Boston to Big Horn, WY solo in Sept.

I'm taking my first ever solo road trip the first week of September. I have about a week to get from Boston to Big Horn, Wyoming, which I think should leave me a little room for flexibility in my planning.

I'd like your suggestions of interesting places, funky towns, state fairs, cool art, or amazing natural wonders. Since I'm driving by myself, I'd like to mix in some short days with long days to break things up a bit. My first few days are pretty set-- probably Boston to Rochester, NY, and Rochester to Ann Arbor, MI as I have family in both of those cities. I'll probably pass through Ontario on the way to Ann Arbor, for more friends. And probably a night in Chicago. Aaaannnnd.... that's all I've got so far. I'm an East Coast gal and after Chicago it's all a big mystery to me.

I'm an artist and will go out of my way for cool art museums or nifty folk art, underground art, or even just excellent graffiti art. I also love carnivals. I have lived my whole life in big cities, so I'm psyched for some small towns and historic old architecture. (Galena, IL looks interesting from another road trip site I was reading. ) I'll be carrying my hybrid Trek on the back of the car, in hopes of stopping for some fun bicycling along the way. A 20 or 30 mile loop on a beautiful bike-path would be a great half-day break from driving. [My last big road trip was when my husband I road our bicycles from Boston to Montreal and back last summer!] I won't be able to pack camping gear this trip, but I'd like to hike in Badlands in SD and would love a good place to stay near there.

I need to arrive in Big Horn, WY by lunch so my last night of my trip should be near there. Again points if it's nifty.

So? For a first time Road Tripper... what should I be sure not to miss this September?
(Also, I'll be driving back again in October, if there's something I can't catch on the way out.)

Thanks so much! I look forward to reading any trip-planning ideas you have to share!

-Barn Stormin' Jenny

Hi Jenny, and Welcome to the Great American RoadTrip Forum.

You are heading to one of my favourite regions, and one I try to see on each of my trips. From Chicago, your most direct route will be along I-90. There are many small towns along and near this route, and from my experience, I find that almost all small towns have a gallery of works from local artists. I always find these of great interest. The welcome and visitor centres in each area would have the details.

Other popular attractions along - and very close to - this route are Corn Palace in Mitchell, WallDrug in Wall, Badlands NP, Mt Rushmore, Custer SP, The Center of the Nation at Belle Fourche, and Devil's Tower.

Have a look around the trip planning pages and the forum, and I am sure you will come up with many more places which interest you.

As a solo female traveller myself, I can assure you that so long as you take the normal security measures you do at home, you should not have any problems. It is a great comfort in case of any mishaps, to be a member of a roadside service organisation such as AAA. Cheap insurance you hope you never need. And who knows what interesting folk you might meet along the way.

Have a safe trip.

Lifey

If you have the time, I think you would in fact like Galena. From there, you can take US-20 across Iowa to I-35 or I-29 to get to I-90. If you are at all interested, you would be going right by the Field of Dreams outside of Dyersville if you take US-20.