Adventures of Riley Madison

02/16/2026

For Valentine’s Day, my dad surprised my mom and me with the sweetest night out 🖤 We went to see Hadestown off Broadway. It’s considered to be “the greatest love story ever”. Hadestown

It was storming and we almost didn’t go, but my dad insisted on making it a special night. We had no idea where we were headed, which made it even more fun. Every single moment was amazing.

And of course, we didn’t just see the show… he waited with us so we could meet the cast after!! I had the best time.

Thanks for always setting the standard high dad! John T Boston II Go Go Chic

02/08/2026

Never forget…

12/25/2025

Giving the halter new meaning, but he’ll never be replaced. 🐴

12/10/2025

This is Crumble, he was one of my favorite pets! My Pop-Pop hated seeing him when we were on FaceTime , so he would hang up if Crumble came on camera. 😂😂😂😂 And I don’t know why I put him in a dress…🤷🏽‍♀️🤦🏽‍♀️

10/08/2025

(Sorry… the music got deleted.)

I got him in September 2024 — a rescue, still learning to trust the world again. I spent months bonding with him, loving him, earning his trust. Just a few months ago, he was finally ready to be ridden, and I was so full of hope for everything we were going to do together. The dream was real.

Then came the unthinkable.

He was diagnosed with a neurological disorder. After a second opinion confirmed it, I had to make the hardest decision of my life — to say goodbye.

Our last days together were precious. Our final moments, devastating. I held him close as my heart broke in a way I never imagined possible. The toddler girl in me — the one who dreamed of rodeos, trail rides, and growing old with her horse — is mourning a dream that ended too soon.

We never made it to the arena. This condition was a ticking time bomb, and it could’ve hurt us both if it showed up later. As hard as it was, I know I did the right thing for him.

As we said goodbye, a ladybug landed on him — small, quiet, and somehow perfect. In that moment it felt like a reminder of how special he was and how much he meant to me.

Goodbye, sweet boy. No more pain. Just memories of soft noses, warm eyes, and the bond we built together.

You were my dream come true, even if only for a while. 🤍🐞🐎

08/14/2025

06/19/2025

Today I rode with my riding club down the streets of Chicago. Thank you Broken Arrow Horseback Riding Club and Murdock Murdock for keeping the culture!

Each year, Black people across the United States observe June 19—the day in 1865 when thousands of formerly enslaved people in Galveston, Texas, learned of the Emancipation Proclamation. And each year on Juneteenth, Black cowboys throughout America saddle up in places like Chicago to commemorate the freedom message that came in on horseback.
Often accompanied by food and music, these events echo the celebratory atmosphere found in many Black communities on the holiday. They are also a reminder that horses are intimately tied to the histories of Black freedom and survival at the heart of Juneteenth.