15 running, walking, cycling, and other events in Springfield, Massachusetts

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 Ride-to-Remember XV promises to again, be the best Charity Bicycle Ride in New England!

This year we are dedicating the R2R to the heroes of the 9-11 tragedy. This year will be the 25th Anniversary of 9-1,1 and we will be stopping at three 9-11 Memorials.

We will be starting again this year from Main & Boland Way in the middle of downtown Springfield. We will be escorted by 35 Police Officers on motorcycles. The group of riders will stay together in one big peloton, you'll never have to clip out of your pedals till we reach our rest-stops. Speaking of rest-stops … Our first official rest-stop will be the New England Air Museum in Windsor Locks, CT. They are rolling out the red carpet for us with a 911 theme.

There are three amazing rest stops along our scenic, New England, 75 mile route. Bike mechanics following us, if you get a flat, we fix it in minutes free of charge. You will be fed breakfast, lunch andf dinner. There is a huge after-party immediatley following the ride at Tower Square in downtown Springfield. We will have a great headlining band to dance and celebrate after you shower, steam, or sauna right inside Tower Square. If you're sore during the ride, we have licesnsed masseueses at the rest stops.

You will be provided with a link to order your Official Ride-to-Remember Bicycle Jersey soon.

We take care of you the entire day … From free parking, bike support, awesome swag, food, hydration and an amazing route! After this ride you will thank the organizers for a very memorable day.

On Saturday, September 19, 2026 the Run/Walk starts at 10:00 AM.

Colby’s Path to the Cure, a 5k run/walk, to raise funds for Synovial Sarcoma Research and Awareness.

King Phillip's Stockade

70 Columbus Ave, Springfield, MA 01105

All registered participants receive T-shirts, sizes not guaranteed; the last day of early registration is 8/31.

Adults: $35, Cost for children 13U $15.00 (Discount appears at Checkout)

As of 9/1, the Registration fee for adults is $40, which may include a t-shirt while supplies last; sizes are not guaranteed.

*******************************Register at this site any time before the start *********************

*****Free Parking is throughout King Phillip's Stockade *****

We will be gathering at the Pavilion closest to the entrance.

Following the race, there will be an outdoor family-friendly gathering at the Pavilion. There will be Music provided DJ. C-Smooth, raffles, face painting, and fun lawn games.

You’ll have the option to purchase a “boxed” lunch or bring your own picnic.

You will be able to purchase a boxed lunch provided by AC Main Street Market with registration (until 09/03) or independently by clicking here:

Choice of Turkey, Cold Cut, Ham, and Roasted Veggie

Feel free to reach out with any questions.