Anna Cummings
Welcome
Cummings Eventing is a small, private training operation based primarily out of Fort Collins, CO. Our main focus is Eventing with a strong focus on developing strong foundational skills to achieve goals while being safe and maintaining the joy of our sport.
About Anna
Anna Cummings is the head trainer and founder of
Cummings Eventing. She is a 2* event rider with big dreams
and an even bigger commitment to her horses, her students,
and the sport she loves.
Anna rides and trains out of Windholme Farms. She offers
a well rounded training program for horses and riders in the sport of Eventing.
From a very young age Anna knew that horses were going to be a part of her life. She has found her passion in eventing and currently has experience competing through the Preliminary level and 2* Level. Her mother is a very successful dressage and event trainer and her father spent many years training and instilling confidence in young colts. Between the knowledge inherited from both parents Anna believes that not only does it take skill and experience to become a good rider, but it also takes good horsemanship.
Having started teaching professionally over a decade ago at the age of 16, she believes in the importance of the dressage/flatwork and finds joy in designing a program the uniquely suits each horse and rider. Anna has experience working with a wide variety of horses and riders. Whether you are looking to just improve your riding or want to compete seriously she would love to help you reach your goals. She also loves working with beginners.
Anna believes that there is always more to learn and therefore is always striving to increase her expertise. For the past 13 years she has trained under two time olympian and past olympic selector Julie Richards. From a year spent as a working student to now basing out of Julie's farm for a month every winter, Anna has found her mentorship invaluable. Anna has also spent time taking lessons with other experts such as Olympian Phillip Dutton, Olympic coach Captain Mark Phillips, Olympic show jumper Lauren Hough and Grand Prix dressage rider and judge Jessica Wisdom. She plans to test for her ECP certification in 2026 and loves bringing in outside clinicians for her riders to glean wisdom and knowledge from.
Accomplishments:
2021 USEA Reserve Leading Adult Rider Training Level
2021 Area IX 3rd Place Leading Adult Rider
2021 Area IX Reserve Training Champion
2022 Area IX Reserve Preliminary Champion
2022 Area IX Reserve Training Champion
2022 Area IX Reserve Novice Champion
2022 CCI 2* 8th Place Finish @ Aiken, SC
2024 5th Place Finish Preliminary @ Skyline, UT
2025 9th Place AECs Novice
Clients
We’re proud of the community we’re building here at Cummings Eventing. Where riders feel supported, horses are well cared for, and progress feels exciting (not overwhelming). Our clients come from all backgrounds and riding levels, and we love watching them grow in and out of the saddle.
Here’s what some of them have to say about their experience riding, training, and being part of the team.
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Alexandra Jenkins and Peanut
Anna is truly one of a kind. She is supportive and kind while also knowing just when to push for more. Being a part of the Cummings Eventing team has really been a blessing.
Lindy is also so kind and knowledgable. Its such a gift to have both of them to learn from. Everyone at Cummings Eventing is welcoming and supportive. What a great team to be apart of.
Jennifer Bauer and Eric
Joining Cummings Eventing changed everything for me. I came in with a green horse and very little confidence, and Anna met us with patience, kindness, and endless support. She teaches with heart, and a deep respect for both horse and rider. Lindy brings precision and strategy, helping me unlock things I didn’t know were possible. Together, they make a powerful team. Whether you're jumping for fun or chasing big goals, you’ll feel seen and valued here. It’s the most fun I’ve had on a horse in years.
Tessa, Bea, and Nikki
As a parent, we gravitated toward Cummings Eventing because of its word of mouth reputation. We heard that it was a kind, nurturing environment for rider and horse.
Anna has an extremely positive coaching approach. She is extremely knowledgeable and hardworking. Her expertise is priceless and she is very detailed in her coaching.
Navin Ranweiler
My experience with Cummins Eventing has been incredible. I’ve grown so much as a rider and since I’ve joined their program.
As a trainer, Anna tries to bring out the best in both you and your horse. She will always work with you to get closer to your goals whatever they are. It’s such an incredible and fun community that wants to see you crush it! No matter what your goals are, the crew is there to cheer you on. I’ve learned so much from Anna and Lindy and can’t wait to learn more.