The Two Octobers of The Plains

A town of two hundred and forty-five people does not usually host one of the largest steeplechase meets in the country. It also does not usually run a 79-year-old art fundraiser out of a parish hall on Main Street. The Plains does both, three weeks apart, every October, without either one crowding out the other.

The trick isn't scheduling. It's geography. The two events happen in the same month but not in the same place, and understanding why tells you more about how this town actually works than any single festival could.

A Church Hall Sized to the Town

The Piedmont Regional Art Show & Sale opens its 79th year this October, running October 2 through 4 at Grace Episcopal Church at 6507 Main Street. It started in 1947 when the Reverend H.B.W. Peters, then rector of Grace, paired with local artist Barbara Middleton to hang a show of neighborhood work as a church fundraiser. Aside from a pandemic-forced skip in 2020, it has run every year since, which is why a show that started the year Jackie Robinson broke into the major leagues is only now reaching its 79th running rather than its 80th.

The show still fits the town it was built for. Artists can enter up to three pieces. A panel of three judges evaluates the work. Sale proceeds are split between the artist and Grace's ministries. Admission to view the art is free. A sponsors' and artists' preview runs the Friday evening before the doors open to the public, the kind of small, unhurried gathering that a volunteer-run parish show can manage and a stadium-scale event cannot.

This year the show shares its opening weekend with Day in The Plains, the town's own celebration held Saturday, October 3, which means the same few blocks of Main Street carry both the gallery crowd and the town-wide event at once. It is, in scale, an event built for a town of 245.

A National Fixture That Moved In

Three weeks later, on October 24, the 89th International Gold Cup runs at Great Meadow, the 374-acre nonprofit field events center on Old Tavern Road. The race itself is older than the town's relationship to it. It began in Tennessee in 1930 and relocated to Virginia in 1984, and it now draws jump-racing competitors from the United Kingdom, Ireland, and France to run alongside the American field. Where the art show is homegrown, this is an import that found its permanent address here.

The card is built around the International Gold Cup timber stakes, a roughly three-and-a-half-mile test over solid post-and-rail fences, paired with the Grade 2 David L. "Zeke" Ferguson Memorial hurdle stakes at about two and one-eighth miles. Around those two features sit maiden, allowance, and handicap races, typically eight in total, plus the tailgate contests, hat contests, terrier races, and Jack Russell parades that have become as much a fixture of the day as the racing itself.

None of that comes free, and the ticket structure tells you something about who this event is built for. A single Members Hill admission runs $81, with a Pavilion Experience upgrade at $189. Parking on the North or South Rail is a separate $108, or $10.80 for a rideshare pass if you'd rather skip the lot entirely. Rail tailgate spots scale from a two-person setup with reserved parking at $270 up to a 75-person chalet package with 25 parking spaces for $3,888. It is, in every dimension, an event sized for a regional and out-of-state audience, not a parish hall crowd.

Two Events, One Road, Different Ends of It

Old Tavern Road is the connective thread and also the reason the two events never actually compete for the same physical space. Great Meadow's address puts it out along that road, past the edge of the town's own compact limits, which cover a total of three-tenths of a square mile. The art show happens inside that same three-tenths of a square mile, on Main Street, walkable from anywhere in town. The Gold Cup happens outside it, on a fairground-scaled property built to absorb a crowd many times the size of the town's population.

That separation shows up in the smallest, most practical details. Gold Cup race-day directions instruct drivers approaching from the north and west not to use the Plains exit off I-66 at all, because access to several gates will be closed off by police that day. It's a genuinely useful thing to know if you live here and have somewhere else to be on October 24: your own highway exit becomes, for one Saturday, a race-day gate rather than a way into town. The art show three weeks earlier asks nothing like that of the road network, because it was never built to move that much traffic in the first place.

The two events also carry two different kinds of judging. At Grace, three volunteer judges pick a Best in Show from among the pieces entered by local painters working in oil, watercolor, and colored pencil, subjects ranging from portraits to farm animals to the surrounding landscape itself. At Great Meadow, judging happens over a timber course against a clock, with an international field and pari-mutuel wagering attached to the outcome. Both are real contests. Neither one is a smaller version of the other. They're built for entirely different audiences, and the town accommodates both by keeping them in their own separate corners of the map.

What doesn't change is the town itself in between. The same Main Street that hosts the art show and Day in The Plains in early October is still there, still walkable, still the same few blocks, on the Saturday morning three weeks later when thousands of cars are being routed around it toward a racecourse most of those visitors will never see the inside of the village from at all.

If you're weighing what it actually feels like to live somewhere that holds both a parish fundraiser and a national steeplechase meet on its own calendar, that's exactly the kind of on-the-ground read Brett Molenaar is glad to talk through, whether you're headed to the church hall, the rail, or just trying to figure out which Saturday to avoid Exit 31.