2024 Happy Tail Wine Trail 5k

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Points count towards 5k & Back of the Pack Series.  Points count towards Sippin’ Series.  Find more info about the series here.

Register Now!

Please note that Bishop’s Events promo/discount codes can not be used to register for this event.

Walkers are welcome to attend this event.  Strollers are welcome, but course may not be suitable for the average stroller.

1 mile fun run is for runners ages 5 – 13.

Dog Jog:  Want to bring your pup for a bit of exercise? We have a great 1 mile course just for you that you can jog or walk as you like. Dogs must be current on vaccinations and medically fit to handle a 1 mile walk. Please make sure your fur babies can handle a crowd because we want them to feel comfortable and have fun too!

Homestretch Mosey:  Want to say you’re doing a race for charity but really want to minimize the effort? Join us for the Homestretch Mosey where you take a stroll down the homestretch and still get all the swag and wine! It’s only 100 feet for the animals!

Virtual Race Option

We now offer a virtual run option for those who cannot make it on race day.  Find more information about our virtual option on our Virtual Races page.


Runners Receive

1 Glass of wine from 53rd Winery, Finisher’s Medal, Technical (Drifit) Event Shirt, & A Chip Timed Event


Charity Information

This is run benefits the Louisa Humane Society, a non-profit 501 (c)(3) organization. Last year we spent over $80,000 to feed, spay and neuter, and provide medical care for our animals. We depend on fundraisers and the generosity of our community for much of our budget and proceeds from this race will go to saving more lives. Thank you for signing up. We hope you have fun, enjoy the refreshing wine, and think of us the next time you are looking for a furry new member of the family!


Race Start Times

1m fun run – 8:45am

5k – 9:00am

1m dog jog – 9:15am

Hometown Mosey – 9:15am


Registration Fees

5k – $30, until April 15 ($40)

1m fun run – $25, until April 15 ($30) – open to ages 5 – 13

1m dog jog – $30 until April 15 ($40)

Hometown Mosey – $30 until April 15 ($40)

T-shirts guaranteed to runners registered before May 15.  We will order extra t-shirts for those who register after that date, but it is on a first-come first-served basis.


T-Shirt Design

T-shirt design for the race is available here as soon as it has been approved.


Race Medal Design

Race medal designs can be viewed on the Friday before the race on the Bishops Events Facebook page or our Instagram page.


Course Maps can be found at

This is a cross country route around the outside of the vineyards and around the winery property. This is a fairly flat route, but you can find elevation gain on the course map page.


Live Race Results

Live results will be posted on Athlinks.com.  Additionally, there will be a QR code at the race for you to scan to immediately view your results.  Final race results with series points will be posted to our website on the Monday following your race.

Runner tracking is now available when you sign up for a race with Bishop’s Events. Click on the green SMS button (see example below) at the end of your registration and have your race updates sent to your mobile device as well as those of your friends & family so they can track your race progress.



We award the top 3 men and women overall during our awards ceremony post-race.



We will post any photos taken by staff on our Facebook page by Tuesday after the event.


Social Media Challenge

On Tuesdays, we pick our favorite Instagram or Facebook post from the previous race weekend.  The winner will receive 50% off a future race!  Make sure to tag us in your race photos at:

Instagram:  BishopsEventsLLC

Facebook: BishopsEvents


Packet Pickup

Packet pickup is available at the event.  We recommend arriving one hour before your event start time to check-in.


Race Day Registration

There will be race day registration. Participants will need to arrive approximately one hour before the race to register for the event. T-shirt sizes cannot be guaranteed for race day registers.

***Price will increase on race morning by $5 for each distance


Water Stations

Two water stations will be along the 5k course at approximately mile markers 1 & 2.  Gatorade will be available at some water stations.  Water stations are subject to change as deemed necessary.



Restrooms can be located inside the winery.



Volunteers should arrive approximately 60 minutes before the first race kicks off.  We will assign volunteer tasks on race morning (water station, course marshals, finish line support, etc).  You can find parking information under “Directions to Parking” with a latitude and longitude pin for where to meet.


Weather Policy

We are an all-weather race company (rain or shine or sleet or snow). We will email registered runners and post on social media if the race is cancelled, but this is quite rare, otherwise assume the race is taking place as scheduled.

Weekly weather reports are posted on the Thursday before race weekends on our Facebook page by Chad Merrill with the Hagerstown Almanack.  Race officials may delay, change or postpone the event due to weather conditions.  All registered runners will be notified via email of any changes.  In most cases, a decision is not made until the night before the race, and a decision could come as late as the morning of the event.


Refunds & Transfers

To view our full refund/transfer policy, click here.


Directions to Parking

The race starts and ends at 53rd Winery (13372 Shannon Hill Rd, Louisa, VA 23093).  The best way to locate this event is via GPS using this latitudinal and longitudinal pin: 37.960127, -77.924066