Derby Days
-
Start
May 1, 2026
10:00 am -
End
May 2, 2026
10:00 pm
Ashland Derby Days Celebration — May 1 & 2!
Get ready for a weekend full of fun, fashion, and festive Derby vibes! Grab your friends, dress to impress, and celebrate Derby style all weekend long!
Run for the Roses Bingo Bash Downtown Shopping Crawl
Friday & Saturday (FREE to play)
Shop, play, and explore for your chance to win $250 in Chamber Dollars!
Visit participating businesses and complete a fun activity in each store to earn a stamp on your Bingo card. It’s a great way to discover and support Ashland’s amazing local retailers!
- Complete a regular Bingo = 1 entry
- Complete a Blackout = 20 entries
Get your Bingo cards at:
**** Ashland Area Chamber of Commerce – May 1, 8am-4pm
****Any of the participating businesses May 1 & 2
Return your completed Bingo card to The Union, 100 Main Street West, where the Winners Circle Soiree is taking place by 5pm on Saturday May 2nd.
Don’t miss the fun—grab your card and start crawling!
Hat’s Off to the Derby — Hat Making Workshops
$25- pre-registration required
Create your own Derby masterpiece:
• Friday, May 1, 6–8pm — at Flourish or The Collective
• Saturday, May 2, 9–11am — at Fabric Life
Purchase tickets for Hat Making:
Hat Contest — Saturday, May 2 at 2pm at the Hooves of Joy Fundraiser at the Neighborly Bar
Be sure to stop in early to register your hat!
The Winner’s Circle Soirée
$35 includes a whole night of fun! pre-registration required
An unforgettable Derby-style evening featuring:
• Watch Party + Fun Games – 4-6:30pm – Sponsored by Norvado
• Dinner – 6:30pm Appetizers along with Herb Chicken, Homemade Mash Potatoes, Sauteed Green Beans catered by Driftwood Catering
• Live Music by Acoustic Relapse – 6:30-9pm
• Cash Bar
• Costume Contest-Dress your Derby best for a chance to win $100!
Groups that purchase 8 Winner Circle Soiree tickets will have a table reserved for them.
Click this link to Purchase tickets for the Soiree!
Tickets can be purchased online or by stopping in or calling our office 715-682-2500.
Lodging Specials available at:
- Cobblestone Inn & Suites $110
- Best Western Hotel Chequamegon 15% off