WHINE UP THE HILL

"At least it's not a 5K"

Get Ready to Whine (and Wine!) at the 2nd Annual Whine up the Hill!

Tired of the same old events that are always a 5K? Ready for a challenge with a delicious reward? Mark your calendars for Saturday, October 3rd, 2026, and join us at the stunning Maple Retreat in Park City, Kentucky (near Mammoth Cave National Park) for the first-ever Whine up the Hill!

This isn't your average race! Prepare to conquer our signature challenge – a steep climb that might just make you "whine" a little! But trust us, the view (and the vino) from the top is worth it. Our unique course, slightly shorter than a traditional 5K, takes you up the hill and then rewards you with a scenic journey through the vineyard.

Along the way, local wineries will be waiting with tasting tables, ready to offer you a sample of their finest creations (for participants 21+ with ID, of course!).

A distance for all levels:

Whine up the Hill Run/Walk (Timed, Competitive Event): Tackle the hill, soak in the vineyard views, and enjoy the wine stops. Perfect for runners and walkers seeking a fun challenge. Participants will receive a long-sleeve shirt, while those age 21+ will also receive a commemorative wine glass. Photo ID will be required at packet pickup

Sip-n-Stroll: (Non-Timed Walking Event) Would you rather enjoy the scenery with a little less "whine" and head straight for the wine? This leisurely walking option is on the same course as the competitive event but lets you enjoy the beautiful vineyard scenery and tasting stations at a relaxed pace. Participants will receive a long-sleeve shirt, while those age 21+ will also receive a commemorative wine glass. Photo ID will be required at packet pickup

Grape Gallop Kid's Run: A fun dash for younger runners! Let them burn off some energy in a safe, shorter course that runs in a looping course around the hilltop. This event is open to participants aged 6-12 years old. participants will receive a shirt and finishers medal. 

More Than Just a Race:

Feel great knowing that all proceeds benefit a nonprofit in the Southern Kentucky region. More details coming soon.

 

Ready to whine, wine, and walk/run for a great cause?

Details:

What: Whine up the Hill Run/Walk, Sip-n-Stroll, Kid's Run
When: Saturday, October 3rd, 2026 4:00 PM - Packet Pickup Before Race 3:30-3:55pm
Where: The Maple Retreat, 1 Jagni Loop Park City, KY
Why: Benefit a local nonprofit
Features: Challenging hill (2.24mi course), vineyard route, wine tasting (21+), beautiful scenery
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