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Louisville and/or Nashville would be my choice. You can get to Louisville from St. Louis in about 4 hours via I-64 and then to Nashville from Louisville is only about 2.5 hours. I am also into taking road trips and sometimes enjoy just driving around new cities. In Louisville, I would check out at least one Bourbon distillery which give great tours and are affordable (Jim Beam is just off I-65 in Clermont, KY). Check out Waterfront Park and the Big 4 Bridge and if you like Baseball, the Louisville Slugger Museum and Factory.
I know much of what Nashville offers has already been mentioned. Broadway and all it's bars and honky tonks sure are fun, but I also enjoyed touring the Ryman and if there is a show (usually during the winter) it is an awesome place to see. Andrew Jackson's Hermitage is near Nashville and is a cool place to check out.
I didn't realise that Tulsa and Des Moines where only 5.5 hrs away.
Serious question, What's interesting in Tulsa and Des Moines?
hahaha well my impression is they could be nice places to live. Des Moines has had a lot of positive press and seems like it is desirable to the urban millennial crowd. I've been following it since 2009 when I was getting ready to leave Chicago and wanted to check out DM (but never did)
Tulsa hasn't been on my radar at all until recently I did some research on RE there. Some people on CD say Tulsa is more urban and artsy than OKC, which are both positive points in my book. Anyway, just places I'd want to check out but certainly could turn out to be duds.
Also, Mammoth Cave could be combined with Louisville, or Indiana Dunes with Chicago, and you could still be within that time frame.
As for the cities listed, Chicago almost certainly offers the most to see and do, but that doesn't make it the end all be all (all of them posted are worth a visit). Cincinnati especially is quite historic, and feels almost European in parts of the Over the Rhine and Mount Adams sections.
Milwaukee is another major city that fits within the borders of your time constraints (albeit not by much). It doesn't have as much going on as Chicago, but is more chilled out yet still offers a lot. Madison is within that range also, as is some of the Driftless Region, including Wisconsin Dells (Waterpark Capital of the World), immediately to it's north and west. Small Big 10 and SEC football towns may interest as well, if you are moderately into sports at all (even just for the atmosphere).
Basically, where you are located, you have plenty of pretty nice options.
Agreed, if the OP isn't limiting themselves to just major cities. I posted a route which goes through Branson, Eureka Springs (which appeals more to me than Branson, but I included Branson because I get why people would like it), and arguably (likely) the most scenic stretch of all the Ozarks (Buffalo National River area). One could do all 3 of those in one loop that would be less than 5.5 hours each way.
But, one wouldn't even have to go that far to get to the Ozarks. Of course, the Mississippi River Bluffs even around town are quite impressive, but about 90 minutes from Downtown STL puts you at stuff like this: https://bloximages.newyork1.vip.town...=crop%2Cresize
I think someone else may have echoed this too, but Springfield, IL would work as a day trip, too.
I live in Saint Louis and love to take road trips. 5 to 5.5 hrs is max. Here is the listing of cities on our list. What is your favorite and why. There is no right or wrong answers. Just looking for opinions.
Memphis
Kansas City
Chicago
Indianapolis
Cincinnati
Louisville
Nashville
What is the purpose of the road trip? Vacation, museums, sightseeing?
Branson, Missouri
Nashville, Tennessee
Galena, Illinois
Fairfield Bay, Arkansas
Villa Rica, Georgia
Crossville, Tennessee
Memphis--avoid like the plague
Kansas City--O. K.
Chicago--an average of two people a day get murdered there.
Indianapolis--all right
Cincinnati--??
Louisville--wonderful town
Nashville--You can't beat it.
Our experience is that National Parks work better than cities. Tennessee has great state parks too and both Arkansas and Tennessee have beautiful scenery as you are going there.
I would add Milwaukee, WI and Madison, WI. Both are 5.5 hours away.
Summerfest (Milwaukee, Wisconsin) - The worlds largest music festival. Located on a dedicated lakefront site with all the appropriate infrastructure and diversions built into it. (No temporary stages. No port-a-potties on a city street.) 11 Days on 11 Stages from late June to early July. 800,000+ in attendance.
Miller Park (Milwaukee, Wisconsin) - Fox Sports: Major leagues biggest tailgating scene. #1 in per capita attendance in the majors. Winner of ESPNs battle of the ballparks. North America's only fan-shaped retractable roof baseball park and the only stadium in the Midwest that provides a comfortable environment even if it's cold or rainy. People from all over like Miller Park. It fills a niche that no other park fills for a thousand miles.
Especially if you're close. If you live in the Midwest there's really no reason to even fly up there and drivings cheaper than flying. In many trips, travel costs can be half or more of all expenses.
Byt why drive to Chicago? No way. Unless you're going to stay in the burbs, require a car to get around and want free parking at the motel driving is a bad option for a weekend get-a-way? A quick flight trip from STL to Chicago is cheap and takes 30 minutes. Catch the Orange line from Midway and you're on State St in the loop within an hour of landing.
Road trip (drive) to Chicago and you deal with:
Tolls
Parking
Traffic
Gas
Time
With flying you have to deal with airlines (TSA, baggage fees, less flexibility on time, airport transportation etc.) and if you are going with multiple people, everyone has to have their own ticket which is more expensive than pitching in for gas. Road trips are also just more fun. That's my bias though, because I love driving and only fly if I don't have the time or am going by myself.
Teach me, I went to Chicago last summer and paid $180 for 2 days of parking alone.
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