We Planned a Reds Road Trip. Milwaukee and Chicago Had Other Plans.
So remember when I told you Jamie, Lance, and I were road-tripping to see the Reds?
Yeah. About that.
We ended up in Milwaukee and Chicago, which is either a wrong turn or the best decision we've made all year, depending on how you look at it (I'm going with the second one).
Here's what actually happened.
The Hotel Room That Ruined Me For All Other Hotel Rooms
We stayed at the Hilton Garden Inn Milwaukee Downtown, which was lovely and fine and everything a hotel should be. But it's the second stop, Chicago's Hotel Zachary, that I need you to sit down for.
Our room looked directly out at the Wrigley Field Marquee. Not "if you lean out the window and squint." Directly. Out. At. It. Jamie caught me just standing at the window for a solid five minutes like I'd never seen a light-up sign before. I had not seen one like this before.
The view from our room at Hotel Zachary: Wrigley Field’s marquee, a sea of Cubs fans, and the exact moment I understood why people book this room on purpose.
SafeHouse: Milwaukee's Worst-Kept Secret Speakeasy
If you know, you know. If you don't: there's a password. There's a whole bit. Lance took it far too seriously and I will not be elaborating further because half the fun is not knowing what you're walking into.
What I will say is that it's exactly the kind of slightly-absurd, very-fun stop that makes a trip feel like an adventure instead of an itinerary. Ten out of ten. Bring a sense of humor.
The Bar Shuttle Wristband Incident
The Milwaukee Brat House has a shuttle that runs on a wristband system, and somewhere between brat number two and wristband logistics, this became one of my favorite unplanned parts of the entire trip. I'm not going to explain it well in one paragraph. It deserves its own post. It's getting one.
Murals, Bloody Marys, and a Bronze Fonz
Black Cat Alley is a full outdoor mural walk that I did not expect to love as much as I did — genuinely one of those "okay, Milwaukee, you're cooler than I gave you credit for" moments.
We spent way too long following painted koi fish down an alley like they’d lead us somewhere. They did not. Worth it anyway.
The Milwaukee Public Market gave us a Bloody Mary that came with what I can only describe as a full garnish buffet balanced on top of the glass. There's also a bronze statue of the Fonz on the Riverwalk, which — yes, we took the picture, no, I'm not sorry.
The Game Itself (Both Of Them)
Brewers at American Family Field, then Cubs at Wrigley a few days later — a 23-3 win for the Cubs over the Padres, in front of a crowd that stayed loud for all 27 outs. Two completely different stadium personalities, two completely different energy levels, and somehow both exactly what I needed.
So...
What I can do right now: if you want to see Milwaukee and or Chicago, I can book the exact hotels we stayed in — same Hilton Garden Inn, same Hotel Zachary marquee view if it's available — no group required.
Email me at tracy@harmonyhorizon360.com and I'll get you set up.
If enough of you want to do this together down the road, exactly as we did it? That's where the group trip lives. For now: go see it and tell me how it goes.
Related Posts:
See where it started: Taking Our ND Son to Milwaukee — Here’s How We’re Planning It Differently — Harmony Horizon 360 Travel
See other Baseball City Trips: Cincinnati Reds Game Day Trip: Brunch, Breweries, and a Loss We're Still Processing — Harmony Horizon 360 Travel
Taking Our ND Son to Milwaukee — Here’s How We’re Planning It Differently 💛
We have been taking Lance to Reds road trips for a while now.
And somewhere along the way, something shifted. We stopped planning trips and hoping he’d come along for the ride — and started planning trips that were actually built for him.
Here’s the part I didn’t expect: we ended up loving them more too.
Why Sports and Music Trips Work for Us
We started doing sports and music trips specifically because Lance enjoys them. The structure of a game or a concert gives the whole trip an anchor. There’s a thing we’re going to. There’s a time it starts. There’s a reason we’re in this city.
For a neurodiverse traveler, that kind of built-in structure is genuinely useful. But what surprised me is how much Jamie and I benefit from it too. When the trip has a center of gravity, everything else just falls into place around it.
And the other thing — the thing I wasn’t expecting — is that we’ve started genuinely enjoying the parts of the trip we originally planned for Lance. Not just tolerating them. Actually loving them.
