*Ashland Fourth Fridays in historic downtown Ashland, Virginia*

*Secretariat for Virginia* *modeling marvelous Kentucky Derby hats and styles*

Ashland Fourth Fridays is trading in March showers for May flowers — and a whole lot of Derby flair. After a beloved Secretariat birthday celebration was rained out earlier this spring, downtown Ashland is making up for lost time in a big way. On Friday, May 22, 2026, from 5 to 8 PM, the Center of the Universe transforms into the center of Kentucky Derby excitement — right outside Ashland Town Hall at 121 Thompson Street, Ashland, VA. The event is completely free and family-friendly, making it the perfect springtime outing for neighbors, visitors, and horse racing fans alike.

Taking center stage in the celebration is Secretariat for Virginia, the official partner organization dedicated to honoring the legacy of the legendary Triple Crown champion who called Virginia home. Secretariat for Virginia will host an exclusive merchandise booth at the event — a rare opportunity for fans to take home officially licensed keepsakes celebrating the greatest racehorse of all time. The fun doesn't stop at shopping: Secretariat for Virginia will also award a curated gift basket to the winner of the event's signature Kentucky Derby Hat Contest. Guests are encouraged to arrive in their Derby best — the more fabulous the fascinator, the better the chances of winning.

The evening kicks off in high style with a Racing Parade presented by Ashland Dance Academy, setting an energetic and joyful tone before the main event gets underway. From there, acclaimed local act Blue Guitar takes the Ashland Town Hall Pavilion stage for a free outdoor concert that promises to be the soundtrack of the night. Whether guests are tapping their toes on the lawn or browsing the vendor lineup, live music fills the air from start to finish.

Art, craft, and food vendors will line the sidewalks of Ashland Town Hall, spill into the Town Hall Parking Lot, and stretch along Hanover Avenue — creating a festive open-air marketplace that showcases local artisans, makers, and culinary favorites. Beloved downtown Ashland shops and restaurants will also stay open late for the occasion, giving guests even more reason to linger, explore, and support the small businesses that make this community shine.

Ashland Fourth Fridays is a signature event series produced by the Downtown Ashland Association to celebrate community, local culture, and the irreplaceable spirit of life in Ashland, Virginia — a town that takes immense pride in its identity as the Center of the Universe. May's installment — with its Derby theme, Secretariat connection, live music, and festive vendors — is poised to be one of the most memorable yet.

Ashland Fourth Fridays on May 22nd is free, open to the public, and welcomes guests of all ages. The event takes place rain or shine at 121 Thompson Street, Ashland, VA 23005. Attendees are invited to follow the Downtown Ashland Association on social media for real-time updates, vendor announcements, and Derby-ready inspiration leading up to the big night.

Event At-a-Glance

What: Ashland Fourth Fridays — Derby Edition

When: Friday, May 22, 2026 | 5:00 PM – 8:00 PM

Where: Ashland Town Hall & Downtown Ashland | 121 Thompson Street, Ashland, VA 23005

Admission: Free & open to the public