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  • Distance: 38 km from Montauk
    Sat, Jul 11, 2026 at 9:00 AM

    SATURDAY JULY 11th, 2025 9AM

    $25.00 registration fee includes a tee shirt

    Must register by June 17th to guarantee tee shirt size.

    Benefits the Point O' Woods Recreation Department

    Prizes for the Overall Males and Females

    Youth 15 and Under

    Senior 65 and Older

    Same day registration will be available, no guarantee of preferred T-shirt size

    Online reg closed, can register in person between now and race day

    You must be a resident of Point O' Woods Beach or a friend of a Point O' Woods resident….if a friend or relative you will be required to check in with security at the front gate. No public parking is available in or around the Point O' Woods Beach Association

    See full details
    5kRunWalk via RunSignup
  • South Euclid Avenue, Montauk, New York, 11954, United States
    OpenStreetMap Google Maps
    Distance: 1 km from Montauk
    Sun, Jul 19, 2026 at 6:50 AM

    One of the best finish lines around! Finish your run, leading up to the historic Lighthouse. Swim a 1/2 Mile starting at Gin Beach. This is a beautiful point to point swim. Bike 14 miles through Montauk and around Gosman’s Dock finishing at the lighthouse and run a 5K through wide, closed, paved roads.

    Unique race with two transition areas!

    RunSwimTriathlon via RunSignup
  • Distance: 44.2 km from Montauk
    Sat, Jul 25, 2026 at 8:00 AM

    Celebrate the Midsummer Festival in historic Old Lyme Village with this family friendly event benefitting the Lymes' Youth Service Bureau (LYSB).The Midsummer 5K Run features a scenic road race, a 5K Run & Walk, and a Kids K. The race will begin at LYSB located at 59 Lyme Street and wind through the beautiful streets of the village. The race is held on the morning of the renowned Old Lyme Midsummer Festival, kicking off a weekend of cultural, artistic and community events at multiple sites throughout Old Lyme’s Historic District.

    Pricing for the 5K (run and walk) is $30 for adults, $15 for youth (18 and under). Registration for the "Kids K" fun run is $10. Chip timing will be provided by Fast Track Timing for 5K runners. Commemorative T-Shirts will be available for the first 200 registered participants. Finisher medals for all.

    The overall top three men and women will be recognized as well as the top age group winner in the men and women divisions. Divisions will be broken down as follows: Youth 14 and under, 15 to 19, 20 to 29, 30 to 39, 40 to 49, 50 to 59, 60-69, and 70 plus.

    Online registration closes at 11:59 p.m. on Friday, July 24th. On site registrations accepted up to race day.

    Tee-Shirts for the first 200 registered runners/walkers.

    Pre-Race Packet pick up on Friday, July 24, 9:00-5:00 p.m. at LYSB (59 Lyme Street, Old Lyme)

    RACE DAY: Saturday, July 25, 2026

    Schedule:

    6:45 am – Registration opens

    8:00 am – 5K Run & Walk

    9:00 am – Kids K

    PACKET PICK UP: Friday, July 24, 2026, 9:00 a.m. to 5:00 p.m. OR on Race Day starting at 6:45 a.m.

    Proceeds from the Midsummer 5K will support LYSB's programs for youth and families including mental wellness, drug & alcohol prevention, juvenile justice, positive youth development, and early childhood.

    For more info about LYSB and the 5K contact LYSB at 860-434-7208 www.lysb.org

    For more info about Old Lyme Midsummer Festival visit Midsummer Festival | exploreoldlyme.com

    See full details
    1k5kFun RunRunWalk via RunSignup
  • Distance: 43.7 km from Montauk
    Sun, Jul 26, 2026 at 9:00 AM

    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

    See full details
    5kRunTrailWalk via RunSignup
  • Distance: 42.7 km from Montauk
    Wed, Jul 29, 2026 at 6:00 PM

    The 31st running of the Bottone Mile. Traffic-free one loop course, with no 90-degree turns!

    Bibs and assigned waves (if applicable) will be seeded in order of projected time entered in online pre-registration.

    Cookout and drinks post-race. Pre-registration required.

    1 MilesRun via RunSignup
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