Sun December 18, 2022 Oxford, FL 34484 US Directions


$35 8:30AM EST - 10:00AM EST Price increases after December 7, 2022 at 11:59pm EST
Open to ages 1 - 99.

Like Running or Walking?  Love Wine?  This race is for you! 

Join us on Sunday, December 18, 2022 for an exciting "Christmas Themed" event that features the scenic views of Whispering Oaks Winery and offers a great assortment of locally produced wines!   Due to the huge turnout for this event, we will be offering 2 start times at 8:30am and 10am.  Please make a selection for your wave during signup.

With extra swag options for all wine lovers, walkers and runners, this race is a sure thing for a great time!  This race is timed and scored by J3 Timing.  Results will be posted at

Registration Includes:

  • T-shirt:  Super Soft Ring Spun Cotton t-shirt included! Optional long sleeve upgrade for an additional $5 dollars!
  • Wine Glass: White Christmas Tumbler
  • Finisher Medal (doubles as a Christmas ornament)
  • Race Bib: Chip timed 5k run/walk
  • Results Posted Online
  • ...and of course, a pour of wine!
Race Swag



Let's Do This!

Our professional photographer uploads race pics online for FREE DOWNLOAD after the event!  



Team Bonuses

Refer Friends = Earn Cash Back!

How It Works:

1) When registering, create a Team Name for your group.  Create a password (and write it down!)

2) Tell all your friends to sign up for the race!  (be sure to give them your team name and password)

3) When your Team hits 5 participants, the first 4 members will get $5 CASH BACK and the 5th member will receive a $5 discount off their registration!

4) If you have a team of 10, every new team member gets $5 CASH BACK and the team leader will receive 1 bottle of wine at the specified winery.

5) If you have a team of 20, every new team member gets $5 CASH BACK and the team leader will receive a total of 5 bottles of wine at the specific winery.

Whispering Oaks Winery
10934 S Hwy 475
Oxford, FL US 34484
Course Map

There will be vines, and there will be wines!

Get ready for an awesome and scenic 5K tour of the vineyards!  If you're looking for a personal best time, this is not the course for you!  But if you're looking for a personal best wine this course is a guaranteed winner!  The course is mostly grass and dirt.  

We are proud to announce that the local charity partner for this event is The Florida Sheriffs Youth Ranches!

Founded in 1957, The Florida Sheriffs Youth Ranches has been improving the lives of at-risk children through its seven Florida locations and comprehensive programs. The Sheriffs Youth Ranches is credited with helping more than 165,000 children and families in Florida.

Funds raised from this event will go directly to Sumter County's Youth Ranch Program!

Click here for more information!

Age Group Awards and More Info

This event will be offering Age Group Awards!  In addition to scoring all of the great swag listed above, the top 1 finisher in each age category also receives a custom age group award!   

5 Year Categories: 14 & Under, 15-19, 20-24, 25-29, 30-34, 35-39, 40-44,. 45-49, 50-54, 55-59, 60-64, 65-69, 70-74, 75-79, 80 & Over

Important details: 

  • Competitive Runners, please start with the first group to be eligible for an age group award. 
  • If your event has wave start times, age group winners must start with the first wave to be eligible for a medal. 
  • There will be no age group ceremony.  Please look up your results at after finishing and if you placed top 1 in your category please visit the registration table to pick up your award.
  • Age Group medals will be available for pickup 1 hour after the start of the first wave  - age group awards are only available the day of the event and will not be available for shipment once the event has concluded.

5 Year Categories: 14 & Under, 15-19, 20-24, 25-29, 30-34, 35-39, 40-44,. 45-49, 50-54, 55-59, 60-64, 65-69, 70-74, 75-79, 80 & Over


Is the race only for 21+? No, minors are welcome to participate and receive a discounted registration that includes a shirt, medal and bib (these participants will not receive a wine glass or a glass of wine).
Are strollers allowed? You are welcome to use a stroller for this event but it is not recommended due to uneven ground on the course and children in strollers can participate for free and do not need to register.
Is walking allowed? Yes Absolutely!  We get as many if not more walkers at this event than we do runners!
Is the race dog friendly? Unfortunately, dogs aren't allowed at this race.
I still have questions, who do I contact?  If you cannot find the answer to your question on this page please use the "questions" button on this page to submit a question. 

Run for the Wine... Stay for the Fun!

Following the 5k Run/Walk, Whispering Oaks Winery will have Food, Wine, and Live music from 10am-2pm!

Enjoy a great lunch with your fellow runners, friends and family after the event.

Also, Whispering Oaks Winery is offering 10% off Dinner for Two for their Award Winning Friday and Saturday night Steak Night!   

Travel Accomodations

Many participants make this event into a destination weekend!  Our suggested hotel stay is 

Holiday Inn Express & Suites Wildwood – The Villages          

928 E. SR 44

Wildwood, FL  34785

Located just 5 minutes from the winery, features 11 restaurants within walking distance, outdoor pool and whirlpool, fitness center, complimentary breakfast, and more! 

RV and Campers - Whispering Oaks is also a Harvest Host Site - so if you want to stay at the Winery Friday or Saturday and have a harvest host membership join us for the camping party!

Packet Pickup

Packet Pickup will be 5-7pm on Saturday December 17th at Whispering Oaks.   


We highly recommend skipping the lines and enjoying the wines by picking up early!


Can I pick up for my group?  Yes!  Just have them forward you their packet pickup QR code 
Is Race Day Pickup Available?  Yes (starting at 7:30am), but if possible please have someone pick up your packet Friday


Check out the Winery
Can I Participate Virtually?

Absolutely!  We have been getting many inquiries about virtual participation and have integrated a virtual option into our regular registration.

Please feel free to register through the regular registration link above and you can either: 

1) Pick up packet during packet pickup or on the morning of the race, but run on your own (hint:  wine ticket is still good if you use this strategy)

2) Contact us at any time to switch to the Running on Wine and Christmas Cheer Virtual Races and we'll ship your packet. A shipping and handling fee will apply.


Professionally Timed By
Race Contact Info

If you have any questions about this race, click the button below.

Race Website

Additional race information can be found at


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