Derby Day in downtown Ashland: First Friday celebrates a Kentucky tradition on Derby eve

Published 12:47 pm Friday, May 3, 2019

ASHLAND, Ky. — Downtown Ashland celebrates all things Kentucky Derby on the eve of the 145th run for the roses.

First Friday from 5 p.m.- midnight is set for Friday in downtown Ashland and will feature a cruise-in, live music, an outdoor beer garden, extended downtown shopping hours and children’s activities.

The First Friday Cruise-in welcomes all cars, trucks, jeeps and bikes to display their rides and connect with area car enthusiasts. All makes and models are welcome. Dash plaques will be given to the first 50 registrants. Attendees are encouraged to vote for May’s People Choice Award winner, sponsored by NAPA Auto Parts.

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Cars may begin parking at 3 p.m. on Winchester Avenue between 14th and 17th streets. Vehicles may enter and exit the venue via 16th Street and Greenup Avenue. Winchester Avenue will be closed at 14th and 17th streets to ensure pedestrian safety.

Registration is $5 and enters vehicle owners into a nightly door prize drawing.

Children are invited to make their own Derby hat from 5-7 p.m. inside the GetFiddle Custom Shop located at 1549 Winchester Ave. Hats and decorations are provided. Children’s activities are provided free of charge thanks to Marathon Petroleum.

Stick around GetFiddlle Custom Shop at 7 p.m. and enter your DIY Derby Hat creation for the chance to win a $50 Visa gift card. Derby hats must be made by the entering participant. Hats may be made during the event at Getfiddle Custom Shop or made off-site and worn to the competition. All ages are welcome. Three winners will be selected in the following categories: best of show, funniest and most original. There is no fee to enter.

In addition to the Derby Hat Contest, Getfiddle Custom Shop will also feature the talents of E.K. Station at 5 p.m. and David Austen and Baylee Morgan at 6 p.m.

The Camayo Arcade will feature complimentary wine, mimosas and Mint Juleps in honor of the Derby along with a live musical act. Live music TBA.

Children’s inflatables are located on Judd Plaza and 16th Street and are hosted by BC Tool & Party Rental. Inflatable jumping is unlimited during the event and is $5 per child.

For more information regarding First Friday opportunities and activities, contact or visit