The British Pathé News site is a treasure trove of vintage films. I found this clip of a 1927 ladies’ point-to-point by sticking “sidesaddle” in the search engine, and what a sight it is. Frankly, much of the riding looks pretty awful!
The accompanying notes say there is no information on where it was filmed, or who is taking part. Women competed in open point-to-points from 1913 on, and the first ladies’ race took place in 1921. In 1929, the powers that be decided that they’d had quite enough of women beating men thank you, and they weren’t allowed to enter open races again till 1967.
Whew! You can see billows of steam rising from those horses!
Second and third look to have been riding side-saddle so they were effective, if not stylish! The woman holding the horse who won looks in a state of utter wretchedness.
I know! I could spend days on British Pathe news. Am going to put a link in your comments of a gymkhana.