What highway would be the biggest pain in the ass to clinch?

[hobsini2]

I would imagine trying to find the routing of all the Dixie Highway segments would be a pain in the arse.

A couple on the state level that come to mind because of length/time, access, lack of signage or changes of direction:

WIS 35 East Dubuque IL to Superior
WIS 23 Darlington to Sheboygan
WIS 32 Pleasant Prairie to Land O'Lakes
ILL 1 Cave In The Rock to Chicago

I have the Saginaw Trail down pat but don't know where in Ohio it starts and ends. I've seen it in Kentucky.

And did you know that there is a Dixie Hwy segment (signed still) into Chicago?

[hobsini2]

I would imagine trying to find the routing of all the Dixie Highway segments would be a pain in the arse.

Twenty years ago, yes.
Nowadays, not so much.
https://2lanetraveler.com/home/dhmaps/

Thanks for this.

[Flint1979]

I would imagine trying to find the routing of all the Dixie Highway segments would be a pain in the arse.

A couple on the state level that come to mind because of length/time, access, lack of signage or changes of direction:

WIS 35 East Dubuque IL to Superior
WIS 23 Darlington to Sheboygan
WIS 32 Pleasant Prairie to Land O'Lakes
ILL 1 Cave In The Rock to Chicago

I have the Saginaw Trail down pat but don't know where in Ohio it starts and ends. I've seen it in Kentucky.

And did you know that there is a Dixie Hwy segment (signed still) into Chicago?

Yup I'm aware of that one as well.

[Henry]

I'd say any highway with gaps that indicate it will be extended in the future, such as I-69 and I-74. The two I-76s, I-84s, I-86s and I-88s (plus the US 2s as well) are exempt from this because their gaps are too large for them to connect on their own, and therefore can be considered two separate segments.

[kphoger]

In Canada's or Alaska's northern reaches, is there any highway whose northern terminus is beyond an oil field security gate?

[Mapmikey]

Any long US highway with significant urban street mileage, would be just a miserable slog.

This is the truth...

I drove US 1 from New Brunswick NJ to Providence RI in one sitting....took about 8 hrs

[deathtopumpkins]

In Canada's or Alaska's northern reaches, is there any highway whose northern terminus is beyond an oil field security gate?

I don't think so. The Dalton higwhay (AK 11) ends in Deadhorse, about 2 miles shy of the gate. That's the only numbered one I can think of that leads to a restricted-access oilfield. The Tuktoyaktuk highway (NWT 10) leads right to the Arctic coast.

Plenty of those northern roads would be a real PITA to clinch though, due to extreme remoteness and poor road conditions. Some dead-end out in the wilderness with no services for hundreds of miles and likely single-digit daily traffic volumes. Plenty are also only maintained seasonally.

[Flint1979]

I don't think length wise this was a hard one but I clinched IN-42 last night. With all the curves and the narrowness of the highway it seemed like it took forever to clinch.

[kphoger]

YT-6 would be a PITA to clinch, although at least the portion beyond the YT/NT border is no longer a state route.  On the other hand, oscar actually clinched it back in 2012, over the course of two days (not counting return-trip mileage).