Jack, just wow. Thanks a million for the great information! You've given me a lot to think about. Right now I'm seriously considering heading down Hole-in-the-Rock Rd. to the primitive camping area near Sooner Rocks. There's also camping allowed in previously disturbed areas within 50 feet of the road along FR260, FR275, and FR280 as alternative options, as is the Cutoff Road near Little Death Hollow that you pointed out. Since I'm going to be there for four days and nights I'd rather set up a camp than try and poach something sleeping in my vehicle. From what I can see on the chart, the whole chunk of territory along Hole-in-the-Rock Rd. is in a black zone.
The area you mention north of Boulder sounds VERY tempting, but at 9500 feet it's gonna be c-c-c-old up there. Probably too cold for my thin desert rat blood this time of year. I'll definitely keep it in mind for early summer though. For this trip I think I'll try to stay below 5000 feet.
Once again. many thanks for the benefit of your years of experience in the area. It's obvious that you love the place. Although I've been to Moab and Canyonlands many times this will be my first visit to Escalante and I'm really looking forward to it.
Excellent advice from Jack, there. Not too much I can add.
Sounds like your wanting to get off the main roads, so that eliminates a few of my ideas, such as Head-of-the-Rocks scenic overlook (about 5 miles north of Escalante), the Hogsback (a couple miles north of Calf Creek campground), and 2 of the 3 scenic overlooks going over Boulder Mtn... Steep Creek (?) which I believe Jack was referring to and Larb Hollow, which is further north, toward Torrey. (You can see the La Sal Mtns, east of Arches, from the latter - roughly 130 miles away!) These are all places you can/must see during your daytime hours.
Be sure to check on current road conditions. I read that Hole-in-the-Rock Road incurred major damage in the epic rainstorms we recently received. There may be others. Hell's Backbone is always a rough ride, but it's namesake Grill in Boulder is *highly* recommended, if you've got the cash to spare.
About 6-8 miles east of Boulder, on the Burr Trail, is a primitive campground amidst some lovely Junipers on the north side of the road. I've been wanting to try a couple nights there sometime. It's just before you start to drop down into Long Canyon, which is awesome to drive through. The Capitol Reef end of that road is amazing too, with steep switchbacks descending down the Waterpocket Fold and the Henry Mtns towering up in the east, beyond Strike Valley.
I'd urge you to set aside a little time for Capitol Reef while you're in the neighborhood, but then I'm somewhat biased!