Massachusetts · Saturday, May 30, 2026
The Chesterfield Gorge Ultra is a running, trail running, and ultra event held on Saturday, May 30, 2026.
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
The Knights of Columbus Council 10195 of Wilbraham is holding its 9th Annual Knights of Columbus 5K Scholarship Race. Perfect for getting the whole family out!
This community-based event began in 2005 as the Peach Festival Road Race and provides the sole funding for our Knights of Columbus College Scholarship program. To date, we have awarded approximately $65,500 in scholarships to local high school students planning to attend college through race participation and the generous donations of our sponsors.
When: Sunday July 20th, 2025
9AM race time. Arrive earlier for registration.
Where: Soule Road School
Race Route: https://www.strava.com/routes/2853601678467827486
Registration:
Before July 17th: <20yr $15, 20+yrs $20
July 17th and after: <20yr $20, 20+yrs $25
Race T-shirt for participants while supplies last
Prizes for best time in age/gender categories!
The Greenfield Triathlon is the longest running triathlon in New England!
Situated in the heart of Franklin County, the Greenfield Triathlon course meanders through the picturesque back roads of Greenfield, passes through the Historic Eunice Williams Covered Bridge, and features swimming in our very own Green River.
Offering both International and Sprint distances for individual athletes as well as two- and three-person teams, the Greenfield Triathlon is great for both beginners and seasoned triathletes. A triathlon training program is offered Sundays leading up to the event. In Greenfield, our motto is “To Finish Is To Win!”
All race proceeds benefit the Greenfield Recreation Department. The Greenfield Triathlon has raised thousands of dollars to support programs and events for families within our community. We thank you for your continued support.
The Mentoring Matters 5K run/walk hosted by the Follow My Steps nonprofit organization aims to raise awareness for the need for mentorship in under-resourced communities. Follow My Steps is a Springfield Massachusetts-based non-profit organization offering Youth Mentoring, Career & Skill Development, and Financial Resources.
YOUTH DISCOUNT APPLIED AT CHECKOUT!!!
This year, we are excited to announce the 5th annual Mentoring Matters 5K will be held at Forest Park.
Note: Registration takes place at the Monkey House.
Park in Cyr Arena Parking lot.
Runners and walkers can register as teams or individuals – and have the option to fundraise as a team.
Tee Shirt included in registration (limited availability)
ABOUT FOLLOW MY STEPS
DID YOU KNOW?
Young Adults Who Were At-Risk for Falling Off Track but Had a Mentor Are:
55% more likely to enroll in college
130% more likely to hold leadership positions.
78% more likely to volunteer regularly
90% are interested in becoming a mentor
Our organization is headed by strong professional who are dedicated to elevating under-resourced students and their families. We understand that there is a disproportionate representation of minorities in key decision-making positions in all facets of leadership in the current time. We aim to close that gap by providing deserving students with the opportunity for financial, mental, and professional education. By offering mentorships to scholarship recipients, we aim to grow a network of like-minded individuals who will continuously give back to their communities and others alike.
VIRTUAL 5K OPTION: #MentoringMatters5K
#MentoringMatters5K is a virtual, non-competitive race by Follow My Steps that allows participants to choose their preferred distance and activity, such as running, walking, or dancing. It can be completed at any time from now until August 8th, and participants are encouraged to share post-challenge photos with the hashtag #MentoringMatters5K. The $40 registration fee serves as a donation to support resources for youth empowerment, including providing school supplies, financial aid for college-bound students, and hosting skill development workshops. Participants are encouraged to track their activity time and distance using a smartphone or smartwatch
THE 2026 MARATHON IS FULL. THERE IS NO WAITLIST AND NO BIB TRANSFERS.
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.