WHINE UP THE HILL
- Date
- October 3, 2026
- Location
- 1 Jagni Loop, Park City, KY
- Distance
- Whine up the Hill · Sip n Stroll · Kid's Run
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. 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
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Events
Weather
Typical Conditions
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
79°
Typical Low
54°
Chance of Rain
27%
Based on US Climate Normals data from Mammoth Cave, 6 mi from the venue.
Host City
About Park City, KY
Population
693
as of 2023
Elevation
642 ft
Nearest Airport
BNA
Nashville International Airport · 76 mi
Time Zone
Central Time
From Endurance Grid
A small town race. Lodging near the start could be limited, so book early.
Race Location
Your Next Start Line
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at WHINE UP THE HILL, put it on the calendar, and turn “someday” into a start date.
Coming Up
More Running races near Park City, KY
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Half Marathon · 10K · 5K
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23 miles away
Medal Madness 5K, 10K, & 13.1M at Bowling Green, KY (26)
Half Marathon · 10K · 5K
23 miles away
Eagle 5K, 10K, & 13.1M at Bowling Green, KY (28)
Half Marathon · 10K · 5K
23 miles away
From Endurance Grid
About This Sport
Endurance Grid is here to help you understand the sport, decide if it's the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer's event page.
With running, there's a distance for every fitness level, a community at every start line, and nothing beats the feeling of crossing a finish line you trained for.
Running is an endurance sport that rewards consistency, and showing up every week compounds in ways that will surprise you.
Running
From 5K to marathon, running races are the most accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Frequently Asked Questions (FAQs)
- What is the WHINE UP THE HILL?
- WHINE UP THE HILL is a running race held in Park City, Kentucky on October 3, 2026. It is one of the many endurance events listed on Endurance Grid, a multi-sport endurance event calendar covering running races, triathlons, HYROX, and more endurance sports across the United States. Find more running races near you or explore our sports guides to learn what race day actually feels like.
- When and where is the WHINE UP THE HILL?
- Saturday, October 3, 2026 in Park City, Kentucky at 1 Jagni Loop, Park City, KY. Check the event page for exact start times and wave schedules.
- How do I register for the WHINE UP THE HILL?
- Registration is handled through the event's registration page. Confirm pricing and distances there, and sign up.
WHINE UP THE HILL
Oct 3, 2026