So here's the story. My boyfriend and I try and go somewhere every fall. He's a chef at a country club and I'm a teacher in a year round school so fall and spring are the easy times for us to get time off. Usually we either go to North Carolina to a family beach house, Chicago or Massachusetts to visit family (we live in Maryland), but this year we are entertaining those options as well as going somewhere new and non-family related; somewhere just for us. We entertained some classic options like Vegas, a cruise, etc and then my boyfriend threw out the idea of going to Oregon. I thought why not and then he threw out the suggestion of driving there. Obviously this would be a cross-country trip (from MD to OR) and I started thinking more about it. I have done a lot of looking around on-line over the last few days and found the book "Road Trip USA" by Jamie Jensen. It has an Oregon Trail trip in it that runs from Massachusetts to Oregon. Now I have a few questions. And please keep in mind that this is the very very very early stages of planning and I have a lot of options and decisions still to make if this is what we are going to do.
1) What is the latest/earliest it would be reasonably reliable weatherwise to travel the route in the year? We normally go in October/November or February/March. Not sure when the weather gets bad around the northern Rockies.
2) I'm thinking a realistic 2 weeks for this round trip. Does this seem accurate? I mapquested the quickest route to Portland and it said 41hrs one way. I figure we would spend at least a day or two in Chicago visiting family.
3) We have 2 medium-sized dogs that I would like to travel with (I think!). We have a dog sitter (roommate) available if we decide to leave them at home, but they are part of the family and I can't imaging being away from them for 2 whole weeks. Any tips/cautions/ideas as far as this is concerned?
4) With the previous comment in mind, I have a Chevy Cobalt which we could drive, however I was considering the idea of renting a small SUV or minivan, especially if we are bringing the dogs. I've looked at some rental places and just wasn't sure how the milage might work. I'm concerned it may not be financially viable to rent a car if I have to pay for 5000 miles. Ideas?
5) The "Road Trip USA" book has routes on 2-lane highways. Is it worth taking the scenic route and taking longer, or going for the interstate route and making things a bit quicker?
I appreciate any feedback/comments as I try and get this potential trip together.