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Smile Like Jack 5k/10k/Fun Run logo

Smile Like Jack 5k/10k/Fun Run

Sat, Jul 11, 2026, 9:00 AM EDT

Location
East Otis, MA
The Knox Trail Inn, 1898 E Otis Rd, 01029
Type
RUN
Official registration

Sign up and verify details on the organizer’s official page.

Vibe analysis coming soon

Course feel, difficulty, and community fit are being added to this listing. Check back, and always confirm details on the official registration page.

At a glance

Great for

  • For a Cause
  • Family Friendly

Great for: families

Auto-drafted from the public listing — confirm details on the official event page before signing up.

Distances & registration

3 options

Registration for all distances is through the official signup link above.

  • 3.1 Miles

    Sat, Jul 11, 9:00 AM EDT · From $43.40

    Opens Feb 1, 2026, 12:00 PM EST · Closes Jul 11, 2026, 5:00 AM EDT

  • 6.2 Miles

    Sat, Jul 11, 9:00 AM EDT · From $43.40

    Opens Feb 1, 2026, 12:00 PM EST · Closes Jul 11, 2026, 5:00 AM EDT

  • Family Fun Run/Walk

    Sat, Jul 11, 9:00 AM EDT · From $38.10

    Opens Feb 1, 2026, 12:00 PM EST · Closes Jul 11, 2026, 5:00 AM EDT

Vibe Check

Steady Effort

warm-day exposure

  • Warm season

Based on terrain, weather, and distance data.

The course

  • —
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

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