I thought I’d toss this out there since western sidesaddle is a thing and I see it periodically, especially with the arabs. I am absolutely FASCINATED with side saddle. I’m looking for any resources regarding riding aside. I live in North Dakota, which is full of a lot of nothing so I doubt there’s anyone who gives lessons in within reasonable distance but if anyone does know, I’d love to know! Also any reading material, sale websites for saddles, etc. would be great.
You may want to ask on a more general stuff forum, maybe Off Course?
FB group Sidesaddle Riders! is a good resource.
For Western, even better than Sidesaddle Riders! for things like shopping/turnout is: https://www.facebook.com/groups/westernsidesaddlesociety/
A lot of the same people, but with a focus on western 
For techniques and how-tos, SideSaddle Riders! is a great resource.
And it’s super fun! I don’t have a western horse currently, but rode my last western horse aside quite a bit.
I live in ND as well. Have never seen or heard of anyone riding side-saddle, so you may be hard pressed to find lessons for such. But I would start contacting trainers, as they can maybe refer you to resources
You will want to decide if you want to ride an English sidesaddle or a Western sidesaddle in choosing your saddle to start. I do think the English style is more secure in letting you “hold on” because of that second horn over your left leg. You feel rather “locked on” with the leaping horn during a ride. I actually rode a few bucks with my horse and never felt the least loose in the English sidesaddle. She was rather “fresh” that day and I didn’t do her proper warm-up in my hurry to get over to the Sidesaddle Clinic riding part.
The single horn style sidesaddles are fancier, often quite Western in having double girths, bigger skirts, tooling. May also be called “Victorian” sidesaddles with plush fabric on seats, fancy stitching for decoration.
I had a Western sidesaddle that I learned to ride in, only one horn. I was told the one horn allowed easier escape if horse went down, which seemed more common in the rougher grounds of the Midwest and westward from there. It is true you can’t get out of the leaping horn of the English Sidesaddle very quickly!
From my experience, using my Western sidesaddle quite a bit to be a good sidesaddle rider, you will want to add a breastcollar, or hunting breast plate with the English type saddle. It prevents saddle sliding completely down the horse side if girth loosens during a ride. Try as you will, there is ALWAYS more weight on the saddle with both legs to the left side. Saddle will only slide offset a little ways, you can get out of trouble pretty easy from there, in either kind of saddle. I did riding down the roads and trails, getting in time to acclimate to the sidesaddle. Being practical on a Western style horse, I added the breastcollar to prevent problems.
I used a longer dressage style whip on the right, which replaces your lack of leg on that side. Length needs to reach the hind quarters. I wanted to be touching just behind the stifle, to enable clear direction to the well-trained horse on what to do with those hindquarters. No mixed signal when asking for a canter depart from a walk on the left lead or turn on the front or hindquarters when asked.
I personally preferred the English sidesaddle over the Western models. The Western types have a lot more “hard edges” you feel if moving or saddle is not exactly, perfectly your size. I especially noticed them when I got tired on long rides, so my body position wasn’t as good as it should be.
Be sure horse is well padded to protect his back from uneven weight of the sidesaddle. English model probably should be stuffed to fit you and horse. Size of seat is how long your hip to knee needs to be. Too short and knee is past the horn you hook it around so leg is on the area above tendons behind the knee. Plus you need a little seat length behind hips for posting.
Western sidesaddles don’t use posting because of no leaping horn, so length to fit is from back of saddle to where knee hooks around the horn. Don’t go too small, that hard seatback edge will get uncomfortable quite fast.
I replaced the stirrup that came with sidesaddle using a Peacock stirrup iron with rubberband side, for ease of escape if needed. The antique stirrups were MUCH to tiny for any feet belonging to someone over the age of 7yrs old. Quite dangerous to use tight irons, in case boots got stuck, so use a modern stirrup wide enough to get boot in and out easily. Some of those black colored stirrups in English or Western styles would look quite handsome on a sidesaddle.
This reprint book has a section with tips for and about female riders. Not very expensive. I found it informative, useful about the sidesaddle riding though I discarded things not pertinent to modern times. It was interesting reading on many horse uses, training, expectations of the finished horse!
Um, my western side saddle has a leaping horn… The leaping horn/no leaping horn is typically a question of when it was made, not the style. Every western side saddle I’ve seen in use has a leaping horn.
Please see:
http://www.sidesaddle.com/reference/saddles.shtml
http://www.sidesaddle.com/reference/saddles/GoodnightWesternSideSaddles.shtml
Wow, those are some nice Western sidesaddles. They do look newer, surely most were made more recently than 100 years ago. Where there is demand, someone will make the product wanted. Evidently modern women want leaping horns on their Western sidesaddles and got them made to suit themselves. Fine with me if they are happy! Nice to see those models. They just were not available in the past when I played with my sidesaddle riding. I could have gone for one of those and been quite happy!
Certainly not the sidesaddles that I have seen locally (Midwest area) or for sale in the past. Those were were all antiques. The antiques have never had a leaping head, mine included. Looking at old Sears Catalog reprints, there were almost no leaping horns on their sidesaddles in the “Western or Victorian” category.
I see sidesaddles at old farm auctions, most are junk, falling apart, not worth repairing. All are the Victorian types, no English ones among them. The Sears Catalog advertised them for sale cheap even back then, most probably under $25. Your links show a better class of saddle in leather and construction. They are not going to be inexpensive to purchase. Though compared to some name brand saddles mentioned here on COTH they are pretty cheap!
Not sure how pricy OP wants to get in obtaining a sidesaddle for fun riding. One of the reasons I mentioned sizing, was so she didn’t buy something totally unsuitably small that fit those tiny ladies from the past.
