Crawfordsville looks like a good choice. I have a dog crate in my plane. Usually I can put a dog or two in the crate in the baggage area and then put a couple in the back seats using a leash through the seat belts. That assumes that everybody gets along.
Since I have a small plane, an Archer II; not a lot of room for big crates.
What time do you expect to arrive at Crawfordsville?
N9782C - C56 - SEL - IFR