WHINE UP THE HILL
- Date Sat 3rd October 2026
- Time 4:00PM CDT
- Location Park City, Kentucky
- Price $16.90 - $32.80
- Races 3 races
Event summary
Get ready for a unique and exhilarating experience at the 2nd Annual Whine Up The Hill event, taking place on Saturday, October 3rd, 2026, at the picturesque Maple Retreat in Park City, Kentucky! This exciting event is not your typical race, as it features a challenging 2.24-mile course that takes participants on a steep climb, rewarding them with breathtaking views and delightful wine tastings along the way.
Whether you're looking to tackle the hill in the competitive Whine Up the Hill Run/Walk or prefer a leisurely pace in the Sip-n-Stroll, there's something for everyone. Plus, kids aged 6-12 can join in the fun with the Grape Gallop Kid's Run! Enjoy complimentary long-sleeve shirts and, for those 21 and older, a commemorative wine glass awaits at the finish line. All proceeds from this fantastic event will benefit the Life Choice Pregnancy Care Center of Franklin, KY, making it a wonderful opportunity to whine, wine, and walk for a great cause. Don't miss out on this unforgettable day filled with fun, fitness, and philanthropy!
Whether you're looking to tackle the hill in the competitive Whine Up the Hill Run/Walk or prefer a leisurely pace in the Sip-n-Stroll, there's something for everyone. Plus, kids aged 6-12 can join in the fun with the Grape Gallop Kid's Run! Enjoy complimentary long-sleeve shirts and, for those 21 and older, a commemorative wine glass awaits at the finish line. All proceeds from this fantastic event will benefit the Life Choice Pregnancy Care Center of Franklin, KY, making it a wonderful opportunity to whine, wine, and walk for a great cause. Don't miss out on this unforgettable day filled with fun, fitness, and philanthropy!
Organiser's Description
"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 [https://www.facebook.com/profile.php?id=61574922731177#]
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 [https://www.facebook.com/profile.php?id=61574922731177#]
Races
-
Whine Up the Hill
Incl. $2.80 Fee & Long- Sleeve Shirt
Sat 3rd October 2026 (4:00PM CDT)
$32.80
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 -
Sip N Stroll
Incl. $2.80 Fee & Long- Sleeve Shirt
Sat 3rd October 2026 (4:05PM CDT)
$32.80
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 -
Kid's Run
Incl. $1.90 Fee & T-Shirt
Sat 3rd October 2026 (4:10PM CDT)
$16.90
Fun dash for younger runners! Let them burn off some energy in a safe, shorter course that runs in a loop around the hilltop. This event is open to participants aged 6-12 years old.
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1 Jagni Loop, Park City, 42160, KY, United States
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WHINE UP THE HILL
