Road Trip Guide: Milwaukee to Nashville


Over Labor Day weekend we took a road trip to Nashville, TN and found some real gems along the way. And by gems I mean road side attractions, gifts shops, diners, neon signs, breweries, and general beautiful Americana. I don’t want to write about our vacation as much as the potential that a vacation like this holds. So here’s a guide in case you ever decide to make the trip.


On the way down we stopped in Indianapolis to refuel…with beer. We found a brewery with a tasting room that was still open called Flat 12 Bierwerks. Apparently Indiana’s laws don’t allow kids past the lobby – the bouncer seemed confused when we walked up with a two year old in our arms but then she saw our ID’s and WI’s reputation preceded us – she understood. Anyway, the beer was just as good in the lobby and they sold “bullets” to go which was basically a plastic water bottle filled with beer. (Why don’t we have those here?)


The gift shop at the Kentucky Museum. We didn’t actually visit the museum. We just heard there were a lot of white squirrels nearby and the gift shop came through with white squirrel souvenirs – we bought a small white squirrel candle. I also liked the ceramic KFC chicken bucket but didn’t even ask Tara if I could buy one of those.


We waited an hour and a half for breakfast at the Loveless Cafe and generally that would have been unacceptable to me; but it was worth every minute for what might have been the best breakfast I’ve ever had. Yes that is a pile of pit smoked barbecue pork in between my eggs and grits. The biscuits and jelly were also amazing. On top of all that it had a great sign and a respectable gift shop. This must stop is on the outskirts of Nashville, TN.


A Pink Elephant drinking a martini. Looking into the eye of the beast I shed a tear for his glory days of yore. (Across from Sad Sam’s off I-65 in TN)


Nervous Charlies had a Gorilla, some good souvenirs, and some questionable ones. (Off I-65 in TN)


A Giant Indian at Sad Sam’s off I-65 in TN.


They just hang their ham out in the open down there which seemed weird but it smelled good…really.




A re-creation of a giant prehistoric crocodile was just one of the reasons for stopping at Big Mike’s Rock Shop in Cave City, KY. The great selection of rocks, lots of souvenirs, and last but definitely not least a “Mystery House” where we defied physics made this place a highlight of the trip.


Sharptooth! Or just your greeter to Dinosaur World in Cave City, KY. Unfortunately we didn’t get to visit due to rain.


Wigwam Village #2 in Cave City, KY. These cement wigwams are a motel, if that’s not as awesome to you as it is to me then my words will not do them justice. This is one of three remaining Wigwam Villages in the US (probably the world) and we had every intention of spending the night in one until a storm flooded our reserved unit and several others. Next time. (Read more about them here:

And as a side note, Cave City in general is definitely worth the stop. Obviously, they have a lot of caves, which are awesome in its own right, but they also have a bunch of touristy stuff that time has just passed by. It’s wonderful and a little sad, definitely worth a stop.


Lynn’s Paradise Cafe in Louisville, KY had a cool sign, brightly colored fiberglass animals outside, and the above pictured dish. They called it a sandwich (I think there was bread in there somewhere) – I called it tasty. For your own reference though, the service was poor and it smelled a little weird in there.


A well placed stoplight downtown Louisville.

Conclusions:  These were just a few of the off-the-beaten path places we found. The more mainstream stops included a couple good breweries in Nashville (Jackalope was our favorite), lots of Bourbon in Kentucky (Heaven Hill had a nice tour and tasting), Churchill Downs and the Kentucky Derby Museum (I think we saw Li’l Sebastian) , the Louisville Slugger Factory and Museum (don’t let your two year old touch Mickey Mantle’s bat without gloves, also don’t grab it away from him without gloves), and plenty more that you’ll have no trouble finding.

My advice for your next vacation? Glad you asked. Drive somewhere, get off the freeway, stop at places that look like dumps (and then stop somewhere nice cause some really are dumps), buy souvenirs that are covered in dust, eat the local food, drink the local beer, and just go see America.