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 unforgettable experience at the 2nd Annual Whine Up the Hill on Saturday, October 3rd, 2026, in the picturesque Park City, Kentucky! This exciting event, set against the stunning backdrop of Maple Retreat near Mammoth Cave National Park, invites participants to tackle a challenging hill on a scenic 2.24-mile course.
Whether you’re a competitive runner or prefer to stroll, there’s something for everyone! Join the Whine Up the Hill Run/Walk for a timed challenge that rewards you with breathtaking vineyard views and delightful wine tasting stops along the way. For those seeking a more leisurely experience, the Sip-n-Stroll offers a chance to savor the scenery and indulge in local wines at a relaxed pace. Plus, kids aged 6-12 can participate in the Grape Gallop, a fun dash designed just for them! All proceeds from this fantastic event go to benefit a local nonprofit, so come whine, wine, and walk/run for a great cause while enjoying an afternoon filled with fun, fitness, and fantastic flavors!
Whether you’re a competitive runner or prefer to stroll, there’s something for everyone! Join the Whine Up the Hill Run/Walk for a timed challenge that rewards you with breathtaking vineyard views and delightful wine tasting stops along the way. For those seeking a more leisurely experience, the Sip-n-Stroll offers a chance to savor the scenery and indulge in local wines at a relaxed pace. Plus, kids aged 6-12 can participate in the Grape Gallop, a fun dash designed just for them! All proceeds from this fantastic event go to benefit a local nonprofit, so come whine, wine, and walk/run for a great cause while enjoying an afternoon filled with fun, fitness, and fantastic flavors!
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. 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 [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. 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 [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
