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3 running, duathlon, and walking events in East Islip, New York

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

  • Heckscher Classic 7 & 14 Mile Trail Race [runsignup.com]

    Sun, Mar 29, 2026 at 9:00 AM

    Description

    Run the scenic perimeter of Heckscher State Park in the Heckscher Classic! Choose between a 7-mile or 14-mile course on smooth, runnable trails. Perfect for both new trail runners and experienced...

    Run the scenic perimeter of Heckscher State Park in the Heckscher Classic! Choose between a 7-mile or 14-mile course on smooth, runnable trails. Perfect for both new trail runners and experienced athletes.

    The course follows the perimeter of Heckscher State Park in a clockwise direction and will be clearly marked.

    This event is one step up from a fat ass–style run. Timing will be done by hand, and a basic aid station with water and light snacks will be available at the start/finish area (mile 7).

    Each participant will receive a finisher’s medal, and awards will be given to the top three male and female finishers in each distance. Participants will also receive a Heckscher Classic Bucket Hat!

    Participants in the King of the Hill 3-Hour Run on March 7th at Sunken Meadow State Park will receive $10 off race registration.

    7 Miles 14 Miles Run Trail

    77 Timber Point Rd, East Islip, New York, 11730, United States
    OpenStreetMap Google Maps
  • Chasing the Rainbows Bursting Bubble 5K Walk & Run — East Islip, NY [runsignup.com]

    Sun, May 03, 2026 at 9:00 AM

    Description

    Event Date: May 3, 2026 • 9 AM to 12 PM

    Join Chasing the Rainbows this Bereaved Mother’s Day weekend for the Busting Bubble 5K Walk & Run, a heartfelt event dedicated to healing, remembrance, and...

    Event Date: May 3, 2026 • 9 AM to 12 PM

    Join Chasing the Rainbows this Bereaved Mother’s Day weekend for the Busting Bubble 5K Walk & Run, a heartfelt event dedicated to healing, remembrance, and community. Whether you join us in person at one of our many locations or participate virtually, your involvement helps raise awareness and provides vital support for families grieving infertility, pregnancy loss, stillbirth, or infant loss.

    Why Bubbles?

    Bubbles symbolize the many shapes and moments of grief, unexpected, unique, and deeply personal. Just as bubbles reflect rainbows in the light, they remind us of the signs, love, and connections our babies continue to send. These brief glimmers of color reflect the memories that stay with us forever.

    Our Purpose

    To raise awareness and offer essential support to families grieving the unimaginable.

    Your Impact: Supporting 11 Daily, Free, Trauma Informed Services

    By registering, you directly support Chasing the Rainbows’ 11 free services that offer daily, compassionate care. These include virtual support groups held four times a day for a total of eighteen sessions each week, in-person support groups throughout the United States, peer mentors, trauma therapy, the Cry It Out Loud podcast, coping care packages, mindful movement, online private chat communities, resources for family members, perinatal bereavement training for medical units, and community events. These programs ensure that no one has to navigate grief alone.

    A Celebration of Life

    This event is more than a walk or run. It is a joyful and healing gathering filled with live entertainment, vendors, and sponsors. Together, we will celebrate the lives of the little ones we carry in our hearts and the strength of those who love them.

    The Wall to Remember

    We will feature a Wall to Remember, a touching tribute honoring babies gone too soon. It offers a space for reflection, connection, and remembrance.

    Get Involved

    You can make an even greater impact by becoming a donor, personal sponsor, or company sponsor. Your generosity helps sustain the services families rely on every day. To get involved or volunteer, contact us at [email protected] or visit chasingtherainbows.org. Every step taken, every bubble released, and every story shared helps bring healing and hope. Register today and help us honor, remember, and support families on this meaningful day.

    5k Run Virtual Walk

    1 Heckscher State Pkwy, East Islip, New York, 11730, United States
    OpenStreetMap Google Maps
  • Mighty Mother's Day Du and Time Trial [eventpowerli.com] [Register at runsignup.com]

    Sun, May 10, 2026 at 8:35 AM

    Description

    The Mighty Mother's Day Duathlon is a great way to start your season! This event has been a mainstay on the multi-sport scene for over 20 years with a very flat 3 lap bike course and some grass and...

    The Mighty Mother's Day Duathlon is a great way to start your season! This event has been a mainstay on the multi-sport scene for over 20 years with a very flat 3 lap bike course and some grass and dirt on the run.

    Celebrate the ladies in your life! Sparkling cider, chocolate and awards await you at the finish line!

    Adult Race: Run: 1.8 miles, Bike: 10.5 miles, Second run: 1.8 miles

    Start Time: 8:30am

    Time Trial Start: 8:32am. This is the bike portion only.

    You are not guaranteed your t-shirt size if you register after May 4th.

    3 Miles 10.5 Miles 14.1 Miles Duathlon Run

    1 Heckscher State Pkwy, East Islip, New York, 11730, United States
    OpenStreetMap Google Maps
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