Portland to Boston -- in 2 weeks?

Hi Jamie,

Myself and my friend have finally booked our flights to drive this great trip. We fly into Portland and out of Boston and have 2 weeks to drive the route... but mapping it out etc, I'm now in a panic that its gonna be all drive and no play!!! We have done several road trips together through the southern states and also Canada, but this is the longest by far.

Do you think 14 days is really enough time to do this trip in?

We are planning driving our first day spent in Portland then up early and leave Portland to Vale, stop over here then Vale to W Yellowstone where we will stop in Yellowstone for 2 days. We then leave for Cody and stop over in Cody as a day to have a shorter drive on and a free afternoon. Then the next day leaving Cody for Keystone and Mount Rushmore with an overnight stay.. then on to Sioux City or Falls.. not sure which is best! Overnight here then on to Chicago with 1 day in Chicago. Leaving here for the long drive onto Buffalo and Niagara with one day stop over there and then onto Boston leaving only the day we fly out as the only day we get in Boston!

Is there a better way to plan this trip with the time we have??...

It would be great to hear your views and any tips on this long trip if you have any. We are planning the days when we have 7/8hrs driving to stop at interesting points along the way but will be only quick photoshops.

Many thanks for any help!

Sarah



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Hi Sarah --

Many thanks for writing in to Road Trip USA -- you didn't say when you are hitting the road!...

But if you haven't yet set off, I think you'll find that 14 days is plenty of time.

(Obviously having a whole month or so to zigzag across the country would be even better, but then again a work-free life of leisure & luxury would be pretty nice, too, wouldn't it? ... )

Portland is among my favorite places, so it should be a good start for your trip. I'd head east thru the Columbia Gorge, stopping to listen to all the lovely waterfalls before heading on to Vale (whose brown flatness will be a sudden sharp contrast to the lush canyons of the Columbia.)

Then across Idaho, up into Yellowstone for 2+ days, I'm jealous. Cody next, then Keystone / Mt Rushmore (and Wall Drug, I hope!).

You said you were pondering Sioux City or Sioux Falls; given that choice I'd opt for Sioux City, but if I were in charge I would probably decide to make this a longer day and go all the way across the Great Plains to really nifty little city of La Crosse Wisconsin. La Crosse is very quaint yet lively, with a nice old downtown plus all the burgers / beer / ice cream etc any road tripper could want.

If I didn't desperately want to see all there is in Chicago, I might be tempted to extend and enjoy the next part of the drive by winding a ways south from La Crosse along the Mississippi River to Galena IL, another very quaint, characterful place with good food (I cover the route in the Great River Road section in Road Trip USA!). Also, for baseball fans, just west of here there's the Field of Dreams, a real road trip icon...

We're maybe a week into your trip by now, and already 2/3rds of the way across the USA. Take a break in Chicago? Then bomb east along I-80, with a couple quick detours to keep you sane (Toledo is fun -- great art, good baseball, and famous hot dogs).

I've done the Chicago-to-Boston run in a very very long 48 hours, with a break at Niagara Falls, so you do have plenty of time. Linger a while in Buffalo (art and architecture!), or maybe shift a couple of days to earlier in your plans -- at the start, for example, the Portland area is very cool, and you might want to head all the way west to Cannon Beach, (and out to Cape Cod at the east end?), just so you can have the full-on, ocean to ocean experience.

What's another 200 miles, if it gives you such nice bookends... :-)

Even if a cross-country trip like this does entail a couple of long days behind the wheel, if you break them up with a few quick middle-of-nowhere junk-shop tours, or a nice long lunchtime walk, they won't feel so exhausting. I don't recommend the all-night drive, though -- in my experience any time you save, you end up giving back because you need to sleep all day to recover.

Good tunes, or a few good audiobooks (Little House on The Prairie, even, for that northern Great Plains stretch!), are great companions, and will definitely help the hours and miles pass more happily.

The whole shebang sounds like a great trip.

Happy Trails,



Jamie Jensen
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Road Trip USA