Where to go?

[benton]

Asheville is worth checking out for sure. I'm a big fan of North Carolina in general as well.

 

[Timothy Englert]

Go south!!!...unless you like cold, misery, and death on some slippery road...Bike touring is demanding enough without winter.....and get some bike pants and a good compact air mattress ...they saved my ass literally .....I toured the Adirondacks this summer; Route 3 Watertown to Lake Tupperdown to Utica try it next summer...you can for $10 put your bike in a box and take the bus south, or certain Amtrak Trains now take bikes as is.When I was done I put me and my bike on Amtrak and went back to Buffalo....

 

[Older Than Dirt]

Bolt Bus takes bikes unboxed.

Megabus depends on the driver and how crowded, but mostly you will need a box.

Greyhound always needs a box.

 

[Muffin Mouth]

Wherever you start from and whichever direction you go I recommend inquiring at local bike shops about maps for cyclists. Sometimes those organized rides that yuppies pay to participate in have really nice routes that avoid roads with nasty traffic and are often dotted with pleasant campgrounds. Sometimes they even spray paint stencils letting you know where to turn. The STP (no pun intended) route from Seattle to Portland is lovely, or at least it was ten years ago. I have never done it, but the pacific crest trail (down the west coast) might be rad.

 

[MFB]

Kudos, youre much braver than I am if you stay north, not a lot of daylight and some cold nights youll suffer through, but I bet itd be pertty.

I would look into the Florida Trail. Its flat and you could cruise. Ive never done iy but my parents have. Lots of wetlands and cool birds, but mosy importantly for me, warmth.

If you have the time check into the Southern Tier, stay warm and see a lot of the country, plus ya get to dip your toes in the pacific when your done peddlin'!

 

[Django]

Hey I guess that by now you should be really locked on your destination. If not, you get plenty of advices so I ain't gonna add my idea.

About winter biking; well, it's sucks. But it's also doable.
I'll spare the gear nececseties (I misspelled that) cause you got plenty of info and will emphasize the mental aspect. The sun rarely comes (I once counted 14 days in northern Ontario. 14 with no sun) and that has a mental challenge of urself. It's always gray.
There's always this weird rain-ish that is kinda like hail sprinkles and so you will always be wet and therefore, cold (and sleep uncomfortably ofcourse).
The scenery is not as amazing, since it's always cloudy.
THE MORNINGS. Time to wake up. You can have the best gear in the world, but everyday (or most days, as there aren't many active hosts along the way) you will have to leave your warm -9999 sleeping bag and 5 season tent. That to itself is extremely hard and dissing. You look at the watch, it's 09:30 am and still dark. But you gotta start the day, even if it's fuckin 15F outside. Sun sets at 4:30~ pm.

Some photos from Montreal-Vancouver (biking with some hitchhiking pickup trucks) and from Vancouver-Whitehorse in January, hitchhiking.

The picture in the dark if the van was taken at 9:30 am.
In one of the pictures with my bike in a steep climb, my water bottle froze the next morning. Could t drink.

Thoughts about that emergency blanket: it's horrible. All your sweat will gather. Impossible to sleep well with it.

Also I've added a long stretch of borring flat road with no sun and living soul for a 100 miles (and that's not a small info stand).
It can really get in your mind.

Not trying to spook you, just to give a better understanding of what it feels like. The gear sure, have good gear, but these are the real challenges you'll face, and many more.