Planning a Road Trip + I Need Your Help!

Every year Cory and I try to take about a week-long roadtrip before we meet up with my parents in the Outer Banks of North Carolina. Three years ago we went through a tour of the south (Knoxville, Nashville, Savannah, Charleston). Two years ago we were getting married and treated our honeymoon to Jamaica as a pretty elaborate roadtrip. Last year, we were pretty tight on funds from buying our house, so we took our time driving down to Myrtle Beach, SC and stayed in Cory's parents condo before meeting up with my parents. This year we haven't had many major purchases (other than a new water heater--ugh!) and have been able to scrounge some money away, so we're hoping to hit the road again!

We've been talking a lot about where to go this year, and it seems like we're definitely heading to the mid-west. Cory's aunt lives in the Ozarks and the nearest full-scale town is Springfield, MO, which is perfect because I'm pretty much dying to visit the Red Velvet Shop. So we know we're headed in that direction, but what we don't know is where we're going to stay along the way! So, we have a few options and I welcome your travel/experience input!

Trip #1:

Route 1 includes is leaving Maryland and heading to Louisville, Kentucky for our first stop. We would definitely stay there at least one night, but probably two, so we have enough time to seek out the local flavor. After our two night stay in Louisville, we'd head to Cory's aunt's house for at least 2 days again, so we can check out Springfield and do some hiking around the mountains. Then we would finally make our way to either Denver or Boulder, CO. We aren't entirely sure which city we want to see more, but I definitely can't wait to get my eyes on those mountains! My only hesitation is that the last leg is the longest and usually we try to get those out of the way first. The other thing to consider is that this route is pretty much a straight shot, which might help with gas and lodging expenses. Hmm..

Trip #2:

This route has the same last two stops, but we would be going north near the Great Lakes and staying in Chicago for two nights instead of Louisville. I'm really intrigued by this version for a few reasons. The first is that I've never been to the windy city,  but have always been eager to go. The second is that I really enjoy having a variation of locations on my roadtrips. To me, as a person who hasn't been to any of these cities, there is a potential of all the cities from Trip #1 to resemble each other or to feel the same in some way. I know, for sure, Chicago could add a little spice. Since we'll be traveling on a tight budget, I am researching various hostels to stay and think we might be able to find more hostels in Chicago than in Louisville. However, this trip does add 100 miles to our trip, which is a lot of money considering how much we'll be paying for gas.

Trip #3:

This route is by far the most affordable of the three as it completely cuts out nearly 800 miles one way! I would love to see Denver or Boulder, but if it's not financially feasible, then I think the smart thing to do would be to add Asheville, NC to our trip as we're heading back into North Carolina at the end, anyway. I have heard so many good things about Asheville and have been very eager to go for over a year. Asheville has a cute hostel that I've had bookmarked for a long time called Sweet Peas Hostel. Have any of you ever been there? The nice thing about this trip is that we could take our time and stop in cities like Knoxville, Nashville, or Raleigh on our way back. We have a lot of friends who live in the Raleigh area, which also draws me towards this trip. I'm always eager to see the people who live by where we're visiting! This trip doesn't involve as much driving and gas money would be able to stretch a little further.

So this is where you come in to help us. Have you been to these cities? Have you traveled this road trip? Do you have any suggestions of "must see/do/eat" places? Which road trip sounds the best?

Thank you in advance!