Advice Needed: 3 month loop

Hi there,

I'm new to the forum, so thanks for helping me out! My girlfriend and I are planning an upcoming road trip that will take us from California out to New York and back again in about 3 months (this August - November). Basically, we'd like advice on routes, destinations, and any other advice you might have for us given the main structure of our trip. . .

We've got some main destinations picked out along the way, and will be starting our trip by looping through the South and then up the Atlantic seaboard (we've only got three weeks for this leg), and then we'll be continuing on up through New York and on to Montreal, then west through Canada, down through Buffalo, and back west somehow towards Vancover, then down south again along the west coast to northern California (we've got 1.5+ months for this half of the loop). So that's the very basic breakdown - I'll post our more detailed (though still incomplete) itinerary below in case that helps.

If you have any ideas or advice for us, please share. We'd love to hear! We're trying to do this all pretty cheap, somewhat off the beaten path, and see as many unique/scenic/worthwhile places as possible. We're game for pretty much whatever, so we're all ears. Thanks again for your help, and here's our preliminary itinerary so far (please help us fill in the gaps and find some beautiful places/routes between these destinations!):

EASTBOUND LEG
San Francisco
Los Angeles
Las Vegas
Santa Fe
(Any ideas here? I know nothing about the Southwest!)
Arlington/Dallas
Austin (Maybe)
Houston (Maybe, less direct but maybe prettier?)
Baton Rouge (maybe)
New Orleans
(No idea how to get from here to the next destination or what the next destination should be - HELP, what should we do/see in the Southeast?!)
Birmingham, AL (Maybe, might be too far north? Better to start heading up here, do you think, or hug the south a bit further through Florida?))
Raleigh/Chapel Hill
Washington DC/Baltimore
Philadelphia
New York
(Wheew, what do you think?)

Eastbound Return Leg
(Any ideas here?)
Wilton, CT (Relatives here)
Cape Cod
Boston
Up through Vermont (Relatives in Moretown)(Any other suggestions?)
Montreal
Ottawa
Toronto
Buffalo/Niagara Falls
Athens, OH (My sister goes to school here)
(Any suggestions for this long stretch?
Chicago
(Here's where things start to get pretty uncertain for us - we don't know much about the northern midwest, so any suggestions would be great)
Madison, WI (we've got a friend here)
Option 1: Head north up toward the border Canada, then west toward Glacier national park - no idea what's up this way!)
Option 2: Head west along a more southerly route, toward through South Dakota (Mt. Rushmore, any other ideas?), on and up through Yellowstone, and north toward Glacier
Any ideas on these two options?
Vancouver Either north through Canada, or more south through the US - thoughts? We'd like to go to the North Cascades somewhere along here)
(Ideas for this long stretch)
Seattle/Olympic National Park
Mt. Rainier National Park
Portland
Eugene
Crater Lake
Mt. Shasta
Back home again!!!

Hello and welcome to the RTA forums !

What a wonderful trip, oh I wish I could find 3 months to take a trip !

With a main list of places decided upon and split into segments, you might be better off at this stage to keep looking at the map and searching the RTA site for ideas and inspiration in each segment, and see what it is that appeals to you, as there would be literally millions of suggestions and far too many to list. As well as the City's you have listed there are many National parks, state parks and other areas of natural outstanding beauty.

This one thread has thousands of ideas to get you started.

I am not a weather expert across the country, but you should be aware that you are starting in the South when extremely hot and ending in the North where places like Crater lake are getting into winter mode by November.

Keep going and as and when new questions arise just ask, enjoy the planning !