Finally doing this route with nice weather made all the difference. In two previous attempts, the cold and intense wind kept me from finishing the route but not on this day. Temperatures were perfect (upper 30s Fahrenheit) for a wicking baselayer, a wind stopping jacket, thin running tights, and Runderwear's long shorts (under the tights to stop the wind); there wasn't much wind on this day, but being so close to Lake Michigan, it was still breezy. And in November, that breeze will be cold.
I started at the corner of Michigan St. and Art Museum Dr. since, personally, I think this is the best place to start. If you started anywhere else on this loop, this is the toughest 180 degree turn to make and ensure you've gone far enough to actually complete the route. The other 180 degree turn isn't far away, but it's a wider turn with better views and people expect others to make this turn. To avoid causing any collisions, I started at the aforementioned corner where I could also admire the Milwaukee Art Museum and its open wings. (This is another reason to do the route on a good weather day.) Despite the good weather, there were very few people out on the trail; the sudden drop in temperature from a day or two days previously seemed to keep a lot of people inside.
So few people outside meant fewer to dodge though and an easier run for me. I had my pick of where on the path to run, and I took full advantage when I got to Lincoln Memorial Dr. I had good timing with the traffic lights and prefer to run on the west side of Lincoln Memorial since it's not as heavily trafficked. This side isn't as smooth and will have puddles for a day or two without sufficient sun to evaporate it. Now with the leaves falling off the trees, you don't always know what's underfoot either. I still prefer the solitude of this side and not having to play Frogger later on.
Between the added effort of holding my pace up the ~5% grade of Lincoln Memorial and the (slightly) warmer temperature in Lake Park, I finally unzipped my jacket, pocketed my gloves, and removed my sweaty, fleece-lined headband. At least for a couple miles, I could enjoy this as I let my feet lead the way. Having done a couple recon runs, I learned the hard way that the Milwaukee County Parks' interactive website map contains a mistake in Lake Park, a mistake relative to the posted signage. To avoid this mistake, just follows the Oak Leaf Trail signs as you cross Ravine Rd. and Lake Park Dr.
I made it to the bottom of Lafayette Hill Rd before needing to zip my jacket up, put my gloves back on, and cover my ears. (I opted to pull my neck gaiter over my head instead of detaching my headband from where I'd clipped it into my hydration vest.) This was adequate for the last couple miles as this section is a tad farther from the lake until the final straight.
All-in-all a great run. Next time, I might try doing the loop in reverse to climb Lafayette Hill (~10%) and have a longer straight leading into the finish. That might have to wait until spring though because snow, ice, and bitterly cold, winter winds.
(One last thought: At the time of attempting this FKT, the public garbage cans (which can be found every half to a full mile along this route) are still out. I'm not sure if they will all stay out for the winter or if some of them will get picked up; I've never paid attention to them before in winter.)