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  • Hudson Valley Marathon [finishers.com]

    Sun, May 03, 2026

    Description

    Ready to take on a new challenge? 🏃‍♂️

    48.1 km from Pittsfield
    City of Hudson, New York, United States
    OpenStreetMap Google Maps

    5k 10k Half Marathon Marathon Run

  • Tails & Trails State Forest Run [facebook.com] [Register at ultrasignup.com]

    Sat, May 16, 2026

    5.8 km from Pittsfield
    1041 Cascade Street, Pittsfield, Massachusetts, 01202, United States
    OpenStreetMap Google Maps

    25k 50k Run Trail Ultra

  • Steel Rail Race [finishers.com]

    Sun, May 17, 2026

    1.9 km from Pittsfield
    Pittsfield, Massachusetts, United States
    OpenStreetMap Google Maps

    Half Marathon Marathon Run

  • Chesterfield Gorge Ultra [finishers.com]

    Sat, May 30, 2026

    32.2 km from Pittsfield
    Hampshire County, Massachusetts, United States
    OpenStreetMap Google Maps

    Run Trail Ultra

  • Smile Like Jack 5k/10k/Fun Run [smilelikejack.com] [Register at runsignup.com]

    Sat, Jul 11, 2026 at 9:00 AM

    Description

    Join us Saturday, 7/11/2026 for our Fifth Annual Smile Like Jack Family Fun Run/Walk. We will have food, beverages (21+ options too), amazing raffles, music, and lots of smiling faces!

    Early check-in...

    Join us Saturday, 7/11/2026 for our Fifth Annual Smile Like Jack Family Fun Run/Walk. We will have food, beverages (21+ options too), amazing raffles, music, and lots of smiling faces!

    Early check-in will be held Friday 7/10/2026, from 4-7 PM at the Knox Trail Inn, for those who wish to get their bibs the evening before.

    Day of registration and check-in begins promptly at 7:00 AM, while the race kickoff is at 9 AM.

    Prices:

    Competitive Race (Chipped Timed) 5k/10k

    $40

    Family Fun Run/Walk (Not Timed)

    $35

    We hope to see you there!

    Cutoff for T-shirts will be June 1st. This event is rain or shine!

    JACK'S STORY

    The Smile Like Jack Memorial Fund was established in memory of Jack William O’Brien, a loving son and brother, caring friend, and hard working young man that touched the lives of many with his contagious smile. Jack tragically passed away in a snowmobile accident on March 3rd, 2022. In his 20 short years, he had accomplished many things and leaves behind a legacy that is in a caliber of its own. Jack lived life to the fullest. He was always working exceptionally hard to accomplish his set of goals while also living the outdoorsman lifestyle: fishing, hunting, and riding. Our goal is that the Smile Like Jack Memorial Fund will bring other individuals (with similar passions) the opportunity to live their legacy just as Jack would - working immensely hard in the trades and living life to the fullest in the great outdoors.

    For additional information on The Smile Like Jack Memorial Fund, and for live updates, please visit our website: https://smilelikejack.com

    35.3 km from Pittsfield
    Berkshire County, Massachusetts, 01029, United States
    OpenStreetMap Google Maps

    3.1 Miles 5k 6.2 Miles 10k Fun Run Run Trail Walk

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