Horseflies, the size of winged pigs-in-a-blanket, buzz around Sundance’s haunches looking for an appetizing spot to land. The dapple-gray quarter horse stomps her hind legs and whisks her tail in retaliation, her skin twitching irritably beneath the saddle. While she does her best to keep the flying vampires at bay, I loosen the reins to allow her access to the grass below and look out over the marshlands of Cherry Bridge Creek. A steady, pre-thunderstorm breeze wrinkles the muddy face of the water and forces the cattails to collide and clap under an overcast sky. “This is where I come when I need to get away,” says our trail riding guide, Caroline Rider, owner of Caroline Rider Natural Horsemanship. “I bring a book and chill out. I love this spot.”

And it’s easy to see why. There’s only one thing better than being on the water and that’s riding alongside the water. And what’s neat about this trail ride is that it’s a truly well-rounded Chesapeake experience: You get to see a combo of water, marshes, and farms, wide-open landscapes and sheltered, forested areas.

It’s nearly ninety degrees on this mid-September afternoon, and we’re not the only ones feeling the heat. Rider’s yellow lab, Sidney, slips down the creek bank into the shallows for a dip and busies herself digging in the silty bottom. All that’s missing from this picture-perfect scene is a picnic basket loaded with fried chicken, a blanket to sprawl out on under the oak tree—and a bottle of DEET. And since the flies (Rider calls them B-52s), are beginning to turn their hungry attentions to us, we decide to break camp.

As we tromp through the fields, evidence of summer’s drought is all around us. Beneath our horses’ feet, corn stalks, brittle and tan, snap and crunch. We follow the field along the creek’s edge until the towering grasses obstruct the water view. It seems that the heat is causing the wildlife to play possum; we don’t see as much as a turkey vulture stirring. And maybe that’s a good thing since I’m not entirely convinced that the third member of our party, photographer Kirsten Beckerman, is going to make it through this assignment. Having never been on a horse before, it’s clear that this is not her idea of a relaxing time. “Can horses tell when you’re nervous?” she timidly asks Rider.

“Do you really want her to answer that?” I respond with a chuckle, noticing her hands locked in a death grip around her saddle’s horn. 

There’s one thing you don’t have to worry about when women gather and that’s a lack of conversation. Rider keeps the chitchat moving at a steady clip, explaining that she has been riding since age four. It was her passion for horses that brought her and her husband, Eric (they’re both Salisbury University grads), back to Maryland after a stint running a graphic deign company. In 2004 they bought a sixteen-acre farm, Rider’s Crossing, in Whitehaven on which they built a riding arena and barns and filled them with all manner of rescued creatures: Polish roosters, cats, Chincoteague ponies. “I vowed that I’d never come back to the Shore,” says Rider, sporting a “Cowgirls Rule” ball cap. “But it was important for me to return to a place that represented a lot of peace and tranquility so that I could be centered.”

Rider began offering trail rides at the farm two years ago. Folks can either bring their own horse or rent one of Rider’s to take through the nearby fields or Pemberton Park, Assateague State Park, Tuckahoe State Park, Idylwild Wildlife Management Area, or Wye Island Natural Resources Management Area. Those wishing to stay overnight can rent a stall for their horse at the farm and reserve their own lodging at the nearby Whitehaven Hotel (410-873-2000; whitehaven.

tripod.com). In addition to trail rides, she also teaches private and group lessons for dressage, barrel racing, and three-day eventing. But her real passion is training problem horses through natural horsemanship. Yep, she’s also a horse whisperer.

Once safely back at the barn, with the horses untacked, Rider gives us a demonstration of her training methods, using Smokey and Legend as her pupils, whom, she explains, weren’t always so docile. When she first bought Smokey, he had been through six owners in five years and abused along the way. At times catatonic from the trauma, he would buck, bolt with a rider on his back, and everything scared him. And for three years, Legend had been turned out to pasture without much human contact. As a result, he also bucked, reared, and bit like a champ. “No one wanted them,” she recalls matter of factly. “But I felt a connection to them.”

Grabbing a carrot stick, an eight-foot-long baton-like training tool, she opens the gate leading from the barn to the riding ring. “Come here,” she energetically calls the two horses.

With the eagerness of two Labradors, they follow. Using only subtle body movements, facial expressions, and hand signals, she “asks” them to do a multitude of movements, from leaping over barrels at a standing jump to side passing to cantering in tight circles. After each exercise, the horse approaches Rider and nuzzles her, seeking praise and affirmation. “The way I see it,” she says, “I feel from them a level of wanting to be accepted and to join up with me. They want to please me.”

In the past two years, Rider, who has seven horses of her own, has trained some 200, breaking them of bad habits and even worse attitudes. Once the horses are trained, she then hosts day-, weekend-, and week-long training clinics to teach riders how to handle and connect with their newly reformed horse. “It’s all about relationship,” she says. “It’s very spiritual and soulful to have that kind of connection.” 

We give a final pat to Legend and Sundance, promising Rider that we’ll take her up on her kind offer to hit the trails again with her before winter arrives. Next time, Beckerman tells me as we drive down the farm’s gravel lane, she’ll make sure she learns some breathing techniques to help her cope with the nervousness. And I vow to loose a few pounds so I can fit into my Wrangler jeans once again. But as for the setting and our horses, we wouldn’t change a thing: wide-open spaces and trusty steeds. What more could a cowgirl ask for?

Caroline Rider Natural Horsemanship, 2764 Whitehaven Rd., Whitehaven, Md. 410-873-2350, carolinerider.com. Trail rides range from $135 to $350. All-day rides include lunch and transportation from Rider’s farm to the riding destination.