WHINE UP THE HILL
About this race
"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. This year, the proceeds from the event will benefit Life Choice Pregnancy Care Center of Franklin KY. Life Choice provides free and confidential services including: Pregnancy Testing, Pregnancy Confirmation, Limited Obstetric Ultrasound, Parenting Classes, Baby Items, and Pregnancy Options Coaching.
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 Life Choice Pregnancy Care Center
Features: Challenging hill (2.24mi course), vineyard route, wine tasting (21+), beautiful scenery
Follow Us: Follow us on Facebook
Pick your distance
Running
Whine up the Hill
Whine up the Hill Run/Walk (Competitive, Timed Event): Tackle the hill, soak in the vineyard views, and enjoy the wine stops. Perfect for runners and walkers seeking a fun challenge. Awards will be given to top 3 overall male and female winners Awards will be given to division winners in 10 year age increments. Participants over the age of 21 years old will receive a commemorative wine glass Photo ID will be required at packet pickup
Walking
Sip n Stroll
Sip-n-Stroll: 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. The Sip n Stroll is a non-competitive event. Take your time and enjoy the wine. There are no awards for this event. Participants over the age of 21 years old will receive a commemorative wine glass Photo ID will be required at packet pickup
Typical race-day weather
Based on 1 year of Open-Meteo archive data for this event's race dates in Park City, plus the 3 days either side.
The sun rises at 6:41 AM and sets at 6:24 PM local time (CDT) in Park City on October 3, 2026 — 11h 43m of daylight.
Course
No course map published yet.
The organizer hasn't released a route for this event, and we don't publish guesses. If you're the organizer, send us a GPX file and we'll draw the profile.
Reviews
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2026 results — WHINE UP THE HILL
Whine up the Hill · 15 finishers
| Place | Name | Time | Pace |
|---|---|---|---|
| 1 | Janice Lockwood | 20:24 | 9:06 /mi |
| 2 | Heather Wilson | 21:22 | 9:32 /mi |
| 3 | Christina Banville | 22:40 | 10:07 /mi |
| 4 | April Shaw | 30:23 | 13:34 /mi |
| 5 | Pamela Wilson | 32:26 | 14:29 /mi |
Every finisher is on the results page, filterable by distance, gender and age group.
All results by year
Other races near Park City
Different organizers, within 40 miles, in the next three months
Mammoth Cave 50K/25K
FROZEN 4 Mile Run & 2 Mile Walk
The 40th Annual Great Turkey 5K Run & Gobbler Walk
bg26.2 & half marathon and bg6000
Where this page comes from. Race details were last updated on . We re-check listings regularly and again in the week before race day.
- Entries, prices, waves and inclusions — the event's official registration page
- Temperature and humidity — Copernicus ERA5 reanalysis via Open-Meteo (CC BY 4.0)
- Elevation and terrain relief — Copernicus DEM GLO-90, ESA (CC BY 4.0)
- Comparisons and counts — Race Discovery calendar, 2 Park City events
Spotted something wrong? Tell us and we'll fix it.