90-Minute Cowgirl: Horseback Riding at Deep Hollow Ranch

Gabrielle Payne has been around horses most of her life. That could explain how effortlessly she put a group of people, including me, who had no business getting on a horse, at ease as we climbed on the animals before a trail and beach ride at Deep Hollow Ranch in Montauk.

The niece of Cate Keogh, the current concessionaire at Deep Hollow Ranch, Payne’s love for horses was clearly on display as she hugged the face of this rider’s horse, saying he’s “such a snugglebug.”

Having someone so adept at calming the nerves of both the horses and slightly nervous riders was a definite plus because the last time I can recall being on a horse I was about 6 years old. Although more than a few decades have passed since then, my thrill genes are still intact, and I had recently added “going on a horseback ride” to my list of try-new-things. (Well, mostly new in this case). Some things on that list I can convince my husband to try too, and this one he gladly signed up for.

I’ve driven past the Deep Hollow Ranch more times than I can count, but I’ve never been tempted to turn into the driveway.

When I finally did, it was something like a step back in time, when hard physical work defined the day. Everyone was busily attending to tasks, some directly with the horses, others doing other ranching jobs. The barnwood was weathered and worn with a floor trumpeting a satisfying clomp under booted feet.

We were greeted by the Wrangler jeans-clad Payne, who efficiently had us sign away any liability for anything that could possibly go wrong. Honestly, that gave me pause just for a split second, especially when I checked the box opting not to wear a helmet while thinking about my husband telling me his first riding experience lasted all of two seconds because he got thrown off the horse.

Without us realizing it, Payne sized us up, physically and probably ability too, and paired each of us with an appropriate horse.

The sweet Palamino named Cutter was chosen for me. As I climbed the very convenient steps to get on Cutter’s back, Payne, now also wearing cowboy boots with jingling spurs, gave me a quick tutorial about getting on the horse and then how to get him to do my bidding. When asked if the horses just basically follow each other even if I do nothing, Payne replied, “pretty much.” Even so, it was a bit daunting being on top of an animal that weighs more than half a ton and which, if you think about it, could really do whatever the heck he wants.

My husband, Tim, got Elvis, whose full name is Showtime Elvis, who is something of a celebrity at the ranch, having been on the popular Showtime series “The Affair” (season 1, episode 2). Patrick Keogh, Cate’s husband, was the stunt double in the show. The Showtime part of his name precedes his guest appearance on the television show.

Payne was riding Coal, her favorite horse in the stable, possibly because she senses a kindred spirit in that when Coal first came to the ranch, he lost a lot of confidence in his skills on the trails. Payne worked with him over the years, and now he’s a top trail leader. Painfully shy as a child, being around horses helped Payne gain her own sense of confidence because she quickly learned “you can’t be timid on a horse.”

Once we were all settled on our horses we set out on the trail, one after the other, with Payne riding Coal in the lead. Right off the bat, we were struck by the sheer beauty of the landscape, riding along a ridge overlooking the meadow where the horses are let out every night or graze and play if they have the day off. In the distance you can see more of the old buildings, the pond and plenty of wildlife. Things are a little less interesting, but still lovely once the trail enters the woods.

At about this point, my horse was making his personality known. Cutter definitely likes to walk very closely behind the horse in front of him. Payne pointed out that horses often put their faces near the tails of other horses to swat away flies, but she added that Cutter also does it to assert himself. Flies, it seems, are a constant for the horses, and while they didn’t bother us, the horses were constantly stamping their hooves to rid themselves of the pests.

Each of the horses has a distinct personality. Describing Cutter, Keogh said in an interview later, that, “he’s adorable, so even though he’s one of the smallest in the herd, he’s one of the biggest personalities. He does not have a lot of patience. He wants to do his job very well and nobody bosses him around.” I’ll say.

Along the path there were many puddles and we were instructed to steer the horses to the middle because otherwise they would take a wide berth into the shrub line. A moment of distraction at one of the puddles proved this to be true.

Just as Cutter and I were getting used to one another, during one of our stops to wait for Elvis with my husband aboard to catch up (Elvis it turns out is pretty much always hungry so any opportunity to grab a mouthful of grass was just fine with him), Payne announced we are going to get the horses to trot.

In theory this sounds okay but it’s then that you realize maybe you should have paid more attention to the adjustment of the stirrups on the saddle before heading out. It’s much easier to bear the trotting if you stand up slightly in the saddle so next time I’d definitely raise the stirrups a notch. And if you’ve squeezed a few kids out, a final pee break before heading out is definitely advisable.

The reward after a few trots to speed up the pace — slowed mostly by waiting for Elvis to catch up — was descending a small sandy hill to a beach with Oyster Pond to the right and Block Island Sound to the left, an absolutely spectacular view in every direction.

As if I was not concerned enough that at the beach Cutter was really trying to assert himself, constantly pulling his head down with a jerk, Payne told us that the horses sometimes lie down in the sand to get the flies off. All I could picture was Cutter rolling over with me on his back but Payne assured me that if they get down they get right back up. I am grateful we didn’t have to test her assertion.

The ride on the beach marked the turnaround point on the ride and the route back was slightly shorter and traversed a lot of deep puddles and rocky terrain. At times, watching the horse in front of me slip a bit and feeling the legs of my horse trying to find purchase on the trail caused a blip of fear but all the while Payne watched us all without a bit of concern as she sat askew in her seat. Riding for 90 minutes, turned nearly all the way around in her saddle, made me wonder what Payne’s back is going to be like in 20 years.

Smiling all the way, despite the few moments of uncertainty in the saddle, we made our way back to the corral where we were invited to sidle our horse up to the water trough while the hands got things ready to help us get off.

It came as a bit of a surprise that once off the horse, it was a bit like sea legs after a boat ride. It didn’t take long to reacclimate and walk away from a day whose memory will last a lifetime. Now to put a check mark on that list … and see what’s next.