Whispering Oaks Cheers to New Year's 5K
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Event overview
Whispering Oaks Cheers to New Year’s 5k takes place on Saturday, January 3, 2026 in Oxford, Florida at Whispering Oaks Winery (10934 S Hwy 475, Oxford, FL 34484). The event offers in-person and virtual participation options. Registration prices listed for the in-person events include a base price of $35 for the 5k (reduced to $25 for ages 1-20) and $35 for the 1.5 mile walk; prices increase after December 5, 2025. The 5k is open to ages 1 to 99.
Distances
- 5k
- 1.5 Mile Walk
Course and logistics
The course starts and finishes at the winery and uses trails through the property. It is described as a mostly cross-country style route run as a two-lap course. The event is timed and scored by J3 Timing, with results posted by that timing provider. Packet pickup is available the day of the event only and begins one hour before the event.
Awards, photos and other notes
Top three finishers male and female in each 10-year age category receive custom age-group awards; categories span 1-9, 10-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70-79, and 80+. Age-group awards must be picked up on event day; they will not be shipped. Professional race photos will be uploaded for free download after the event. The event lists the Humane Society of Sumter County as its local charity. Strollers are allowed but not recommended due to uneven ground; dogs are not permitted. Minors receive a discounted registration package that does not include a wine glass or a glass of wine. Visit the organization's website for the most recent information.
