Run Through the Vines, Then Raise a Glass at Stonington’s Turkey Trot 5K
At a Glance
What: Stonington Vineyards Wine Run Turkey Trot 5K
When: Sunday, November 8, 2026, 10 a.m.
Location: Stonington Vineyards, 523 Taugwonk Road, Stonington, CT
Admission: $53.99 including registration fee; $28.49 for ages 1–20
Registration: Sold out; waitlist available
Distance: 5K (3.1 miles), timed run or walk
Course: Two-loop cross-country route through the vineyard, with some uneven ground
Age: All ages welcome; wine service restricted to eligible adults 21 and older
Included: Race T-shirt, finisher medal, race bib, online results, and wine-related gifts for eligible adults
Food: Dem Boyz Grill and Little B’s BBQ
Charity Partner: Connecticut Chapter of the Alzheimer’s Association
Packet Pickup: Saturday, November 7, 3–4:45 p.m., or Sunday beginning at 9 a.m.
Weather: Rain or shine; severe weather may delay the start
Accessibility: Walking permitted; strollers allowed but not recommended because of uneven ground
Pets: Friendly leashed dogs welcome outdoors
More Info: WineRun5k.com
Course Map
The course will begin and end at the winery. There will be vines and there will be wines! This is a 2 lap cross country style route that starts by heading down the lane then comes back for a few loops through the vineyards. There are some areas of uneven footing but it is very suitable for both runners and walkers.
Event Description
Stonington Vineyards Wine Run Turkey Trot 5K combines a morning run through the vines with a post-race glass of wine on Sunday, November 8. Beginning at 10 a.m., the Thanksgiving-themed event welcomes runners and walkers to the Stonington countryside for a 3.1-mile course, commemorative race gifts, and a chance to celebrate at the winery afterward.
The event has already reached capacity, but interested participants can join the official waitlist to be notified if a space becomes available.
A 5K With a Vineyard View
Forget city streets and crowded intersections. This race begins and ends at Stonington Vineyards, taking participants along a two-loop cross-country course that winds through the property.
The route starts down the vineyard lane before returning for loops among the vines. Along the way, runners and walkers will encounter some uneven ground, adding a little extra challenge to the autumn outing.
There’s no need to be a competitive runner to enjoy the event. Walking is welcome, and participants can complete the course at a pace that suits them.
The race will be professionally timed and scored by J3 Timing, with results posted online.
A Medal That Doubles as a Wine Stopper
This Turkey Trot offers more than the usual finish-line keepsakes.
Registered adult participants receive a soft cotton race T-shirt, a collapsible wine glass, a finisher medal that doubles as a wine stopper, and a wine pour.
The race also recognizes the top three male and female finishers in each age division with custom awards. Winners can collect their awards at the registration table after results become available.
Younger participants are welcome, too. Their discounted registration includes a shirt, medal, and bib, but no wine glass or alcoholic beverage.
Food Trucks and a Cause Worth Supporting
After crossing the finish line, participants can stick around to enjoy the vineyard atmosphere.
Dem Boyz Grill and Little B’s BBQ are scheduled to serve food during the event, giving runners and spectators an opportunity to enjoy a meal after the morning’s activity.
The race also has a charitable connection. The Connecticut Chapter of the Alzheimer’s Association is the event’s local charity partner, supporting an organization dedicated to Alzheimer’s care, education, and research.
What Participants Should Know
The race begins at 10 a.m. on Sunday, November 8.
Advance packet pickup is available at Stonington Vineyards on Saturday, November 7, from 3 to 4:45 p.m. Participants who cannot make that session may collect their materials on race morning beginning at 9 a.m.
The event will take place rain or shine, although severe weather or lightning could delay the start.
Friendly dogs on leashes are welcome, but they cannot enter the winery building. Strollers are permitted, although the organizers caution that the uneven course makes them less practical.
Children riding in strollers may participate without registering.
With the race currently sold out, anyone still hoping to participate should visit the official registration page and join the waitlist.
For those already registered, it’s an opportunity to enjoy a crisp November morning outdoors, take in the vineyard scenery, and finish with a well-earned celebration.
Featured image is an artistic representation inspired by the event and may not depict the actual people, location, or activities shown.ng