Riding of any kind can be an opportunity for building relationships. There’s usually an element of being captive for hours of togetherness. I’m thinking of the road trip I took with daughter Esther from Atlanta to Seattle, in a small SUV packed to the roof with the remains of a household and two large dogs. It was epic.

And epic is my favorite word when it comes to activities that build relationship, because the more epic it is the more memorable. At the end of an epic event, I am usually bonded for years to come with my companions. This was definitely the case in my ride across the state of Florida with daughter Julia, on horseback. It was the Cracker Trail Ride of 2007. Epic.

The Cracker Trail was the route that Florida cowboys drove cattle to the Gulf Coast for shipping in the late 1800’s. Central Florida has a large cattle industry even today so there is lots of interest in keeping history alive with the yearly Trail Ride. The route is 120 miles.

I tried to do this ride in 2006 on a borrowed horse and only got about a mile from the start when the horse insisted on being the first in line (not allowed), and seized up when I wouldn’t let him. He was an old race track pony horse and just couldn’t understand that trail ride business. He got put in a trailer and taken back. I was disappointed.

The next year I had my own horse, Andy. Julia had one of her horses, Fea. We had a two horse trailer and a fancy black truck to pull it. We, and a couple hundred of our friends and acquaintances, spent the next five days riding from Bradenton, Florida to Fort Pierce on our horses. We camped in tents at night, in the fields of some of the large ranches in central Florida. There was a chuck wagon that served meals and usually some kind of fun activity or socializing each evening.

Every morning, after breakfast we would pack up camp, saddle up and ride until noon. At our lunch stop a bus would take drivers back to their vehicles and trailers. We would drive ahead to the next campsite and then take the bus back to the lunch stop, where we would again get on the horse and ride the rest of the afternoon. Logistically, it was pretty well planned. At times we rode on major highway right-of-ways, but often it was on ranch property.

Neither of us had ever ridden all day for five days in a row, so it took a day or so for us to get hardened in. We had been trying to get the horses ready for the event, but it was extreme for them too – not only the distance but the crowd of other horses, wagons, and road traffic. We (both us and the horses) were a little nervous the first day. Poor Andy got a red bow tied on his tail to warn others that he might kick if they got too close.

As I said, it was an epic trip for me. Having that once-in-a-lifetime adventure with my daughter gave so much opportunity to learn, to be challenged in our abilities, to succeed at something unusual. It was worth every minute, but it was hard. We were glad and ready to head home at the end of the ride.

Significant relationships are built in small ways, day by day, and that is great. But it is very important, when opportunity allows, to do something special. Maybe it is something challenging, or extravagant, or luxurious or as sometimes happens, something very miserable – but it will be memorable and talked about for a long time. Getting through escapades like this with your children adds so much to the relationship with them. You are investing time and money in an experience with them, and that speaks volumes. And the payback is pretty good – I wouldn’t trade my memories of that ride for anything.