Lessons

A woman in a purple shirt and riding helmet sitting on a dark brown horse with purple accessories, in a green outdoor setting with trees and grass.

Find Your Stride

Whether you're new to the saddle or returning after years away, Montana Calloway Bychurch offers lessons rooted in calm guidance, clear instruction, and genuine care—for horse and rider alike. Her approach builds confidence, skill, and connection, creating a safe and rewarding experience for riders of all levels.

Two young girls riding horses on a sandy fenced riding arena during daytime, with lush green trees in the background.

  • Tailored for Every Rider

    From first-time riders to those ready to refine their skills in the show ring, lessons are customized to meet individual goals and comfort levels.

  • One-on-One Attention

    Private and semi-private sessions ensure focused instruction and steady progress. Montana teaches every lesson herself.

  • Build Confidence, On and Off the Horse

    Lessons encompass everything from grooming and tacking up to riding and post-ride care, building knowledge, confidence, and a connection with the horse.

  • Peaceful, Professional Setting

    Enjoy lessons in a beautiful, quiet setting with access to well-maintained indoor and outdoor arenas, as well as safe, experienced lesson horses.

  • For Adults and Youth

    We welcome riders of all ages—from horse-loving kids to adult beginners or returning equestrians.

  • Start with a Trial Lesson

    New students are invited to book a one-time introductory session to experience the Mylestone approach firsthand.

Person riding a horse over a jump during an equestrian training session on a sandy arena, with green trees in the background.

Lesson Offerings

We offer a couple of lesson formats to suit different riders and schedules, all taught in a safe, laid-back, and welcoming environment.

  • 30-minute one-on-one sessions

    • Focused, individualized instruction

    • Ideal for beginner to advanced riders

    Rates:

    • $75 Trial Lesson (for new riders only – payment due before your visit)

    • $300/month for weekly lessons*

    • $80 for single private lessons (availability may vary)

    • Sibling/family discounts available

    Monthly payment is due by the 1st to reserve your time slot. A $10 late fee applies after the 1st.

    * The monthly commitment includes 4 (and sometimes 5) lessons (once a week). In other words, on the months your lesson day falls 5x instead of 4, the 5th lesson ends up being free!

  • 1-hour shared sessions

    • Ride and learn alongside another student

    • Ideal for riders with some experience or those who enjoy a group atmosphere

    • Inquire for pricing and availability

  • 15-minute guided pony rides

    • Perfect for young children or new horse lovers

    • $40 per ride

    • Payment due at time of ride

Lesson Commitment & Payment

To provide the best experience for everyone, we encourage riders commit to a month of weekly lessons at a time. This ensures consistency, helps with planning, and supports your rider’s steady progress.

  • Monthly payment is due on the 1st

  • Single lessons may be available depending on the schedule

  • We accept cash, check, Zelle, and Venmo

  • $10 late fee applies for payments made after the 1st

To learn more about lessons and payment, download our Lesson Policy & Payments PDF below.

Lesson Policy & Payments PDF

  • “I’ve been riding with Montana for about 13 years, and I truly can’t speak highly enough of her. I started taking horseback riding lessons when I was six, and everything I know, I’ve learned from her. She’s the best instructor anyone could ask for—steadily building my confidence and deepening my knowledge over the years. Beyond her talent and expertise, she’s a genuinely kind and caring person who truly looks out for her clients. Montana has become like family to me, and without a doubt, she’s the best trainer I’ve ever met. I couldn’t recommend her more.”

    Morgan Capone

  • "After decades in the saddle, I didn’t expect to feel uncertain again. But that’s exactly what happened when a well-intentioned move turned into a setback. The overly cautious environment left my horse and me with shaken confidence. Then I met Montana. Once we moved to the barn where she was training, everything began to turn around. From the start, she brought patience, kindness, and just the right amount of challenge. She helped us find our footing again—literally and emotionally. When she opened her own barn, there was no question—we were going with her."

    Cate French

  • A brown barn with white windows and a double door, surrounded by green trees and grass, with a small flower bed and statue in the foreground.

    Facilities

    Set on the former Huntingtown Farm, the serene environment and natural beauty of the property set a calming tone for horses and riders alike. With multiple barns, large turnouts, and a perimeter trail, it’s a hands-on, heart-forward facility where horses and riders feel at home.

    Learn More
  • A brown horse looking out of a stall window with white trim, inside a barn.

    Boarding

    Your horse’s well-being is our top priority. That’s why Mylestone Stables offers multiple levels of full-care boarding, tailored to match your horse’s specific dietary and daily needs. Each horse is treated like one of our own—with attentive care, consistent routines, and a welcoming environment.

    Learn More
  • A woman training a horse in an indoor riding arena with a dirt floor and a high, arched ceiling.

    Horse Training

    Montana offers gentle, consistent training that helps each horse gain confidence and learn at their own pace. From groundwork to saddle work, training is rooted in trust, feel, and the long-term well-being of the horse.

    Learn more

Get In Touch

Interested in a tour? Have questions? We’d love to show you around. Fill out the form to send a message directly to Montana. She’ll be delighted to hear from you and will be in touch as soon as possible.