The Whine Up the Hill race starts at 4:00 PM, giving you flexibility if you're traveling in on race day. Held in Park City, Kentucky at 1 Jagni Loop, this event covers 2.24 miles and welcomes both runners and walkers. Entry fees range from $15 to $45 depending on your registration choice. The afternoon start time means you can plan your travel and pre-race meal accordingly without an early morning commitment. Whether you're doing a final shakeout run or prefer a relaxed pace, the relatively short distance makes it manageable as part of a longer race weekend itinerary.
From the Race 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 Follow Us: Follow us on Facebook
Hotels Near This Race
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Race Travel Insurance
Don't forget travel insurance for October 3.
You've trained for months and booked a trip to Park City, KY.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
WHINE UP THE HILL 2026 — Park City, KY takes place on October 3, 2026. The race is held in Park City, Kentucky.
Where is WHINE UP THE HILL 2026 — Park City, KY held?
WHINE UP THE HILL 2026 — Park City, KY is held at 1 Jagni Loop in Park City, Kentucky.
Where can I find hotels near WHINE UP THE HILL 2026 — Park City, KY?
RaceHotelFinder shows hotels sorted by distance from the race venue in Park City. Use the map or list view on this page to compare options and book race weekend accommodation.
