Route planning

So I have a week, and don't have much of a plan yet. I have 3 main starting options to choose from, and a bunch of variables. Since it is now pretty much certain I'm the only one going this year, it's all up to me.

1. Ride to NYC on the afternoon before Moto2our officially starts. Stay over night (Eric- I haven't asked you about this yet. Expect me to.) Then go from there to Montreal on day 1.

Gets me a little head start. Gives me the weekend in Montreal, where people are lining up fun stuff for me. Avoids the miserable Toronto - Montreal ride on the Trans-Canadian.

2. Same as above, but from NYC to Toronto on day 1. Then on to Montreal on day 2.

Now this option is only in play if a friend of mine is going to be in Toronto. Whip-smart, fun and knows art like nobody else I know. Anyway, she moved from there a month ago, but might be back in TO when I would come through. If she's not there, I'll pass on it all together.

3. DC to Chicago on Day 1. Then Toronto then Montreal.

OK. Now this could be fun. I could get to hang with Meredith, which I would love. I'd also get a chance to do my longest day ever on a bike. I could add Indiana, Illinois and Michigan to my state list. And I could add Kalamazoo to my list of "Places I've been with funny names that everyone has heard of but no one has ever been to or could point out on a map". (See also: Schenectady, Punxsutawny, Walla Walla, Yonkers, Ohio, etc.)

This could also be hell. 750 miles in one day. All interstate. 12 hours actual riding time. 15-16 hour day with stops. Keep in mind that my 2 longest days ever have been 532 miles (Minitour July 4) and 530 miles (Mototour06). I was very tired, very very tired, after both of those. And that was only 11 hours of riding. This also means a day from CHI to TO and a day from TO to MTL. Which starts cutting into my Bar Harbor and Cape Cod time. Ahem.

Brian thinks this idea is insane. I think, how insane can it be if it wouldn't even qualify you for the easiest, most basic, Ironbutt award?

As for the rest of the trip, it's hard to say what days I'll be where, but here's a rough outline of places I think I might hit.

Chicago?
Toronto?
Montreal
Side trip to Nova Scotia? (Adds Nova Scotia, New Brunswick and P.E.I to the list of "states")
Maine coast and Bar Harbor for R&R
NH and Vermont for some Green and White Mountain riding.
Western Mass and Conn and RI on my way to Cape Cod. More R&R.
NYC to visit with Eric and day ride out to Hamptons/Montauk.