09/03/2013 10:05 am ET Updated Nov 03, 2013

Road Trip Top 10

Driving 1,900 miles from Cape Cod, Massachusetts, to Boulder, Colorado, can be stultifying, especially when you're in a car by yourself with no one for company except 15 fish and two dachshunds. How to make it fun? Keep an eye out for the ludicrous, the sad, and the amazing. Use your Bluetooth to catch up with friends from camp in 1984. Listen to every episode of This American Life ever broadcast. And stop for the night in comfy places, where you can sink down into soft pillows, cuddle with the wiener dogs, and watch Downton Abbey (warning: spoilers).

My road trip top 10? They range from the world's biggest prairie dog (Ok, that was on the dachshunds' top 10 list) to crazy Midwest advertisements.

10. Indiana. The billboards on I-70 make me ponder. Who knew that hell has no exit (a pun, I'm assuming, to remind drivers that three days on I-70 are not hell, no matter what they may think)? And I never really gave much thought to buying an RV before, but after driving past 14 billboards advertising four different dealers, I think I'm changing my mind. I kind of like the idea of getting some black socks to wear with my sandals, too.

9. Illinois. Just over the border, there's the biggest cross I've ever seen. I look around for a mega church, but there's no religious institution at all, anywhere to be seen. Is this Illinois's version of "Hell Has No Exit"?

8. Overland Park, Kansas. It's a surprise that we like anything in Kansas. What's to like? But the barbecue in Kansas City is to die for (Jack Stack burnt ends . . . yum), and so is the Hawthorn Suites, a huge, modern executive hotel with rooms large enough for the dogs to actually have their own space. Great breakfast, too. Not that the dachshunds got any bacon or anything.

7. Dayton, Ohio. Amish people, some in-line for Frosties and burgers at Wendy's. Somehow, I always thought that the Amish baked their own pies and roasted their own hams?

6. Missouri. The billboards go back and forth between anti-abortion ads ("A baby: God's greatest creation") and shout-outs for "Adult Warehouse! Novelties! Movies! Toys!" How these two things go together mystify me. Abortion is sinful, but kinky sex isn't? You should have more sex to make more babies, God's greatest creation? But what about the fancy condoms sold at adult sex shops? Don't those mess with God's being able to create?

5. Ohio. The candle warehouse that advertises, "Awesome bathrooms!" with a photo of an outhouse. Even the wiener dogs are grossed out. We do not stop to check them out.

4. Belleville, Illinois. A frozen custard joint advertises its flavor of the day: wedding cake concrete. On I-70 through Kansas, a billboard advertises "Fossil Pizza." Does anyone want to eat this stuff? Who?

3. Kansas. An I-70 truck stop is the only place I've ever been where there's a line for the men's room and not for the women's room. I luxuriate in the glory of it all.

2. Columbus, Ohio. A stream of about 50 antique Volkswagens heading down I-70. Where are they going? To an antique auto show? To a screening of Cars? Are there any dachshunds in the Kharmann Ghias? Why not?

1. All the way across the country on I-70. The Wyndham Rewards program. On business trips, I'm not really consistent about staying at one brand of hotel vs. another. Boy, am I going to change that tune. With the points in my Wyndham Rewards account, we were able to stay for free for six nights on the road. The nice thing about a big hotel brand is that it has a lot of smaller brands under its umbrella; from the incredibly comfortable Ramada in Greensburg, PA (think Jacuzzi tub right in the room and a homemade breakfast with pecan rolls) to the surprisingly quiet Wyndham at the Indianapolis airport, we were able to find free crash pads at every stop - and they accepted dogs, to boot.