6 running events in Town of Southold, New York

From big races to Saturday morning group runs—find running events and connect with the local endurance sports community.

• Mighty North Fork Triathlon [eventpowerli.com] [Register at runsignup.com]
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  Sun, May 31, 2026 at 6:50 AM

  Description

  This is one of the best first timer courses with a calm Peconic Bay swim, a mostly flat, scenic 7 mile bike and an equally scenic 3.5 mile run. Held in the heart of Long Island’s wine region, this event has something for both athletes and spectators alike.

  Swim: 500 meters, Bike: 7 miles, Run: 3.5 miles

  Start Time: 6:50am

  Run Swim Triathlon

  Bayview Road, Town of Southold, New York, 11971, United States
  OpenStreetMap Google Maps
• Run the Vineyards - Pindar Vineyards 5K [gooddayforarun.com] [Register at runsignup.com]
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  Sun, Jul 26, 2026 at 9:00 AM

  Description

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  Run the Vineyards' 7th Annual Summer 5K at the amazing Pindar Vineyards, a one-of-a-kind property on the North Fork Wine Trail. Enjoy a beautiful 5K through 500 acres of vines and finish with a fun...

  Run the Vineyards' 7th Annual Summer 5K at the amazing Pindar Vineyards, a one-of-a-kind property on the North Fork Wine Trail. Enjoy a beautiful 5K through 500 acres of vines and finish with a fun filled and relaxing after party with live musician and delicious award-winning wine.

  THIS RACE PROUDLY SUPPORTS THE NY CANCER FOUNDATION: Learn More Here: NYCancerFoundation.org

  THE RACE:

  • 5K Chip Timed Race Starts at 9am

  • Beautiful Views through the Vineyard Property

  • Water Station and Friendly Course Volunteers

  • Awards for Top 3 Overall Finishers and Top 3 per Age Group (Male/Female) (14 and under, 15-19, 20-29, every 10yr.)

  • Instant Results available at finish and online

  • Dilly Dilly Donuts will be on site pre-race and post-race with donuts, coffee, and more treats!

  THE PARTY:

  • Relax at the after-party on the pavilion and picnic areas

  • Complimentary Glass of Wine for all participants age 21 +

  • Food Truck on Site with delicious food options.

  • Live Musician performing until noon.

  • Custom Tech Shirts included Men's/unisex, Women's, or Youth Tees or upgrade to Women's Racerback Tank Top for $5 extra. Men's/unisex tank option does not require added fee. *Please register by July 12 to guarantee 1st choice. Many extras ordered and available while supplies last after July 12.

  • Stemless "Run the Vineyards" Wine Glass included.

  • Souvenir Finisher Medals available for $8 during registration or $10 on race day

  OTHER AMENITIES AND INFORMATION:

  • Free downloadable photos

  • Walkers and children are welcome to participate.1 Hour Time Limit. Need to be registered and start on time at 9 AM behind the runners for safety of all participants.

  • Free parking

  • Spectators are welcome. Wine available for purchase on site.

  • Finish Line Water and banana

  • Remember to bring additional water for pre-race hydration.

  • Packet Pick-Up: Race day @ 7:30 AM - 8:30 AM at "Good Day for a Run" tent at the winery next to the pavilion and back parking lot. It is important that you arrive early. Late starts not allowed due to the design of the course/markings change during the race. All participants should be on site by 8:30am.

  • Race is Rain or Shine. No refunds or deferrals.

  Volunteers receive free future race and glass of wine! Visit "Volunteer" tab for details and sign up!

  Invite Facebook friends on the Event page here: facebook.com/events/1287748903412570

  5k Run Trail Walk

  Town of Southold, New York, 11958, United States
  OpenStreetMap Google Maps
• Run the Vineyards - Pindar Fall 5K and 8K [gooddayforarun.com] [Register at runsignup.com]
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  Sun, Oct 04, 2026 at 9:00 AM

  Description

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  Enjoy a Scenic Autumn race through Pindar Vineyards along their 300 acres of vines! Enjoy Live Music, Delicious wine, and Relax in the Pavilion and Picnic areas with views of the beautiful...

  Enjoy a Scenic Autumn race through Pindar Vineyards along their 300 acres of vines! Enjoy Live Music, Delicious wine, and Relax in the Pavilion and Picnic areas with views of the beautiful vineyard...Run the Vineyards 7th Year at this popular North Fork destination!

  THIS RACE PROUDLY SUPPORTS THE NY CANCER FOUNDATION

  The Race Features:

  • 8K and 5K Courses - both lead you through the gorgeous vineyard property. Races start at 9 AM.

  • Flat Course mostly on hard packed dirt trails and short cut grass. Walker friendly, registration required to participate, must start on time behind pack of runners at 9 AM.

  • Professionally Chip - timed with live streamed results.

  • Custom Tech Tee included or upgrade to Long Sleeve Tech for $6 extra. Women's, Men's/unisex, and Youth Tees available. *Please register by Sept. 20. to guarantee first choice of shirt style/size. Many extras ordered and available while supplies last after Sept. 20.

  • Water stations on course and water and bananas at finish line.

  • Awards for Top 3 Overall and Age Group Male and Female Winners (Age 14& under, 15-19, 20-29, and every 10 yrs)

  • Souvenir Finisher Medals available for purchase during registration for $8 or $10 on race day (different design than award medals)

  The After-Party Includes:

  • A Glass of delicious Pindar Wine (21+)

  • Stemless "Run the Vineyards" Wine Glass

  • Live Music immediately following race until 12 pm

  • Spectators welcome. Additional wine available for purchase after race.

  • On site Food Trucks

  • Dilly Dilly Donuts food truck will be on site pre & post-race with donuts, coffee, and more treats!

  • Awards Ceremony starts around 10:15 AM.

  • Free downloadable race and after-party photos. Professional photographer on staff. Photos emailed 24-48 hrs after race.

  Important Race Day Details:

  • Packet Pick-up on Race Day @7:30 AM - 8:30 AM at "Good Day for a Run" tent behind the winery.

  • Arrive before 8:30 AM to pick up race number, shirt, and listen to announcements. Race starts at 9AM.

  • Late arrivals may pick up swag, but may not start onto the course after 9AM start time for safety reasons. Course markings are changed during the race.

  • Walkers and children welcome to participate. Registration required to be on the course for safety of all participants. Walkers should register for the 5K not the 8K in the interest of time. 1 Hour Time limit for 5K. 1 Hour 40 Min Time limit for 8K. Time Limits kindly requested in respect of staff and volunteers' time on the course.

  • Parking is on-site and free. Arrive early to park & allow time for a short walk to the check-in and starting line.

  • Race is rain or shine. No transfers or refunds.

  Volunteers receive complimentary glass of wine & free future race! Visit "Volunteer" tab for details & sign ups!

  5k 8k Run Trail Walk

  Town of Southold, New York, 11958, United States
  OpenStreetMap Google Maps