Turns out planning for someone else’s joy has a way of sneaking up on you.
The Hotel: Predictable on Purpose
We booked the Hilton Garden Inn Milwaukee Downtown. Walkable, central, familiar brand.
I know some people chase the most interesting boutique hotel in every city. And I get it — I really do. But for us, the Hilton family of hotels has a consistency that actually matters. Lance knows roughly what to expect when we walk through the door. That’s not a boring choice. That’s a smart one.
Downtown location means once we park, we’re done driving. That alone removes a whole layer of logistical stress.
The Food Strategy: This Is the One People Skip
We scope out two things before every Reds trip: what’s near the stadium, and what’s near where we’re staying.
Near Great American Ball Park, we have our go-to spots — the Cincinnati Lager House, the Yard House. Places we’ve been enough times that we know exactly what we’re getting. But some of our favorite meals happen away from the ballpark entirely, in the neighborhoods near our hotel. In Cincinnati, the streetcar line opens up so many great options it’s almost not fair.
We apply that same approach everywhere we go. Before Milwaukee, I’m already looking at what’s walkable from the Hilton Garden Inn downtown and what we can get to easily from there. Milwaukee actually has its own streetcar — The Hop — so we’re already planning to use it.
Here’s why all of this matters more than it sounds.
Lance needs a schedule. Breakfast at a reasonable hour, dinner at an expected time. When we don’t plan this out, we end up stuffed from a big ballpark lunch at 1pm, and by the time dinner rolls around nobody wants the amazing restaurant we had bookmarked — so we end up with takeout in the hotel room. Which is fine. But it’s not a memory.
Breakfast is actually the easiest part. We always look for hotels with complimentary breakfast — it’s one of the reasons we love Hampton Inns — because it solves the whole morning scheduling problem in one move. Lance gets breakfast at a consistent time, we’re not making decisions before we’ve had coffee, and nobody starts the day stressed.
Dinner we actually plan ahead. We know where we’re going before we get there. Not a rigid reservation-for-everything situation — just a real answer when someone asks “where are we eating tonight” that isn’t “I don’t know, let’s figure it out.”
And then there’s the pizza rule.
Local pizza is always somewhere in the plan. In Cincinnati, that means LaRosa’s delivered to the hotel room — especially if we’re staying two nights and need an easy night-before or post-game option. In every other city, we find whoever does it best there. It’s predictable enough that nobody panics, but you still get to try something new. Lance is in. Jamie is in. I am very in. Finding the local pizza is now just a thing we do on Road trips, and I fully support this tradition.
The Game Day Plan
What time are we arriving? Which gate? Where are we sitting? What’s the food situation inside the park?
I used to kind of wing these things. Now I have answers before we leave the house. Knowing the plan ahead of time means Lance isn’t getting information for the first time while we’re standing in a parking lot. That small shift makes the whole day run differently.
For this one we chose to sit in section 222. The photos from the seats look great and a good view of our team.
We Still Sprinkle In What We Want
Planning for Lance first doesn’t mean Jamie and I don’t get a trip. It means we figure out what works for him — and then build the rest around that foundation.
And in this case, it’s hard to go wrong. This is our first time in Milwaukee. We are excited about everything. The food, the city, the ballpark, whatever we stumble into on the way from the hotel. First-timer energy is genuinely one of my favorite things about road trips — you don’t know enough yet to have expectations, so everything is just a discovery.
That’s a good feeling. I’m not taking it for granted.
What I’d Tell Other Families
You don’t have to overhaul your whole approach to travel. You just have to plan one layer deeper.
Know the food situation before you arrive. Have the hotel figured out. Build in structure where it helps — and breathing room everywhere else.
And if you’re traveling with someone who needs a predictable rhythm to the day, try anchoring the trip around something they genuinely love. You might be surprised how much you end up loving it too.
If you want a tool that helps you track all of this — the logistics, the meal planning, the game-day details — that’s exactly what the Away Game Planner is for.
If you travel with a neurodiverse person and you’ve found something that actually works — drop it in the comments. I’m still figuring this out too. We all are.
Other articles that you may like.
How We’re Choosing Our Next Reds Road Trip