There are plenty of flashy ways to travel from winery to winery in the Willamette Valley. Stretch limos can help you revisit the glam of high school prom. A party bus screams, "I don't care about vintage years and lot numbers, just get me drunk!" You can even rent a helicopter that uses the countryside as its landing pad.

Equestrian Wine Tours (6325 NE Abbey Road, Carlton, 503-864-2336equestrianwinetours.com) offers a humbler option. But while touring Oregon wine country by horse takes a little more grit, the reward is a walkable lesson about the land and wildlife that normally only the vineyard workers get to experience.

(Christine Dong)
(Christine Dong)

"People have to have a little spirit in them to do this kind of thing," says guide Sarah Ann Hahn, whom I meet at a corral on the edge of a wide meadow at Winter's Hill Estate in Dayton.

I quickly learn what she means. Because before you can drink, you must learn how to ride.

My horse is actually as docile and sweet as a well-trained dog. Chipper, a 15-year-old Tennessee walker who used to compete in exhibitions, is enjoying what could be described as a more laid-back second career carrying around tourists. Still, the thought of leading this small mountain of muscle was a bit intimidating.

But Hahn—waiting astride her own horse, Kahlua, and dressed in a plaid pink button-down and loose scarf matching the splashes of pink paisley print on her cowboy boots—breaks it down pretty simply. She slides a stool next to Chipper's side and directs me to stick my left foot in the stirrup, step up and use that momentum to fling my right leg across his back. With one somewhat hesitant thrust, I am up—sitting 6 feet off the ground.

Hahn has assumed much of the responsibilities at Equestrian Wine Tours from founder Jake Price, who started the company 10 years ago. Age and health have slowed him down a bit, so Hahn has taken on the task of filling his saddle and leading field trips through a handful of Dayton vineyards, which are booked almost every day of the week during summer. Her familiarity with the environment gives her almost as much insight about the grapes as the farmers.

"Like a farmer, you know and see your crop," she explains while traveling between wineries. "You get to see the vineyard and know when bud break happens, and know if it'll be an early year or a late year."

Traveling along a dirt path next to perfectly aligned rows of now-bare trellises, I notice how fluid my horse feels—no jerking up and down like a paddle ball as he takes steps. It's a mark of the breed, I'm told. Tennessee walkers are apparently known as the Cadillac of the horse world.

I soon spot the horse parking as we approach the back side of Vista Hills Vineyard & Winery (6475 NE Hilltop Lane, Dayton, 503-864-3200vistahillsvineyard.com), which wouldn't be out of place among the million-dollar homes in Portland's West Hills with its wall of oversized windows, soaring ceilings and modern lines.

(Christine Dong)
(Christine Dong)

Hahn and I leave our horses to be ogled by visitors who arrived in their boring old cars and head to the second-story tasting room. While the interior is striking, with honey-colored beams and a large stone fireplace, take your Treehouse Flight—four tastings are normally $20, but that's cut in half for Equestrian Wine Tour participants—to the sprawling deck. At more than 800 feet in elevation, you'll have a view of acres of grape plants unfolding in front of you, and can wave at your horse while sipping an earthy pinot noir.

On the way to the second winery, we duck into a forest dominated by alder and blackberry bushes before pushing out into a field that used to be a filbert orchard. Since we're on a flatter surface, Hahn suggests trying a little run-walk. I didn't even need to prompt Chipper. As soon as Kahlua gets going, he springs into the next gear. It's like riding one of those little traveling carnival roller coasters where the quick burst of acceleration makes your stomach spring.

I learn that Hahn has much more experience with stunts that put my thrill-seeking trot to shame. She's a trick rider with the Riata Ranch Cowboy Girls, a traveling performance group with which she vaults over her horse, stands on its back and has even mastered a one-legged, upside-down move called the suicide drag. At some point, you may be able to watch one of these Wild West-style shows at area wineries: It's her dream to find new ways to share her passion for horses with vineyard visitors—some of whom she discovers have never seen a horse in person.

We tie up at what appears to be a small home just outside White Rose Estate (6250 NE Hilltop Lane, Dayton, 503-864-2328, whiteroseestate.com) and then walk down a long driveway. It looks like a hobbit's version of a French chalet. The gray wooden building is sunk into a hill and has no windows, but manages to exude coziness in an almost clubby atmosphere. When possible, ask to traverse farther below ground where there's a second hidden tasting area and castle-style doors leading to the barrel room. There you'll find a split-wood, ratchet-style basket press that actually works. Much of White Rose's equipment is crafted at Ponderosa Forge & Ironworks in Sisters, Ore., because, as owner Greg Sanders puts it, "we're allergic to plastic."

It's interesting how many people at the wineries remark about how much safer our mode of transportation is while out tasting. But it's not impossible to get busted while drunk on a horse. Laws vary by county, but one law firm says prosecutors could attempt to move forward with a variety of charges if they see fit, including riding while intoxicated, drunk in public or cruelty to an animal. As an added safety measure, the guides at Equestrian won't hesitate to pull a rider who's showing signs of impairment or failing to follow directions, and only tasting flights are allowed during the tour—no full pours.

Our leisurely pace means downing the rest of my flight ($20 for four samples) quickly in order to complete our circuit at Winter's Hill (6451 NE Hilltop Lane, Dayton, 503-864-4592, wintershillwine.com). Admittedly, I'm a bit buzzed as we start down a gravel road, but I'm certain Chipper could operate on autopilot if he had to.

After crossing another field and weaving through more vineyard land, we're back at the corral. A pair of coyotes amble off in the distance—they're regulars, Hahn says. Inside, you feel as if you're drinking behind the scenes. Flights of five cost $15, and there are few frills, but you're surrounded by pallets of bottles, shiny silver tanks and a press that looks like a space shuttle.

It's a little after 5 pm, but Winter's Hill accommodates Hahn's tour by letting us stay a bit past closing time. I say goodbye to Chipper, who's headed home to his farm about 12 minutes away, and tell him I hope I was a decent partner to have on his back for an afternoon. By the end of the two-and-a-half-hour journey, it's easy to become convinced you could lead a cattle drive through the rolling hills of Yamhill County. Though that might just be the pinot talking.