John Wayne. My dad and I loved watching True Grit, the original movie starring the late actor. I have the greatest memories of my father, so I named my horse True Grit (with a barn name of “Duke”) and I think riding with John Wayne would be fun and sentimental—plus make my daddy proud.

Susan Savage, Nevada

Walter Pruit, aka “the Old Man” in author and clinician Mark Rashid’s books. I’d join him on a ride through Rocky Mountain National Park, ask him a question about trail riding, and listen carefully to the flood of wisdom that would pour forth.

Steve Nickel, Colorado

Fallon Taylor. She’s my barrel-racing idol. I’d love even just to have a conversation with her.

Evelyn Gilbreath, Missouri

My grandmother. About 80 years ago, my grandparents rode from New Hampshire, where I live, to upper Vermont, where my grandmother grew up. If I could take anyone with me on that same journey, I’d take my grandmother, who’s now 98 and suffering from dementia. I will make this ride someday.

Amy Basch, New Hampshire

Roy Rogers and Trigger. If they were already busy on a trail ride with someone else, it’d have to be Wilbur and Mr. Ed.

Ron Henroid, Missouri

Percy Jackson. Fictional hero of the book series Percy Jackson & the Olympians, he can communicate with horses, so he could tell me what my horse is thinking. That would be fun!

Kendal Stokes, North Carolina

Tom Selleck and Sam Elliott. I’d put one on each side of me, and hope that by the end of the ride, we’d be friends and I’d know more about them than just their public personas. (By the way, their wives would be welcome, too—I think they’re amazing in their own careers.)

Debra Prychun, Oregon

Crazy Horse, the Native American war leader of the Oglala Lakota and a superb horseman. The trails he’d take would be beautiful and breathtaking. He’d also love my Arabian gelding, Lakota, for his beauty and endurance—and for being named after the tribe.

Mary Mott, Minnesota

My daughter. We used to ride every morning at 6:30, she on Freckles, I on Willie. She’s now away at college, and trail rides are rare. Both horses have crossed the Rainbow Bridge, and I miss them, our rides, and my daughter.

Tammy Bailey, South Carolina

Former President George W. Bush. I’d thank him for his service, then ask him about his best memory and the hardest decision he made as President. I think he—and the Secret Service!—would make awesome trail partners.

Mary Lipginski, Kentucky