Equestrian Summer in Upperville and Great Meadow

Summer’s coming up quickly here in the Virginia countryside. The last of the fox hunters have gone to ground and it’s time for the rest of the sporting season: from the steeplechase races to polo, to the horse show season taking off, to fresh country fare at our local restaurants and farmers markets (yep, we’ll truck some of that in for y’all).

The Upperville Colt & Horse Show, the country’s oldest, began on Monday. Now in its 161st year, the show runs through Sunday, June 8, and features more than 2,000 horse-and-rider competitions. Set on the beautiful grounds of the historic Salem and Grafton Farms, “under the oaks,” Upperville combines everything from the finest show hunters in the country to Olympic-level jumper riders.

For me, personally, some of the best events are the Ladies Sidesaddle Hunters, where attire, or “turn out,” must be perfect down to the sandwich in the sandwich case (judges have been known to take a bite); the famous Upperville Grand Prix; and the leadline division, where tots on ponies are led by their parents.

A little bit more about that. Leadline is held on Saturday following the sidesaddle. Children ages 1-6 will be dressed in their own twee finery, in full-on adorable mode. The Grand Prix, featuring some of the best horses and riders in the world, is held on Sunday.

My suggestion: make a day of it. Pack up your coolers with some tailgate-style foods and beverages (preferably adult, but don’t overdo it), grab some chairs and sit on the hill to watch the jumpers go. There will also be an antique auto show, a petting zoo, a moon bounce and – the most fun – Jack Russell Terrier Races!

One note about Grand Prix day. While it’s not specified in the program, many people will be in “afternoon attire.” Fancy dresses and large hats are not out of place. So if you’ve got it, wear it.

If you discover that you enjoy watching the horses jump around while you sip a cold one, Great Meadow is bringing back its Twilight Jumper Series this year. Held June 27, July 18 and August 29, all Fridays, this event in The Plains brings out both local and professional talent for a Friday evening with dancing and wine tasting. Great Meadow encourages you to pack a tailgate, but note that nearly every event at Great Meadow is to be free of glass bottles, lest one injure a horse.

Great Meadow’s Twilight Polo Series has also begun, continuing on Saturday nights through September. There is dancing as well as polo, and – with the Aspen Dale Winery at the Barn on hand – everyone will have a great time. Check the Great Meadow website for this year’s themes: from Military Appreciation Night to Pirate Night.

Make sure you pop back to Great Meadow for the rest of their events on the card for the summer, including a Fourth of July celebration and, later that month, the WEG selection trials. (Ever want to see someone play high jump on a horse without a saddle? Now’s your chance.) The Virginia Scottish Games are at the end of August, the Wine Festival is in September and the International Gold Cup Steeplechase in October.

I know I’ve encouraged tailgating, but you don’t always want to do the prep before the weekend. So, my other best suggestion is to enjoy some local food. (And wine. Always wine. Especially Virginia wine.) Breaux Vineyards in Purcellville will hold its 17th annual Cajun Festival and Crawfish Boil on June 14, with live music and lots of treats. Then Morven Park in Leesburg will host a NOVA Summer Brewfest on June 21-22, so you can do one weekend of wine and another of beer, both with live music and vendors.

There are other notable wine tours in the area – a quick Google search will bring up plenty. If you go to (www.virginiawine.org), there is a list by date of events for the entire summer. With at least one, and often many, every weekend, you can cherry-pick (grape-pick?) your own tour.

Upperville’s classic eating stops include Hunter’s Head Tavern – where your dog can dine on the patio, incidentally – and the Blackthorne Inn, with its beautiful bar. Another of my personal favorites is The French Hound in Middleburg, where the menu changes in accordance with the “whims of the chef.”