Smile Like Jack 5k/10k/Fun Run
- Date
- July 11, 2026
- Distance
- 5k · 10k · Family Fun Run/Walk
From the Organizer
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
Distances & Pricing
Race Location
About This Sport
From Endurance Grid's Founder
Endurance Grid is here to help you understand the sport, decide if it's the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer's event page.
The 10K is the distance where running stops feeling like a starting point and starts feeling like a sport. Long enough to require a real training block. Short enough that race day is fully manageable for a first-timer who's put in the work.
Race day energy at a 10K is community at its best — strangers cheering you by name, people moving toward the same goal, an atmosphere that solo training can't replicate. It's fast enough that you'll spend the whole race pushing rather than managing your effort.
This is also the distance that builds the base for everything else. Most athletes who go on to run half marathons, do triathlons, or compete in HYROX started here. What you need: running shoes fitted to your stride, a training plan, and the race on your calendar. The registration is what makes the deadline real.
How long to train: 4–8 weeks for most fitness levels.
Running
From 5K to marathon, running races are the most accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Coming Up
More running races in MA
Registration Link has changed: https://events.elitefeats.com/26blackexcellence (Copy and paste the link in your browser or click the link in the description)
5K
Summer Classic 5K
5K
Miles Over the Moon
5K and Fun Run for Jabberwocky
5K
Frequently Asked Questions (FAQs)
- What is the Smile Like Jack 5k/10k/Fun Run?
- Smile Like Jack 5k/10k/Fun Run is a running event held in East Otis, MA. Learn more about the different endurance sports here.
- When and where is the Smile Like Jack 5k/10k/Fun Run?
- Saturday, July 11, 2026 in East Otis, MA at The Knox Trail Inn, East Otis, MA. Check the official event page for exact start times and wave schedules.
- How do I register for the Smile Like Jack 5k/10k/Fun Run?
- Registration is handled through their official registration page. Confirm pricing, distances available, and sign up there.
Smile Like Jack 5k/10k/Fun Run
Jul 11, 2026