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  • Chesterfield Gorge Ultra [finishers.com]

    Sat, May 30, 2026

    17.4 km
    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

    36.9 km
    Berkshire County, Massachusetts, 01029, United States
    OpenStreetMap Google Maps

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

  • New England Green River Marathon [newenglandgreenrivermarathon.com] [Register at raceroster.com]

    Sun, Aug 23, 2026 at 7:00 AM

    Description

    The New England Green River Marathon is one of the most beautiful races in New England. Starting in Marlboro, Vermont and following the course of the Green River through an 1870’s covered bridge, and...

    The New England Green River Marathon is one of the most beautiful races in New England. Starting in Marlboro, Vermont and following the course of the Green River through an 1870’s covered bridge, and ending with a finish-line celebration in the shade of maple trees at Greenfield Community College in Massachusetts. This USATF-certified (Certification MA18003JK) course has a net 1,400 foot drop over a rolling, downhill course that has seen many personal best and Boston qualifying times for well-trained runners. Choose below from either the regular entry, OR if you want to support the Connecticut River Conservancy by raising an additional $250, join the Stream Team! This funding will go directly to the CRC for their efforts to restore and advocate for clean water, healthy habitats, and resilient communities to support a diverse and thriving watershed.

    34.9 km
    Greenfield Community College, College Drive, Greenfield, Massachusetts, 01301, United States
    OpenStreetMap Google Maps

    42k Marathon Run

  • Run Stanley [stanleypark.org] [Register at runsignup.com]

    Sun, Oct 04, 2026 at 10:00 AM

    Description

    Come Run, Stroll & Roll! Stanley Park will be hosting the 14th Run Stanley. Run Stanley has grown into a fun yearly tradition for the whole family, whether they like to run, walk, roll, or bark. Join...

    Come Run, Stroll & Roll! Stanley Park will be hosting the 14th Run Stanley. Run Stanley has grown into a fun yearly tradition for the whole family, whether they like to run, walk, roll, or bark. Join us for this all-inclusive event on Sunday, October 4, 2026 at 10:00 am at Stanley Park. This event includes the 5K trail run/walk, a 5K K9 trail run/walk, the Munchkin Run hosted by Dunkin’ Donuts, and The Stroll & Roll. The Stroll & Roll is a wheel friendly a 1-mile non-competitive walk through Stanley Park’s accessible pathways.

    The school with the most Munchkin Run participants wins the coveted “Stanley Cup School Spirit Trophy,” which will be displayed at their school for the entire school year!

    The race will help to raise funds to benefit the care and upkeep of the Frank Stanley Beveridge Wildlife Sanctuary, Stanley Park and its accessible pathways. Please join the community of runners, walkers, hikers, dog owner and nature lovers who love Stanley Park.

    Register by September 18, 2026 to be guaranteed a T-shirt.

    Run Stanley Race Day Schedule:

    Late Registration: 9:00am - 10:00am at Children’s Pavilion

    T-Shirt & Bib Pickup: 9:00am -10:00am at Children’s Pavilion

    Vendor Village 9:00 am - 12:00pm

    Kids' Munchkin Warmup: 9:30am

    Kids’ Munchkin Run: 10:00am

    K9 5K Run/Walk : 10:20am

    The Stroll & Roll (1-mile accessible stroll): 10:20am

    5K Run/Walk: 10:25am

    If you are interested in volunteering please use this link: https://docs.google.com/forms/u/0/d/e/1FAIpQLSennZ3hM8TJO4yhvKixTReyrAHMdx-8FxWkBz97NcEQiH2etw/formResponse

    Prizes will be awarded for the following categories and mailed to the winners:

    1st Place Male and Female 5k Student Run/Walk

    1st Place Male and Female 5k Run/Walk

    1st Place Male and Female K9 5k Run/Walk

    Oldest and Youngest Finisher of 5k Run/Walk

    49.5 km
    Westfield, Massachusetts, 01085, United States
    OpenStreetMap Google Maps

    1 Miles 3.1 Miles Run Trail Walk

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