Anna Cummings is the head trainer and founder of Cummings Eventing, where she combines over a decade of professional teaching with a lifetime of horsemanship.

A 2★ event rider competing at the Preliminary level, Anna is known for her thoughtful, individualized approach that builds confidence, connection, and clarity between horse and rider.

Raised in a family of trainers—her mother a dressage and eventing professional, her father a skilled colt starter—Anna’s philosophy balances classical foundation with modern feel. She has trained extensively with Olympian Julie Richards, and continues to learn from top professionals including Phillip Dutton, Captain Mark Phillips, and Jessica Wisdom.
 

Now also a mother, Anna brings a deepened sense of patience, balance, and perspective to her coaching. She believes growth in and out of the saddle go hand in hand—and creates an environment where riders of all levels can learn, progress, and truly enjoy the journey.

 Cece has been riding since the age of five, growing up in Pony Club with horse-loving parents and a deep-rooted passion for both horses and kids. She joined Cummings Eventing as a working student in 2019 and now serves as Barn Manager, balancing daily operations with teaching beginner lessons and helping to produce young horses. Her journey began with Ben, a QH/Mustang who introduced her to the joy of trail rides and schooling shows. She continues today with Mac (Fernhill Dreams Come True), a young prospect she’s bringing along from the ground up. Cece has competed up to Training level, has worked with top professionals and has earned top finishes throughout Area 9.

Known for her calm, kind energy and thoughtful instruction, Cece blends her natural teaching instincts with a love for inspiring young riders to build strong, safe foundations in the saddle.