Going out on the trails has always been one of my favorite things to do with my horse. There’s just something awesome about going for a stroll in the woods tucked away in nature with good people and good ponies, that make it both relaxing and really fun.

But there are a few things you need to have before you can relax and enjoy those trail rides: you’ve got to be able to trust your mount and have a lot confidence in yourself. And I’ll tell you one thing for free: that often doesn’t come quickly or easily.

For me, it’s taken the better part of a year to reach this point with my 8 year old off track Thoroughbred. I’m sure a lot of people more experienced than me would have had no problem taking him out on the trails sooner, but guess what? I’m an adult amateur. I’m no professional but I am absolutely game for hard work. We’ve put in loads of arena time, worked around cows, walked through a mounted police de-spooking clinic, and worked our butts off to build a relationship.

Even with that effort, he’s still a little green and occasionally makes it a point to prove some OTTB stereotypes — hot headed, pushy, maybe a little jumpy or reactive at times.

Blame it on the collective inexperience of my horse and I (and there’s nothing wrong with that) but there’s only one solution to make progress and get where you want to go: time and practice. Time to build a trusting relationship, to be exposed to all the things that might scare us, and practice at managing our reactions and being an upstanding citizen when things get uncomfortable for either of us.

Make no mistake — I’m a better rider and trainer and he’s become a better horse because of this time, practice and flat out work.

So last Saturday, 9 months after retiring from the track, I took Indy, the racehorse formerly known as Sure Prize, on his first long trail ride with great success.

On the trails behind our farm, we went out with my fiancee Lisa and our friend Tracy, with Indy and I sandwiched in between two experienced horses and riders. Despite a few challenges at the beginning (we jumped a little stream because it wasn’t water, must have been lava) Indy was almost a perfect gentlemen for the entire ride. We spooked once on the way home at a snap, crackle, pop in the woods but it was enough to startle the other horses we rode with too. All three horses turned on their haunches, did a complete 180 and came to a standstill in a split second. We’d moved a total of maybe 2 feet. No bolting, no bucking. Indy stood with the group after a sketchy few seconds and I have to say, I was thrilled with that response.

Why? Because even though he spooked, he didn’t let his mind literally or figuratively run away with him. He didn’t make up his mind to run home or act like a complete fool. He stood with the other horses, maybe a little skeptical, but trusted me enough to determine the best course of action.

A few summers ago I was hitting the trails with Lisa just about every weekend in the woods behind our farm. We’d go off for a few hours at a time, covering anywhere from 4-8 miles with her horse Gypsy and my horse Bob. It was a weekend ritual that I looked forward to every sunny Saturday & Sunday.

Then I had to hit the proverbial reset button when my buddy Bob, the first horse I’d ever owned and loved, pulled up lame. In one trip to the clinic, my trusty buddy Bob retired to pasture puff and I started all over again with Indy last August.

I still get choked up at the idea that I’ll never ride my buddy Bob again, and maybe someday that will change. But if we’re being completely honest I got just as choked up when Indy and I strolled back on to the farm, safe and sound from our first trip out on the trails. I hopped down from the saddle and gave my boy a hug around his neck and I couldn’t help the tears from forming.

We’d done it together and it was awesome.