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This Weekend in Virginia Horse Country (October 23–25, 2026)

Two polo players on horseback contest the ball at Roseland Polo, King Family Vineyards in Crozet, as spectators watch from a picnic blanket with the Blue Ridge Mountains behind.

Fall is in full swing across the Commonwealth, and this weekend brings one of Virginia's marquee steeplechase days alongside polo, eventing, and a horse show with a Halloween twist.

The biggest draw is the International Gold Cup Steeplechase on Saturday at Great Meadow in The Plains — one of the oldest and most prestigious jump race meets in the country, with a full card of racing plus tailgating on the hill.

Down in Lexington, the Virginia Horse Center Fall Classic wraps up its multi-day run at the Virginia Horse Center through Sunday, drawing hunter/jumper riders from across the region for the final rounds.

If you're near Charlottesville on Sunday, head to King Family Vineyards for the Roseland Polo Sunday Match — chukkers on the lawn with the Blue Ridge as a backdrop, a laid-back way to close out the weekend.

Costumes are welcome at the Oakdale Halloween HT, CT & Dressage Show on Sunday at Oakdale Equestrian Center in Powhatan, where eventing and dressage riders will be dressing up their horses as much as themselves.

And in Williamsburg, the Williamsburg Therapeutic Riding Show at Dream Catchers at the Cori Sikich Therapeutic Riding Center celebrates riders of all abilities — well worth a visit if you're in Tidewater.

Looking ahead

The calendar doesn't let up after this weekend. Mark your planner for:

Check each event's page for start times, tickets, and parking details — fall weather in Virginia can turn fast, so bring layers.

Photo: Roseland Polo, King Family Vineyards, Crozet.

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