Most boring states for those into roads

[Alps]

I'm late to this thread, but this is based on my own experiences in our 50 states:
NC - Very boring. Old signs disappear rapidly. Button copy's gone AFAIK. Very few old highways - all of the freeways get upgraded with few exceptions. NC 147 through Durham and US 220 in Greensboro stick out. Most of my photos from NC are embossed white historical signs and the very occasional older, cracked shield.
VA - Mostly boring. Never used button copy, at least that I've seen. Also very few old highways. The saving grace in VA is the independent cities. Just like in VT, when cities maintain their own roads, you get a lot of treasures by poking around. VA has cutouts and/or non-cutouts in various states of ancientness. There are also a fair number of interesting old alignments in hilly areas, but most of them don't yield fruit.
MD - Somewhat boring. Although I enjoy driving in the state, I realize that most of the routes are well signed with modern signs, well designed with few old stubs. Baltimore is the notable exception, but it takes up a significant percentage of the entire state, so it helps weight the average. Also, all of the old alignments are retained as state highways, giving the roadgeek something interesting to do to get off the boring main highways.

There are many states between the Rockies and {the row of states just west of the Mississippi} that I can't rate, having only explored a few roads, but given the long distances between just about anything, I'd have to say they're all boring for the most part. The scenery is beautiful, but the roadgeekery just doesn't present itself.

[hbelkins]

Kentucky's big attraction, to me, is the difference in signing practices for route markers between the 12 highway districts.

Most of the old signage is gone and I really can't think of anything in the state that stands out otherwise.

[agentsteel53]

Also, all of the old alignments are retained as state highways, giving the roadgeek something interesting to do to get off the boring main highways.

I would claim the exact opposite.  old state highways that are demoted to town/county control are the best for finding decrepit matter that just was never replaced.

[Laura]

Also, all of the old alignments are retained as state highways, giving the roadgeek something interesting to do to get off the boring main highways.

I would claim the exact opposite.  old state highways that are demoted to town/county control are the best for finding decrepit matter that just was never replaced.

Maryland has fine examples of both.

I wouldn't call Maryland boring at all as far as roadgeeking goes. Baltimore, like you said, is a treasure chest. Button copy, old signs, route weirdness, stubs, highways to nowhere. Delmarva has a lot of what I call "quintessential Maryland roads" with old pavement, stubs, bridges, almost ghost towns, and unusual signage (not old, just unusual). Western Maryland has covered bridges, awesome old national road switchbacks, old signs in some of the towns, the Sideling Hill cutout. Statewide, there are weird indeterminate points for state/county maintenance, plus lots of state routes that "dead end" into the bay.

Also, lol at "well signed with modern signs". Some sections are signed obsessively while others are hardly, if signed at all.