*Repost from Travel Ideas*

My boyfriend and I fantasize about going on a road trip from Oregon to New York, but we really have no idea where to start! We also want to go down to Kentucky and up to Michigan to visit my family! I imagine this would be at least two weeks, maybe even three!
The idea is to go across the country, but we have no idea where to stop!
We are huge nerds, but not so much into the national monument thing.
Do you have any suggestions for states/places to stop?
Where should we start with costs? This will be our first real trip and we just don't even know where to start!

Thank you!

This is whwat Google Maps says:
https://www.google.com/webhp?sourcei...on+to+new+york

More ideas:
https://roadtripusa.com/the-oregon-trail/new-york/

This threads a few years old but has some ideas:
http://www.fodors.com/community/unit...and-oregon.cfm

Do you live in Oregon? I do.
Two years ago I took the California Zephyr east as far as Galesburg IL and rented a car from there for a week.
I found geocaches in 11 new states for me including Michigan.
I also attended a one day event in eastern MO south of St. Louis.
I have driven all the way across the US by car but I now prefer to take a train or two and then rent a car.
Next month I'm driving to Winnemucca NV and getting on the Zephyr to Chicago and then the Lake Shore Limited to Erie PA.
We are renting a car from Erie and going as far east as the coast of Maine and getting geocaches as we go in 6 "new" states for me.
We return the car after Memorial day and take 2 trains back to Winnemucca.
This style of travel works OK for me. The Enterprise office is about 100 yards from the Galesburg station. I earn 50 Amtrak Guest Rewards points for every day of my rental with Enterprise.

If the point of the trip is to take a road trip, then you could do that in 2 or 3 weeks. If you want to visit places along the way you might want to add some time.

Lets say you wanted to visit Yellowstone NP and Louisville, KY one way and Michigan on the other way. The driving time without stops for food, bathroom, etc. would take more than 90 hours. If you do the math that's more than average 10 nine hour days with seats in the car. That gives you 1 day at each of your destinations if you do the two week trip.

Time to do a bit of planning and decide what works for you. Consider the cost of things like gas, overnight lodging, tolls, etc. then decide if it makes sense. When we were younger, we did a road trip from CT to Chicago for a wedding and since we were half way to Yellowstone, decided to add some time and visit that too. It was a fantastic trip and we didn't spend as much time in Yellowstone as I would have liked but did stop at Badlands NP, Mt. Rushmore, and a couple of other places on the way out.

We drove back on the fastest route possible with a couple of 12 + hour days, but still consider it a fantastic trip that we're glad we took. Including 2 nights in Chicago for the wedding , we took 11 days. I must admit that the drive back got a bit tiring.

Now that I'm retired we tend to travel at a slightly more relaxed pace and tend to fly to a destination, rent a car and do a road trip to the places we want to visit. This is often not more expensive than driving to very distant locations.

Hey Tom! I do live in Oregon! Thanks for mapping out your trip! It's awesome to know my trip is absolutely possible. I like the idea of renting a car and taking a train back to save strain on driving.

Emallo, thank you so much for your input! Now I realize we have to decide where we want to stop and when we want to stop before we can put a time limit on our vacation! I realize it will likely be a lot of driving and get exhausting at times so we will do our best to plan our places of interests!

Thanks so much for your input!

Where do you live in Oregon?
Where in Kentucky do your relatives live?
Where in Michigan do relatives live?
How much time do you want with each?
When (what time of year) are you going?
Look up drive times between places and make notes of how many days of just driving you will need.
Look at what is interesting near each relative.
Mammoth Cave in Kentucky, for one thing, is interesting.
The Sand dunes in Michigan are interesting.

My suggestion is spend time sightseeing on the way to Michigan and Kentucky.

Save New York for another trip when you can do things on the East Coast - New York, Boston, Washington DC, etc. Fly there and take train in between.

Is your New York dream New York City or just part of New York?
Our upcoming trip will get us by train to Erie PA and we'll be attending a big geocaching event in Allegany State park in Western New York. From there we see friends and family east of Rochester and then go from there to find caches in 6 NE states including one on the coast of Maine.
Boston, New York, Philadelphia and Washington DC are cities that you don't want to drive or park a rental car in.
The Enterprise office is 100 yards from the train station in Galesburg IL. With my 7 day rental, I drove in 20 states for over 3100 miles. I arrived in Galesburg on the California Zephyr and left a week later on the Southwest Chief and came home to Oregon by way of Los Angeles.

What time of year?