WHINE UP THE HILL

About the Event

"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 Life Choice Pregnancy Center, supporting their incredible work in our community including free Pregnancy testing, Limited Obstetric Ultrasound, Options Information, Parenting Classes, Baby items including diapers and so much more!".

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 Life Choice Pregnancy Center of Franklin KY
Features: Challenging hill (2.24mi course), vineyard route, wine tasting (21+), beautiful scenery
Follow Us: Follow us on Facebook

Races Offered

Oct 03, 2026

straighten

Distance — 2.24 Miles

terrain

Type — Running

timer

16:00

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$30.00

Sip n Stroll

Oct 03, 2026

straighten

Distance — 2.24 Miles

terrain

Type — Running

timer

16:05

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$30.00

Kid's Run

Oct 03, 2026

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Distance — Kids Run

terrain

Type — Running

timer

16:10

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$15.00

Weather History

These values represent the 3-year monthly averages for October in Park City.

thermostat Temperature

11.0° / 21.8°

wb_sunny Feels like

8.8° / 20.0°

light_mode Avg sunshine hours

9h 0m

water_drop Avg rainfall

2.5 mm

ac_unit Avg snowfall

—

air Avg wind speed

10.3 km/h (Light breeze)

opacity Sweat loss rate

Moderate

terrain Course conditions

Firm and slightly soft

sunny Max UV Index

Moderate (4.0)

humidity_mid Humidity

69.5%

wb_twilight Sunrise

06:53

nightlight Sunset

18:06

About Park City

Learn more about the host city, Park City.

Park City is a home rule-class city in Barren County, Kentucky, United States. The population was 614 at the 2020 census. It is the entrance to nearby Mammoth Cave National Park and to Diamond Caverns, a privately owned cave attraction. Exit 48 off I-65 is the only direct access exit to the Mammoth Cave National Park.