Well, I won't know the last three until it's done, but as for the first:
I'll start off in my hometown, the good ol' Northern Virginia Urban Conglomerate (I've always found something vaguely grotesque in that word, "conglomerate." Have you?). From there I'll pop up into Pennsylvania, Maryland, and West Virginia in quick succession (following the light-green arrows), then work my way down the southern Appalachians through Virginia, Kentucky, Tennessee, the Carolinas, and Georgia. After that I'll head south to Alabama, then all the way down to Florida (where I expect I'll linger for a few days on the beach), then back up to Mississippi, and then over the river to Louisiana.
The path splits there, and it's all Illinois' fault. Their high point is on private land, you see, and those landowners only allow highpointers to visit their property on the first weekend of each summer month. This puts an awkward constraint on my trip: I need the Southern portion to take exactly one month and three days, putting me in Illinois on June 4th. I highly doubt my original plan, following the light-green arrows from Louisiana straight up to Arkansas and Missouri, will take that long, so I'll probably end up detouring through Texas to kill time and shave a few miles from the Western leg. I've heard that Guadalupe Peak is best visited in the spring and fall, anyway.
After the Ozarks and Illinois, I'll swing home by way of Indiana and Ohio, then head up to Delaware to begin the Northern third of the trip (shown in dark green). I don't expect New Jersey, Connecticut, Massachusetts, or Rhode Island to be too terribly taxing, but Maine's Katahdin will pose both a physical and logistical challenge due to Baxter State Park's remoteness and somewhat draconian reservation system. I hope I'll be able to camp in the park, but I might have to settle for a day-use permit and a distant hotel.
However that goes down, I'll next revisit Mt. Washington (minus the ice, God willing) in New Hampshire, then hike the high points of Vermont and New York. After that I'll swing around the Great Lakes and up through Michigan, then on to Wisconsin, Minnesota, and all the way to isolated little Iowa.
The real fun starts on the Western leg of the trip. First I'll cross the plains to the Dakotas. ND's White Butte is a bit underwhelming, but South Dakota's Harney Peak is a real mountain. I'll snag Nebraska on my way south to Colorado's 14,440-foot Mt. Elbert, then pick up Kansas and Oklahoma on my way to Wheeler Peak in New Mexico. It's all high mountains from here on out: with luck I'll be able to climb Arizona, California, Nevada, Utah, and Idaho's high points in the snow-free days of late summer. That is, if I'm allowed onto Mt. Whitney at all: the high point of both California and the lower 48 sees so much traffic that all but the least-popular and most-circuitous routes up the mountain are heavily restricted. I could have applied for a permit back in February if I'd had my plans together, but as it is I'll have to hope they can squeeze me in sometime in late July.
As for the last four, linked with purple arrows: those peaks require extensive backcountry travel, snow/ice climbing gear, or both to summit. I don't yet have the skills or the gear to go them alone, but if I happen to meet some fellow highpointers who don't mind me tagging along, I might give them a try. We'll see.
So that's basically it. I'll end up in Washington state with, if all goes well, over 40 peaks in my bag and tons of stories to tell.
Now hopefully those Lar--erm, mutant mountain groundhogs--will quit complaining about the lack of diversity in their rock menus.
I'm heading out today! Wish me luck!
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