutes later than you intended. At best, you’re arriving at a roughly similar time depending on your exact starting and stopping point, and if traffic is bad, you might even end up saving time, and perhaps avoid an accident or two. You’ll have better views, and more opportunities for a spontaneous pit stop, if that’s your thing (it needs to be your thing if it isn’t). Again, of the two routes, my preference is the southern one, Hwy. 18. In my opinion it’s a little more time, but better views, and the western segment has more to do in terms of spontaneity. Jefferson is definitely one of the most underrated and charming towns in southern Wisconsin, which isn’t accessible if you take the northern route. Less traffic than 19/16 too, which is always a good thing.
TL;DR
– Of the three routes in between Madison and Milwaukee, the northern route consists of Hwy. 19 and 16, the southern uses Hwy. 18
– Northern route (hwy. 19) is faster, with bigger cities/towns, leading to more options to stop
– Southern route (hwy. 18) will take longer, but has better views and less traffic
– Attractions: great antique stores (one near Wales, one near Waterloo), brewery in Hubbleton and a Winery/Distillery in Jefferson, Winery in Cambridge, and plenty of other random things for spontaneous stops you might need to take
Life is Too Short to Take the Fast Way 