WHINE UP THE HILL

Sat, Oct 3, 2026, 4:10 PM CDT

Location: Park City, KY; 1 Jagni Loop, 42160
Type: RUN

At a glance

Conquer a challenging hill, enjoy scenic vineyard views, and savor local wine tastings, all while supporting a great cause.

Fun
Scenic
Competitive
Quirky
For a Cause

Great for

Beginner Friendly
For a Cause
Family Friendly
Walkers Welcome

Great for: beginners, walkers

Embrace a unique challenge at the Whine up the Hill, set at the stunning Maple Retreat near Mammoth Cave National Park. This event offers a distinctive course featuring a steep climb, rewarding runners and walkers with scenic vineyard views and local wine tastings (for those 21+). Choose from a timed run/walk, a leisurely Sip-n-Stroll, or a fun Kid's Run. Beyond the unique experience, your participation supports a local nonprofit in Southern Kentucky, making every step meaningful.

What to expect

Tackle a unique, hilly course winding through a beautiful vineyard.Enjoy wine tastings from local wineries (21+) along the route.Choose from a timed run/walk, a leisurely Sip-n-Stroll, or a Kid's Run.

Standout details

Challenging hill climb
Scenic vineyard course
Local wine tastings (21+)
Benefits a local nonprofit

Perks & features

Shirt

From the public listing — confirm on the official site.

Auto-drafted from the public listing — confirm details on the official event page before signing up.

Distances & registration

3 options

Registration for all distances is through the official signup link above.

2.24 Miles
Sat, Oct 3, 4:00 PM CDT · From $32.80
Opens Mar 11, 2026, 8:00 PM CDT · Closes Jun 30, 2026, 7:59 PM CDT
2.24 Miles
Sat, Oct 3, 4:05 PM CDT · From $32.80
Opens Mar 11, 2026, 8:00 PM CDT · Closes Jun 30, 2026, 7:59 PM CDT
Kid's Run
Sat, Oct 3, 4:10 PM CDT · From $16.90
Opens Mar 11, 2026, 8:00 PM CDT · Closes Oct 3, 2026, 11:00 AM CDT

The course

Hilly
Walkers welcome

From the organizer

"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 Follow Us: Follow us on Facebook

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