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Smile Like Jack Memorial Fund

@smilelikejack

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The Smile Like Jack Memorial Fund has been established to honor Jack William O’Brien’s legacy as an avid outdoorsman. 🎣 🏹
🏃‍♂️2026 Road Race on 7/11

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2 months ago

A HUGE thank you to everyone who came out to support the 2026 Smile Like Jack Memorial Fund road race 🏃🏻‍♀️🏃🏽🏃‍♂️

This year we had over 700 sign ups! We are SO incredibly grateful for each and every participant, sponsor, vendor and volunteer who came out to honor the life and legacy of Jack William O’Brien🤍

Thank you for another great event! We can’t wait to see you all again next year!

Head to the link below for some awesome pictures taken by @vincentcarusophotography 📸

🔗 https://www.vincentcarusophotography.com/smile-like-jack-2026 taken in The Berkshires by @smilelikejack

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3 months ago

Good morning from Knox on the Dock! We are open and ready for the race today! Come early, grab a bite to eat and we've got lots of seating for you to cheer on everyone in the Smile Like Jack Run/Walk today! @smilelikejack @knoxonthedock taken in KNOX TRAIL INN by @smilelikejack

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3 months ago

ONE. MORE. DAY! 🏃‍♂️🏃🏻‍♀️🏃🏽

We can’t wait to see everyone tomorrow! See below for some important race updates!🩵

🚨Important Reminders:🚨

✔️ Pre-Registration / Bib & shirt pickup: July 10th, 4pm-7pm at the Knox Trail Inn parking lot!

✔️ Event day check-in: July 11th, 7:00 AM at Knox Trail Inn parking lot!

✔️ Race check-in will end promptly at 8:50 AM🚨!

✔️ Race kickoff: 9:00 AM!

✔️ Raffle tickets: $20/sheet or $50/3 sheets. Still accepting donations!

✔️ We love your furry friends, but we kindly ask that this event remains dog free !🐾

🎟️ Please note: you must be at the race in-person to play the raffle and win!

Sign up for the race using the link in our bio or below!
🔗 https://runsignup.com/Race/MA/EastOtis/SmileLikeJack taken in KNOX TRAIL INN by @smilelikejack

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3 months ago

The final countdown is on!! 🗓️

We can’t wait to see you on Saturday!!🤍

🚨Important Reminders:🚨

✔️ Pre-Registration / Bib & shirt pickup: July 10th, 4pm-7pm at the Knox Trail Inn parking lot!

✔️ Event day check-in: July 11th, 7:00 AM at Knox Trail Inn parking lot!

✔️ Race kickoff: 9:00 AM!

✔️ Raffle tickets: $20/sheet or $50/3 sheets. Still accepting donations!

🎟️ Please note: you must be at the race in-person to play the raffle and win!

Sign up for the race using the link in our bio or below!
🔗 https://runsignup.com/Race/MA/EastOtis/SmileLikeJack taken in Otis Reservoir by @smilelikejack

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3 months ago

3. MORE. DAYS.🏃🏻‍♀️🏃‍♂️🏃🏽

Swipe to see the food & drinks that our friends @theknoxtrailinn will be providing during race day!! A huge thank you to The Knox for all of their incredible support! 🍔🍻

Sign up at the link in our bio or below! We’re ready to have some fun & want you there to join us!!🤍

🔗 https://runsignup.com/Race/MA/EastOtis/SmileLikeJack taken in KNOX TRAIL INN by @smilelikejack

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3 months ago

4 more days! 🗓️

Who’s excited?! We’re excited! The countdown is seriously on!! Join us at the 2026 Smile Like Jack road race on Saturday, July 11th!! 🤍

🎟️RAFFLE UPDATE🎟️

Swipe to see another amazing raffle prize!! This “Blind Date with a Book” prize was generously donated by the Tonlino family! Thank you!📖

There’s still time to sign up for the fun! Sign up for the race at the link in our bio or below! 🏃🏽🏃🏻‍♀️🏃‍♂️

🔗 https://runsignup.com/Race/MA/EastOtis/SmileLikeJack taken in The Berkshires by @smilelikejack

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3 months ago

5 MORE DAYS!!

The 2026 Smile Like Jack Memorial Fund road race is right around the corner! We can’t wait to spend the day honoring Jack with you all!! 🏃🏽🏃‍♂️🏃🏻‍♀️

🎟️RAFFLE UPDATE🎟️

Swipe to see another AMAZING raffle donation that will be up for grabs at the raffle table!🤍

Sign up for the fun at the link below or in our bio!
🔗 https://runsignup.com/Race/MA/EastOtis/SmileLikeJack taken in Otis Reservoir by @smilelikejack

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3 months ago

We are just 6️⃣ days away from race day!! Are you ready?!🏃🏻‍♀️🏃‍♂️🏃🏽

Join us for a fun filled race day with amazing raffle prizes, incredible JWO merch honoring Jack, coffee from Fiore Cafè, food/drinks from the Knox Trail Inn & even better company! 🎟️🤍☕️

🚨Sign up for the fun at the link in our bio or below today!!
🔗 https://runsignup.com/Race/MA/EastOtis/SmileLikeJack taken in The Berkshires by @smilelikejack

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3 months ago

HAPPY 4TH OF JULY🧨🩵

The countdown is on! 🗓️

We are officially ONE week away from the 2026 Smile Like Jack 5k/10k/Family Fun Run!! 🏃🏻‍♀️🏃🏽🏃‍♂️

Join us for a fun filled day honoring Jack!🩵

Sign up at the link in our bio or below today!!
🔗 https://runsignup.com/Race/MA/EastOtis/SmileLikeJack taken in KNOX TRAIL INN by @smilelikejack

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3 months ago

We are just about 1️⃣ week away from race day!

We can’t wait to see you there! 🏃‍♀️ Sign up for the race at the link in our bio or below!

🔗 https://runsignup.com/Race/MA/EastOtis/SmileLikeJack taken in Otis Reservoir by @smilelikejack

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3 months ago

🎟️RAFFLE UPDATE🎟️

Thank you to Coastal Bridge Advisors ( @coastal_bridge_advisors )for this super amazing raffle donation of the RayBan Meta sunglasses!! 🕶️

Want a chance to win this awesome prize? Come hang at the Smile Like Jack road race on July 11th!! 🏃‍♂️🏃🏽🏃🏻‍♀️ Sign up at the link in our bio or below!!

🔗https://runsignup.com/Race/MA/EastOtis/SmileLikeJack taken in KNOX TRAIL INN by @smilelikejack

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4 months ago