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
Events
Weather
Typical Conditions
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
82°
Typical Low
57°
Based on US Climate Normals data from Lenox Dale, 14 mi from the venue.
Host City
About East Otis, MA
Elevation
1,542 ft
Nearest Airport
BDL
Bradley International Airport · 26 mi
Time Zone
Eastern Time
From Endurance Grid
Line up lodging and travel early to lock in your race weekend.
Race Location
Your Next Start Line
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at Smile Like Jack 5k/10k/Fun Run, put it on the calendar, and turn “someday” into a start date.
33
Days to train
- Race
- Smile Like Jack 5k/10k/Fun Run
- Date
- July 11, 2026
Coming Up
More Running races near East Otis, MA
2026 Camp Jewell 5K Fun Run/Walk & Kids 1M
Youth
14 miles away
BECCA'S SOLDIERS PRESENT THE 7th ANNUAL FAMILY FUN DAY AND AWARENESS STROLL IN MEMORY OF REBECCA PENNINGTON
13 miles away
Hogsback Half Marathon
Half Marathon
14 miles away
Run Stanley
13 miles away
From Endurance Grid
About This Sport
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.
Frequently Asked Questions (FAQs)
- What is the Smile Like Jack 5k/10k/Fun Run?
- Smile Like Jack 5k/10k/Fun Run is a running race held in East Otis, Massachusetts on July 11, 2026. It is one of the many endurance events listed on Endurance Grid, a multi-sport endurance event calendar covering running races, triathlons, HYROX, and more endurance sports across the United States. Find more running races near you or explore our sports guides to learn what race day actually feels like.
- When and where is the Smile Like Jack 5k/10k/Fun Run?
- Saturday, July 11, 2026 in East Otis, Massachusetts at The Knox Trail Inn, East Otis, MA. Check the 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 the event's registration page. Confirm pricing and distances there, and sign up.
Smile Like Jack 5k/10k/Fun Run
Jul 11, 2026