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Anna Cummings

@cummings_eventing

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Christ follower // Wife // Mama // Equestrian
#kindnesswins
You’re far more capable than you even know ❤️
Let’s dream big together 💃
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This horse…this kid…this trainer…this team she’s gotten the chance to be a part of. The support she’s received from her sister. It’s all too much to put into words, full end of season post coming soon but til then…my heart is so fun and I’m so grateful for all of it!!!

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National Coaches day is October 6th. I thought this would be a great chance to share my two amazing coaches @cummings_eventing and Lindy. I am nearing my 4th year with @windholme_farm and it has been the most incredible experience. Anna and Lindy have helped me from learning how to jump, to entering horse ownership and taking me through my first show season. I couldn’t be more grateful for the confidence they have given me even when I didn’t feel like I could believe in myself. I seriously couldn’t do it without you two. 💕 #equestrian #horse #coach #gratitude

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the end to this amazing show season with all of the best!!! ❤️

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We finally did it. Countless shows and hours of (literal) blood, sweat, and tears. We crossed the finish flags and got to celebrate with @skipperdoodlefritz at the end (sorry you have to fear for my life, Jj).

I have so much to say, but in summary: I love this horse. I love my trainers. I love my team. To Anna, who came running the whole way from the start box when I crossed the flags to hug me and tell me you were so proud, I love you so much for you and your dedication to me, this sport, and my partnership with this horse. To Lindy, we’d never be here without that one day 2 years ago that you said “this is Echo, I think you’ll get along well”, thank you for believing in us and reminding me it’s okay to slow down. To both Lindy and Anna, thank you for telling me I could do it, even when I wasn’t so sure.

To the incredible team behind us who has believed in me when I was sure “if I don’t finish this time, I’m done” and signed up for the next show anyways, thank you for supporting my never-ending antics, and sending me and Echo all the congratulations this weekend. Even more, thank you for being at the trailer waiting with hugs all the times we didn’t complete. That mattered to me the most, and made celebrating with you so much sweeter.

To the kid in warm up who told me the yellow was the coolest thing they’d ever seen and that I looked like sunshine- you made my day, and reminded me why I decided to wear this color in the first place, and why I have kept wearing it when it would’ve been so much easier to blend in.

We got eliminated/retired/etc in XC at 7 shows straight and had countless XC schooling outings that ended in tears in addition to hard work at home before getting this. It takes time, and I’m so glad we kept going even when it was the hardest choice to make.

Echo Key, I love you. You’re the very best boy.

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Life Lesson number 498,734 as an Adult Amateur:
there is always Gratitude even in dissapointment.

Ive been meaning to recap The Event at Skyline for a while, and here we are almost 2 weeks later.

This was only our 4th shot together this season as we got a slow start due to my continued recovery both mentally and physically from my broken ankle last year. We qualified for the championship division from our first place at Archer and started out so well in the dressage!

18.5 is the lowest we've EVER had so I was trilled to come away from day one with a personal best and the top score.

Day 2 came and although we had 19 jumps that went so well, Peanut thought fence number 2 was too far away from her friends and tried to stop and go back home. We persisted, however and I rode the wiggly pterodactyl around the rest of the couse to complete a hard fought round.

Unfortunatly that took us from 1st to 9th. Honestly I was pretty dissapointed and it took me at least a week to embody all the things we say after a hard round....

She's sound and I stayed on.
Anytime Nutty and I get to show and ride together
is a win.
So many things went really right, and litterally
only 1 went wrong.
Best dressage test ever = win!
Fouth show, first long distance travel - its ok.
Qualifiying for Area 9 championships and just
getting there is a goal accomplished.

And day 3 we showed up and completed the event wih a double clear showjumping. It took me until jump 6 to really be in my body... but it got better and better - so I am grateful.

2 weeks later I have so much to be grateful for.

For my amazing teammates at Cummings Eventing, my phenominial trainer Anna Cummings, and additional rockstar traininer Lindy Weatherford. And my incredibly sweet friend Becca Caufield.

Grateful to the wiggly pterodactyl, aka Peanut who challenges me to show up better today than yesterday and always brings me back to gratitude.
She is the most amazing horse, really and gives her all for me everyday. I am grateful to her for allowing me to live my dream and the opportunity to keep striving for more.

Grateful to skyline eventing for a super show and all of Area 9!

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When your boy thinks meeting a cat is “exciting”. 😂

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Beat the bomb in Denver was a blast with our friends this Saturday. @miircreative welcome to your thirties! (again 😜🥳)

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A slightly delayed wrap-up from an incredible trip to Kentucky for the 2026 American Eventing Championships! 🇺🇸🐎

Coach Rebecca Caulfield, team members Tate S. and Logan O., and our beloved friend and fellow trainer Anna made the long trip east to Kentucky to contest the AECs.

We were lucky to have a wonderfully boring trip both ways, beautiful Kentucky weather, a great house, and some of our support team join us along the way. And, of course, we came home celebrating some pretty awesome results!

✨ Logan & Magic — 10th, Junior Beginner Novice + Reserve Champion TIP
✨ Anna & Prim — 3rd, Training Horse
✨ Becca & Horacio — 9th, Preliminary Rider

Tate had a great start out on cross country, but unfortunately had a tough go at the water and wasn’t able to finish her weekend the way she’d hoped. Results aside, Tate continues to be the definition of a wonderful teammate and horsewoman. She shows up for her horse and her team, through the highs and the hard days, and we absolutely treasure having her as part of this crew.

As a group, we couldn’t be more thankful to Ella and Molly for making the trip out to help, and to the entire village at home that makes adventures like this possible. It truly takes a team, and we are incredibly lucky to have ours.

So… is it too early to start setting goals for next year?

Let’s do it again. AEC 2027, here we come! 🇺🇸✨

#RebeccaCaulfieldEventing #TripleCreekEventing #USEventing #AEC2026 #Eventing

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Congratulations to McKenzie Spain & Anna Cummings, both finishing on the podium today here at the American Eventing Championships! 🥉 Our Novice riders will finish up with SJ tomorrow, while our Starter riders will tackle the XC. 📸 USEA

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No words for this incredible horse. Jumping better than ever, and finishing our AEC week with a smile. 💙 Top 10 is just a bonus.

So proud of you, H. What a horse. ✨

#rebeccacaulfieldeventing #AEC2026 #eventing #showjumping #FernhillOpulence

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