WHINE UP THE HILL

"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): Ta