If I time it right I can sneak out of Ontario on an above zero, dry road day. You can still find double digital daily highs in Cincinatti and south. A plugged in electric kit bonzai ride to Cinci and I'm out of the snowbelt. From there it's a less ragged ride south to New Orleans. From Cinci I'd angle over to Memphis and follow the Mississipi down to the Big Easy...
After reading books like Todd Blubaugh's Too Far Gone and watching Austin Vince Mondo Enduro the planet, I've often wondered what it would be like to get lost on the road. Once out of the snowbelt, I'd be in no rush to be somewhere. Without that very Western time fixation, I wouldn't have to get wound up over deadlines.
If I'm not fixated on a destination the daily goals might not be that linear. With local knowledge I'd hope to find things off the beaten path as I meander...
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After wandering Texas I'd take a run up to the Very Large Array in New Mexico and do my best Jodi Foster immitation. New Mexico and Arizona have a pile of strange sites to see, so the wandering would get intense. Norman Reedus did a Ride episode in New Mexico that does a good job of showing what's on hand out there.
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Tuscon is home of the Aeroplane Boneyard where thousands of retired air force planes sit in the desert. A wander around there at sunset would be a glorious thing. I've done the Phoenix area a couple of times and travelled from the north end of Arizona from Las Vegas, but haven't travelled as far south as Tuscon. From there I'd head across to Yuma, another famous western US location, before diving south into the Baja Penninsula. A desert riding tour would be a pretty cool way of seeing Baja.
Mexico is a whole other world. Most riding-the-Americas types blitz through it looking for a fast route south,but Mexico (with a final lunge into Belize) is where I'd wrap up this great escape from the never ending Canadian winter. Some crystal caves, Mesoamerican pyramids and Belize beaches during the deep freeze and then working my way back up to Austin for early April...
Seeing the Ozarks and the Tail of the Dragon during the weeks after the race would be a nice way to wind up this great escape, getting back to the frozen north just as it's not frozen anymore.