Aside World Magazine

Winter 2020 Issue 

Riding Aside in an Astride World

To play, press and hold the enter key. To stop, release the enter key.

Article by Amy Jo McGee

Photo Credit Left to Right: Anne Gittens, Amy Drogoo, GRC photo 

Wondering what you can do to either gain more experience or further enjoy your time in your sidesaddle? The sky is the limit. While the number of shows that offer a dedicated side saddle division is limited, the actual opportunities are only limited by your imagination. There are many disciplines that are very welcoming of those riding aside. All of my experience is riding English, but I imagine there are numerous opportunities in the western world as well. Not ready to jump the USEF 3’ ladies sidesaddle over fences class yet? Or feel like you need more practice before attempting the 2’6” hack line at Devon? Load up your horse and your sidesaddle and head to your local hunter show! You can enter flat or jumping classes to gain whatever miles you feel you need. You may be the only one there aside, but I am sure others will enjoy watching you compete.


In my experience many of the hunter shows are more than happy to welcome you to their shows even in a sidesaddle. I have shown in several of the “regular” hunter divisions sidesaddle at numerous venues with nothing but encouragement from show management. This includes everything from Local Hunters at Devon to the 3’6” Performance hunters at the Brandywine Horse Shows, and even the National Hunter Derbies! My big goal is to participate in an International Hunter Derby aside. Working hard to make that goal a reality!!!!! But just like those starting out, I was a beginner once too, and jumping those first crossrails was just as hard for me as it is for you. You can do it! You do not have to wait for a show that has a dedicated side saddle division to get started.


Other disciplines are extremely inviting as well. While I only dabbled at dressage aside, having competed my previous mount Aaspen at 2nd level, Anne Moss has competed extremely successfully at the upper levels, and even earned her Silver medal sidesaddle. There are several ladies that I know of currently competing at the lower levels of dressage aside quite successfully. You could even go to a dressage show and ride one test astride and then switch tack and do a test aside. Just be sure to alert show management of your plans so they can schedule your rides far enough apart to allow for a tack change.


While not frequently seen, I know firsthand how much fun one can have eventing sidesaddle! The best thing about doing that is you can slowly build up by adding a phase in the sidesaddle as you feel ready. Your first event your goal could be to only ride your dressage test aside, then slowly work towards a goal of competing the entire event sidesaddle by adding phases as you gain confidence. I evented at Novice and Training level, all phases aside, on my horses Lady and Aaspen. I even placed at training level on Aaspen at the 2005 American Eventing Championships. I am always willing to answer questions for those wanting to give it a try. Some tweaking of the rulebook was necessary, but the president of the USEA was more than happy to help iron out the details to allow it to happen. Now the rules stand in place for others wanting to give it a go. I have had nothing but positive experiences when dealing with governing organizations regarding riding sidesaddle. The most important thing you can do is read the rule book of the discipline you wish to participate in. If an unrecognized show, many follow the rules and regulations of the national governing body. 


Other fun things are hunter paces, paper chases, and judged trail rides. While most of the other riders will be astride, you can still pack your sidesaddle and enjoy the experience aside. I encourage everyone to try something that you have always wanted to do. If your goal is to compete in dressage aside, enter a walk trot test at a local show and give it a try. The hardest step is the first one. Trust me, it gets easier! Check your tack well to be sure it is in good repair. Take a few lessons and get started. I encourage everyone to take advantage of sidesaddle instruction when it is available, but do not dismiss having a lesson with an instructor just because they do not have a sidesaddle background. Some of my best lessons have been in a sidesaddle with trainers who aren’t intimately familiar with these saddles. Go to camp and opportunities offered by ISSO for sidesaddle instruction, then fill the gaps with a local trainer you trust and supports you. I will be cheering you on! Stay tuned for future writings regarding sidesaddles and their unique features. Next issue I plan to write a piece regarding safety assemblies, their fittings, and how to measure for correct stirrup leather length. In between issues, feel free to check out my latest projects by visiting my sidesaddle Facebook page at


If you would like to submit an article for

an upcoming issue please email