Middleburg’s Spring Social Scene
By • April 14, 2026 0 1209
Just like Washington, D.C., Middleburg, Virginia — recognized as the country’s horse and hunt capital — has a packed spring social scene. Grab a mint julep and your finest hat and head to these glamorous gatherings.
Saturday, April 18
Middleburg Spring Races
Scheduled for Saturday, April 18, at Glenwood Park, the Middleburg Spring Races mark the sanctioned kickoff to Virginia’s spring steeplechase season. Often called a “quintessential rite of spring,” the event is famed for its picturesque setting, where the blooming dogwoods and daffodils frame some of the country’s most competitive jump racing.
Sunday, April 26
Middleburg Hunt Point-to-Point Races
Also at Glenwood Park, the Middleburg Hunt Point-to-Point Races will take place on Sunday, April 26. Considered a more relaxed and community-focused precursor to the sanctioned spring races, this event features a mix of timber and brush races in which amateur and professional riders compete over the rolling hills of Virginia’s hunt country.
Saturday, May 2
Virginia Gold Cup
The 101st running of the Virginia Gold Cup is scheduled for Saturday, May 2, at Great Meadow in The Plains. “Virginia’s answer to the Kentucky Derby,” this prestigious steeplechase event draws over 30,000 spectators for a day of world-class racing, set against the backdrop of the Blue Ridge Mountains.
Saturday, May 9
Art in the Burg
Art in the Burg, on Saturday, May 9, from 11 a.m. to 6 p.m., transforms Middleburg’s South Madison and Federal Streets into a vibrant pedestrian gallery. The annual open-air arts festival features more than 30 local and regional artists and artisans.
Saturday, May 16, and Sunday, May 17
Boxwood Estate Winery Spring Socials
The Boxwood Estate Winery Spring Socials on Saturday, May 16, and Sunday, May 17, are exclusive, members-only events designed around the season’s wine allocation. Held at the Middleburg winery’s sleek, modern estate, the weekend serves as a “pickup party,” with club members collecting their spring packages while enjoying a sophisticated social atmosphere.
Monday, June 1 through Sunday, June 7
Courtesy Upperville Colt & Horse Show.
173rd Upperville Colt & Horse Show
The 173rd Upperville Colt & Horse Show will take place from Monday, June 1, to Sunday, June 7. The oldest horse show in America, it remains a cornerstone of Virginia’s horse country, held under the historic oaks of Grafton Farm and Salem Farm Showgrounds.
Where to stay and eat:
Looking for a place to stay or eat as you head to the Gold Cup or Upperville Colt and Horse Show? The recently opened Hotel Burg is a great option. Its elegance, sophistication and intimate vibe are perfect for travelers headed to Middleburg for the town’s vibrant spring social scene. The Hunton Restaurant at the Hotel Burg includes a menu inspired by bounties of the hunt. While it’s open to the public, reservations are recommended. The Diana Lounge at The Hotel Burg offers breakfast, lunch, dinner and cocktails and is open to the public with walk-ins welcome.
The patio at Hotel Burg. Courtesy Instagram/hotelburgva.
Also, beginning April 22, The Rooftop at Hotel Burg will be open to the public on Wednesdays from 4 to 10 p.m. and every first Friday of the month from 4 to 11 p.m. Previously, except for Wednesdays, it had been reserved for members of the private social club The Chase only.
