8bit

I haven't gotten out for more than a 4-day tour all summer and have been going crazy thinking about how I won't get a chance again until my university's winter break. Naturally, crazy ideas start coming to me like visiting my hometown Austin on my bike- here's my plan:

Jan 3: Leave Boston on train
Jan 4: Arrive in Chicago in the morning, start riding south
Jan 11: Arrive in Austin, assuming I can do 8* 150 mile days
Jan 13: Big trail race! I'm sure to be in terrible form for it. But hey, trail races are about falling down, eating oreos, and drinking beer.
.... and then not move until I have to come back. Sound super?

Sure, it's ambitious and I'll probably lose a few fingers to frostbite (my BF guarantees me a blizzard). If I need to bail, there's bus service to a bunch of small places along the way. I'm young and I'm supposed to be doing stupid things, anyway. I'm in decent enough form right now to do at least two 150 mile days back-to-back, I haven't tried for more yet. As for the logistics, I'll be travelling pretty light with bivy/tarp style camping gear but will probably spend some nights in motels. Big issues i'm anticipating: weather, fatigue, short days (probably the most difficult)- help me identify the rest of the problems with my crazy plan!

nm+

Jan 4?
With a bivvy tent?
I really hope you ahve one hell of sleeping bag.
And very warm cycling cloths. Lotta windchill out there, you will have negative degree days, esp if you account for the windchill.
Also, think about ice. You'll need studded tires and a plan to chage them out.
How far have you ridden in the winter? How do you plan to keep water from freezing on days over a few hours?

godspiral

If you left from Atlanta instead of Chicago, you could have much more pleasant weather, and at least not have to contingency plan for extreme cold.

8bit

I haven't lived up north very long, my winter riding has been limited. I've been up to a century on winter days, but I'll have time in November and December to get in some day/weekend rides to test out my clothing. I'm thinking that bringing along a face heat exchanger mask and some massive gloves will be a good strategy. As for water, I'm planning on stopping at convenience stores every so often to fill up bottles and buy twinkies and coffee, so my polar bottles won't have much chance to get frozen solid, maybe just crusty around the top. If I need to carry more water I can fill up a platypus and stuff it into a pannier for insulation.

I agree, that would certainly be warmer, but then I'd have to fly . Taking the train with my bike is a lot cheaper and doesn't have the "Security Theater" risk. The best Amtrak routes from Boston go to Washington, DC and Chicago. I'm also pretty sure that the terrain from Chicago is flatter than coming over the mountains (though somebody who's familiar with Illinois could tell me I'm wrong).

Your questions/tips are excellent and really making me think. Keep them coming!

Mooo

It seems like a plan with very little margin for error. A flat tire in 30 degree rain in the dark could turn into a dangerous situation over just a very few minutes.

January is unpredictable in the upper midwest.
I've often thought that a tour in January would be a real sporting proposition (i.e. something that ought to be done for the sport of it), but there are a couple of considerations.

The days most likely to be below zero are in January. How does one keep hydrated on a long ride?

While it is possible to have afternoon temps in the 30's and 40's, a good many of these days are rainy.

Rain takes heat from your body at an alarming rate, particularly at cool temperatures. While I drove to work one day this January (and rode the remainder), it was when the forecast called for the rain to turn to ice by 3PM.

There is comparatively little daylight. Here, about 250 miles southish of Chicago, sunrise at 8, sunset a little after 5. Not a lot of margin for long days.