Something vaguely similar in concept though substantially more brutal was undertaken in the past.  From the Northern Minnesota Track Club vault:  
Not all of the traditions of the NMTC have stayed as true as the fall series and the MVTR. Few souls in the running world can say that they have entered or completed the Tischer Creak River Run (TCRR). This WAS a spring event during the 80's that was run during finals week at University of Minnesota-Duluth from the Woodland neighborhood of Duluth. The run wandered down to Lake Superior where the brave souls began their pilgrimage up the creek with their sights set on the dam at Hartley Field. This was not a run that was to be won but rather survived as the body went up against Mother Nature and whatever may have collected in the creek over the years. All bets were off in the TCRR as the runners neared the finish. While the run itself took over three hours, the real pleasure came as the runners had to scale the sixteen foot tall dam at Hartley Field. The trick is that the runners could only use what they had picked up along the way to get over the dam wall. In 1986 Gunnar Nelson made it to the dam alone, after his three fellow competitors dropped out. He did not make it over the dam!
I think you have a good idea, although the idea of hammering uphill all the way is making me hurt already.  I'd suggest talking to Gene Curnow, who ran the NMTC races for many years, or to Eve Stein, who has put on a number of successful races locally in recent years.  One problem I could foresee with your proposed route is that a big event on that route would involve a lot of traffic disruption, and the city might not be all that receptive to providing the police presence that would require.  Whether a smaller-scale under-the-radar affair might work, I don't know.  I'd run it though.

superior to skyline could easily be done via 14th and chester...and because most cross streets from the lake to chester are one way, holding up traffic would be that much easier.

still...a Duluth Hash kennel would be a good thing.

I've been backing a relay race along the entire Superior Hiking Trail. There's a similar race in Oregon (and elsewhere, I'm sure) and our route would help promote this outstanding local resource.

A Skyline Marathon (any 26 mile length of Skyline Drive) would also be awesome.

A relay race on the Superior Hiking Trail... or even Skyline Parkway... that sounds cool. Maybe I'll put the hill climb on the shelf and back that idea. Are there any notable relay races around the Northland?

The best race I've ever been around was a relay race - the Klondike Trail of '98 International Road Relay. About 100 miles up and over the mountains and the international border from Skagway, Alaska, to Whitehorse, Yukon Territory. 10 stages. Run overnight. Awesome: http://www.klondikeroadrelay.com/race2/

I like the idea of a relay along the Superior Hiking Trail, but not necessarily a race. I think it might be better as an exhibition. 

Instead of passing a baton or torch, perhaps there's something symbolic or humorous that could be "delivered" from Jackson Lake to Duluth by a group of runners.

(Although the trail doesn't totally connect Duluth to Two Harbors yet.)

When I was in high school, I once participated in a sprawling Capture the Flag game held on a large acreage in the woods. My strategy was to circle so far around that I would never be detected by the enemy. I walked through the woods for a long time. I eventually was drawn back to camp by people calling my name.  The game was over.

I would suggest holding Capture the Flag games in the Spirit Mountain/Magney Park area, but if anyone thinks I'm going to organize something like that, they can think again.

The runners should deliver a carton of Kools. Have a grateful recipient waiting at the finish line.

Superior-to-Skyline Tunnel Run!

Your idea reminds me of your post about the basketball rolling and bouncing down the street. Imagine the carnage of a downhill race.

Not at all, I guess I was the one who was going off topic.  Good list, Paul.

I get the appeal of running up Lake Avenue.  It would be a really short run though, the hill notwithstanding, and the logistics would be complex.  Here's another possibility [perhaps what Shane had in mind?]--from the mouth of the Lester River to the overlook on Hawk Ridge.  Of course if it attracts a crowd, you once again could run into some problems with parking at the start, shuttling people back down, etc.

As for wildgoose's first 6/16 post above, the Lake Avenue Downhill was not as fast as the planners thought. Snow was bad that year and they didn't have as much to work with for reducing the up/down effect at each intersection...
I watched it and it was another Duluth novelty. 
I saw Gremmels reply to another post.  He should know- I'm pretty sure he was in the event (I remember seeing him come up to Chester Bowl in his full downhill gear...sweet helmet!).