Another Dion skipper (observation https://www.inaturalist.org/observations/189689470) at this location suggests this individual is probably also E. dion. But, the markings on the ventral wing look a bit different to me, so more input is welcome.

Observations entered for two of three individuals seen flying vigorously, chasing, and occasionally perching. This one was pristine, while the other had extensive wing damage (https://inaturalist.ca/observations/178606049).
Nectaring on White Clover (Trifolium repens)in Photos 2 & 3.

Seen only in the lowest section of the road, puddling on gravel. Also saw him briefly nectaring on clover.

Smaller than Dreamy duskywing. Wingspan approx. 30.5mm (used my finger for scale in ImageJ). Apical spots in a straight line suggests Columbine rather than Wild indigo duskywing.

was photographing the variety of insects drawn to the nectar of the milkweed - the flowers were fresh and scented and being mobbed.

I saw what I first thought was a wasp behaving rather oddly. It was not in constant movement on the flowers but hanging still from the underside of a leaf - the third image shows my initial view.

The second image was obtained by turning the plant leaf over - the insect remained still only twitching its antenna a trifle.

A second insect of the same type was found in a similar position on another nearby milkweed.

Alice Chambers Trail about 100 m east of Provincial Road 520. Uncommon and sporadic in Manitoba - fringe of range. Flushed and perched in tree about 10 feet (3 m) off ground; no chance of upper-side view.