3 week roadtrip from CT to Portland, OR

Hi! I've been reading this site for awhile, and finally decided that maybe it wouldn't be a bad idea to post myself asking for advice! I'm moving cross country and since I have the time, decided to make it into a roadtrip as well!

I'm leaving West Hartford CT at the end of this week and my cousin and I (early 30s, late 20s yr old females) are driving to Chicago. We planned 5 days for this.

After that I'll continue on my own from Chicago to Portland OR, stopping in South Dakota at a friend's house along the way, but everything else is up to me. I planned 2 weeks for this leg.

Basically, any advice would be appreciated, but mostly:

1. thoughts on cheap, but safe places to stay
(I would love to camp, but I've only done it 2x before and don't have a tent, and I'm a little leary of doing it alone on my 2nd leg anyway)

2. thoughts on parking my car safety, especially if the car has lots of stuff in it
(I'm moving and though I'm packing light, it's still making the car fairly full)

3. thoughts on laptop safety
keep it in the car trunk which might be stolen and get hot? keep it in the hotel/motel/hostel room/safe/locker?

4. cool things to see along this northern US route (and places that sound good but should be avoided)
I also love great restaurants and am willing to splurge a few times for something fancy if there's a special place along the way. Some parks are pretty much a given with my route (Mt Rushmore, Yellowstone), but I was also hoping to see a few art museums, and perhaps just some weird/unusual things!

Thanks so much!!

Cheap and Safe Places to stay: Hostels come to mind first, but since I've never done them personally, I have no idea where they are along your route. Hopefully someone else will chime in.
For motels, there are a few thoughts: First, stop at the State Tourism Bureau which are often located along major highways just as you enter a new state. There, you can pick up freebie booklets full of motel (and sometimes restaurant) coupons. Traveling in June will get you better deals than in July, probably. Otherwise, stick to mom-and-pop motels, or Motel 6.

Parking safety: When you're packing your car, ensure that electronics are packed either in your suitcase (that you take inside with you) or at least in the trunk. Don't leave an iPod, GPS, iPad, laptop, etc within plain sight - that's an invitation to a break in. Park under a sodium light if you can. Yeah, you may get some bird droppings on your car that way, but your car will be in full view. When going into a restaurant or store, try to park where you can see your vehicle.

Our laptop has traveled safely during the daytime in our trunk. We stop at restaurants, fuel stations, etc., with no problems. During the night, we always take it into the hotel with us. (Heck, most motels have Wi-Fi these days. Motel 6 will charge $3 extra for it, as do some other chains.) I'm not sure about hostels, hopefully someone else will chime in with it.

Do you have a AAA membership? We've found that to be invaluable. Not only the peace of mind if we get into a vehicular issue requiring a tow, but also the discounts (motels and restaurants) and the tour books.


Donna

If you are going to see Mount Rushmore you should check out the Badlands, which should be right on the way in SD on I90 and Devil's Tower, WY, which is about 30 minutes off the highway. For unusual there is a minuteman nuclear missile silo (decommissioned of course) that you can visit along I-90 in SD too. I happened on this and there was a very friendly park ranger there to show me around.

If you are all the way out at Yellowstone, it's about a day's drive to Glacier National Park, however if you do this you should check if "Going to the Sun Road" is open, it may still be blocked by snow even in early June. If it's closed I'd probably pass on this. Another possibility would be to head south to the Grand Teton National Park, this would be a lot closer to Yellowstone.

Motel 6 is fantastic for a trip like this, but you can find lots of great deals on cheap hotels. The $3 for wifi is annoying, but they are still usually cheaper. Definitely don't leave anything like a gps or laptop sitting out in plain sight when you leave your car.

Also you can probably make it to Chicago in 2 days, and with 2 drivers maybe even 1 day (that might be pushing it though).

Motel 6 is (on paper) less expensive than other chains, but they charge extra for things that are also included the basic lodging fees of other chains. Personally, I think the the best deal out there is at Holiday Inn Express motels. The beds are comfortable, Wi-Fi works, breakfast is included, shower heads are great, and because most utility firms working in area stay at Holiday Inn Express locations -- the security in the parking lots is often excellent.

Wherever I am -- my laptop is there 90% of the time. There are exceptions and in those situations, I put the clothes from my suitcase in the wardrobe and put my laptop case in my suitcase and lock it.

Mark

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Originally Posted by DonnaR57

Cheap and Safe Places to stay: Hostels come to mind first, but since I've never done them personally, I have no idea where they are along your route. Hopefully someone else will chime in.

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Probably the most comprehensive site for hostels world wide is www.hostelz.com

I have stayed at many hostels in many countries, and like all accommodation, some are great, and others you wish you had never seen the place. However, the best thing is to ask on arrival if you may see a dorm or room. If you are told that it is not possible, ask to see a bathroom and the kitchen. These will give you a very good idea of the standard of the rest of the hostel. Try to avoid places where sleeping bags are allowed. These are a main cause of spreading bugs and insects. The other thing to look for is lockers. Check that each bed - even in private rooms - has a locker. And make sure it is a locker for which you provide your own padlock. The ones where you put money in, and take the key, are able to be accessed by the management of the establishment.

Along the route you will be travelling, I have not stayed in many hostels, and even when I did, it was a long time ago. Which brings to mind, when reading hostel reviews, concentrate on the ones written in the last couple of years. A lot can change in five years. And whereas I may have found a hostel in pristine condition then, it may now be a dump. (That goes for most accommodation.)

And make sure you leave a review to help those who come after you.

Hope that helps.

Lifey

Thanks for the great advice (especially about the possibility of the Glacier road still being closed).

We were hoping to have some fun exploring along the way to Chicago (made a Barnes Foundation reservation etc), but we don't seem to be able to find anything "must see" once we hit west Penn, northern Ohio and Indiana. We were wondering if there are some roadside attractions/sights/anything people like to do in these areas that we're missing. We were thinking of going into Michigan, but it wasn't really in the initial plan.

Sorry about my lateness in replying and thank you so much to everyone for the great advice! I do have a AAA membership and I'm comfortable with hostels (though not sure about parking my car near some of the areas that they're in...) I'm also definitely going to check out the Badlands (and probably the missile silo, since my parents missed it when they were out there and regret it)

Some more detailed points I found especially helpful:

Glacier was on my "to do" list, but I never thought that road might still be closed this late in the year! Thanks for the heads up--I'll definitely check!

Parking under a light at night sounds like a good idea.

The sleeping bags thing at hostels spreading bugs--erk! I know one that I've stayed at recently didn't allow us to bring in pillows/sleeping bags, and it makes sense now. The padlock and pre-viewing and recent reviews only are also good points.

The laptop in the locked "empty" suitcase is a great idea!!

I think I might be going with the Holiday Inn Express (I've stayed at them before) and sometimes Motel 6 route. Mostly because I have a car with more than I'd usually bring on a regular trip, so security is pretty important to me. This might be more expensive than hostels, but I think the peace of mind will be worth it.

The slightly-loaded car is more trouble than I'd at 1st thought. We were going to stay with a friend in Chicago, but she only has metered street parking, and she doesn't trust her street's safety. Looks like it's a motel there after all, instead of the free room we'd thought we'd be getting! Oh well.

Check with individual hostels along the way. I have stayed at many which had secure parking, especially in worrysome districts. When I was relocating cars, I was obliged to have the car securely parked overnight, and found that many hostels had that... often free.

Lifey

No idea about the hostel secure parking! Thanks for the heads up!