The hour-long trail ride led by Rocking S. Ranch owner Bill Schwasta (in cowboy hat) passes Oak Hill, a former residence of Supreme Court Chief Justice John Marshall. (Kris Coronado/PHOTO BY KRIS CORONADO)

The cowboy boots were probably not a good idea.

Thinking that the used snakeskin kicks I picked up on a spring jaunt to Austin deserve some authentic strapped-in-the-stirrup action, I proudly stride up to Bill Schwasta as he leads a quartet of horseback riders in from a gravelly trail.

Details: How to get to Barrel Oak Winery, where to stay and what to do

“You must be Miss Kris,” he says from atop his quarter horse, Trooper. He has just finished an hour-long ride through the hills and forest of the 170 acres of Barrel Oak Winery in Delaplane, Va. Since mid-July, Schwasta has been driving 40 miles from his Rocking S. Ranch in Winchester to run what he calls “Alfresco Saturdays” at Barrel Oak. Fifty-five dollars gets visitors astride one of the six horses that he has temporarily settled beneath a leafy tree near the winery’s entrance.

Dismounting, Steve and Donna Sydorak of Lehigh Valley, Pa., are bursting with how much they’ve enjoyed the last 60 minutes. “We felt safe the whole time,” says Steve. “The landscape was beautiful. Outstanding.”

Their enthusiasm is catching, and I’m eager to experience the ride for myself. Perhaps a little too eager. It seems that my footwear and a Jackson Hole, Wyo., T-shirt give Schwasta — who looks like Buffalo Bill with his Stetson-style hat and long white mustache — the impression that I may actually know what I’m doing. “Kris, you’ve done this before,” he says. “You’re a pretty good rider, right?”

I can’t stop myself from cockily answering, “Oh, yeah, sure. I’d say I’m an intermediate. Well, a pretty good beginner.” Apparently the two or three other times I’d gone on novice horseback excursions has now made me akin to Calvin Borel.

It’s a feeling that persists as I sit atop my 13-year-old mount, Dallas. Before we head out, Schwasta warns me not to let Dallas “get the drop” on me by dipping his head to munch weeds and grass. If the horse starts to make a move for the greenery, a quick and assertive yank of the reins should do the trick. A few minutes after my friend Leigh has settled on her horse, Moonlight, he does just that. I’m giggling at her failed attempts to bring her misbehaving mount’s head back up, and cheering her on encouragingly. Because this will never happen to me, of course.

The ride begins at a slow pace over a dirt Colonial roadway recently uncovered by the winery’s founder, Brian Roeder. Here, Schwasta gets chuckles from his group of riders — Leigh and I are accompanied by some teens from Wayne, N.J., and Schwasta’s 14-year-old daughter, Shane — by offering up heinously bad jokes. What did the fish say when he ran into the concrete wall? Dam!

We amble, and at times trot, to a dilapidated yet elegant white mansion named Oak Hill, an early residence of chief justice of the United States John Marshall. Riding around this property and an abandoned farmhouse makes you feel as if time’s clock has rewound. You almost expect to catch sight of someone in 19th-century attire around the corner.

The wind blows gently, and the pace is leisurely as we cross a small dry creek bed. The ride begins to feel less foreign, more second nature.

That’s when Dallas makes his move.

With a quick jerk of his head and a rustle of leaves, he suddenly has a massive pile of brush between his teeth. I yank on the reins, but there’s no stopping this chomping. The rest of the group, which has progressed into the woods, halts. This is where Schwasta had planned to check our gear, and the timing couldn’t be better: Dallas is no longer responding to my pleas to budge.

Calvin who?

With some help from Schwasta, I’m able to get going again. But my bravado is gone, replaced by a slight knot in my stomach. I start wondering whether I should have worn a helmet, like the ones required for the teens.

These misgivings, however, melt away when we emerge onto a grassy knoll speckled with wild flowers and offering a breathtaking view of the two Cobbler mountains in the distance. It starts to rain as we approach the vineyard, but my spirits aren’t dampened. The downpour feels downright magical.

After I not-so-gracefully dismount from Dallas, Leigh and I head to Barrel Oak’s outdoor tasting bar. The rain has let up, and the sommeliers are setting up again, allowing us to walk right up to this usually packed spot.

Behind the counter, Matt Boyd takes us on another journey, albeit a tamer one. We opt for a half-tasting of six wines.

For the next half-hour, we sip a buttery Viognier, a crisp Seyval blanc and a peppery cabernet franc. Each of the seven wines (the cab was a bonus pour from Boyd) gets our approval. Admittedly, the libations taste that much better when you know that you’ve successfully managed to remain upright on a horse. Sweet relief never tasted so good.

Details: How to get to Barrel Oak Winery, where to stay and what to do

Coronado is a freelance writer in Arlington. Her Web site is

L’Auberge Provencale

13630 Lord Fairfax Hwy. Boyce, Va.



French-style country inn with Zagat-rated restaurant. Rooms from $170, including gourmet breakfast.

Goodstone Inn and Estate

36205 Snake Hill Rd. Middleburg


Luxury inn situated on 265 rolling acres. Rooms from $265.

Iron Bridge Wine Co.

29 Main St.



Wine bar that pairs eclectic small plates with a variety of vintages. Three courses for $35. Open Sunday through Wednesday.

Apartment 2g

206 S. Royal Ave.
Front Royal


Watch chefs prepare your meal via live feed in this apartment-style space. Five-course prix fixe ($50) on Saturday evenings. Reservations required.

Barrel Oak Winery

3623 Grove Lane Delaplane


Hour-long horse rides from 11 a.m. to 5:45 p.m. Saturdays through November (weather dependent). $55 per person. Reservations may be made in advance or on-site.

Tasting fee $6 for six wines, $10 for 12. Fees waived with purchase of a case.