Smile Like Jack Memorial Fund

Smile Like Jack Memorial Fund In honor of Jack William O’Brien, the Smile Like Jack Memorial Fund has been established to honor his legacy as an avid outdoorsman.

We are less than ONE MONTH away from race day!!🥳Sign up TODAY to join the fun on July 11, 2026. There will be raffle pri...
06/12/2026

We are less than ONE MONTH away from race day!!🥳

Sign up TODAY to join the fun on July 11, 2026. There will be raffle prizes, never before seen JWO merch, food, beverages, music & good company!!🩵🏃🏻‍♀️

Kickoff the Otis Reservoir fireworks weekend the right way at the 5th annual Smile Like Jack Memorial Fund road race! We want to see you there!!

Sign up using the 🔗 link below or in our bio!
https://runsignup.com/Race/MA/EastOtis/SmileLikeJack

🎟️RAFFLE UPDATE🎟️Thank you to Barb Rogers, Ken Rogers, and Jared Roger’s as well as Mackenzie and Dylan Radacsi for thei...
06/09/2026

🎟️RAFFLE UPDATE🎟️

Thank you to Barb Rogers, Ken Rogers, and Jared Roger’s as well as Mackenzie and Dylan Radacsi for their amazing donation of the Beats Solo 4! 🩵🎧 we are SO grateful for this generous donation!

This is just one of the amazing raffle prizes that have been donated for race day! And we are still accepting raffle donations!🤍Sign up for the Smile Like Jack road race today to join the fun!

Sign up at the 🔗link in our bio or below today!
https://runsignup.com/Race/MA/EastOtis/SmileLikeJack

06/07/2026

The Smile Like Jack Memorial Fund Scholarship is awarded to students who lead with kindness, lift up those around them, and make their communities better simply by being themselves.

This year, we are proud to recognize Joey Abderhalden, Emma Ranzoni, Will Mairo, Ryder Drenga, and Adam Pincelli of Lee High School as scholarship recipients. 🎓

Each of these young men and women has demonstrated the character, heart, and determination that Jack carried with him every day. Whether through their friendships, leadership, work ethic, or willingness to help others, they represent the values that continue to inspire the mission of Smile Like Jack.

Congratulations, Joey, Emma, Will, Ryder, and Adam. We are honored to celebrate your accomplishments and look forward to seeing all the great things your future holds!

Congratulations to Cole Kennedy, Mason Buffoni, Andrea Paul, Frankie Bilotta, Tyler Campbell, and Larkin Howard! These 6...
06/05/2026

Congratulations to Cole Kennedy, Mason Buffoni, Andrea Paul, Frankie Bilotta, Tyler Campbell, and Larkin Howard! These 6 Monument Mountain students are the recipients of the 2026 Smile Like Jack Memorial Fund scholarship. 👩🏻‍🎓👨🏼‍🎓🎓

Each of these outstanding students embodies qualities that made Jack so special. Through their kindness, compassion, positive attitude, determination, and willingness to help others, they reflect the values Jack carried with him every day. Whether through their leadership, friendships, community involvement, or the way they treat those around them, these students have demonstrated the character and spirit that this scholarship was created to honor.

We are proud to recognize Cole, Mason, Andrea, Frankie, Tyler, and Larkin for their achievements and for carrying forward the legacy of making a difference in the lives of others - just as Jack did.

Congratulations to all of this year’s recipients.

Smile Like Jack is honored to sponsor the Danny Dollar Event at Lee Elementary School for the third consecutive year. Th...
06/04/2026

Smile Like Jack is honored to sponsor the Danny Dollar Event at Lee Elementary School for the third consecutive year. This special event celebrates teaching financial literacy and the power of making a positive impact and values that were at the heart of who Jack was. We are proud to continue supporting an event that encourages students to lead with hard work and dedication

06/02/2026

🎟️We officially have a winner!!🎟️

Congratulations to James Jacquier on winning the FREE raffle pack! 🏆Come race day let us know at registration that you were the winner & we’ll give you your free raffle pack!

Please reach out within 48 hours to accept your prize!

‼️At this time, all registrations will no longer come with a race t-shirt upon sign up‼️

🚨We are still accepting sponsors, but if you sign up to be a platinum sponsor, you will not receive a shirt upon race sign up.

Regardless of having a shirt or not, there will be plenty of amazing merchandise available to you on race day! 🤍Come join the fun!

🔗Register up until July 11th at the link in bio or using the link below! We can’t wait to see you there! 🏃🏽🏃🏻‍♀️🏃‍♂️

https://runsignup.com/Race/MA/EastOtis/SmileLikeJack

🎟️RAFFLE UPDATE🎟️Another day another raffle update!!Thank you to Bella Med Spa for your generous donation of 1 syringe o...
05/31/2026

🎟️RAFFLE UPDATE🎟️

Another day another raffle update!!

Thank you to Bella Med Spa for your generous donation of 1 syringe of dermal filler & 2C units of tox !!🧖🏻‍♀️💉

‼️ There are TWO more days to sign up for the race and be entered into a drawing to win a FREE raffle pack!! The winner will be drawn on June 2nd!!

Additionally, don’t forget to sign up before June 1st at 11:59pm EST to make sure you receive your complimentary race day shirt!!

🔗 Sign up for the 2026 Smile Like Jack race at the link below or in our bio‼️
https://runsignup.com/Race/MA/EastOtis/SmileLikeJack

🎟️RAFFLE ALERT🎟️Thank you to Bella J’s Salon for donating these amazing hair care goodies! 🧖🏻‍♀️🫧There’s only 3️⃣ days l...
05/29/2026

🎟️RAFFLE ALERT🎟️

Thank you to Bella J’s Salon for donating these amazing hair care goodies! 🧖🏻‍♀️🫧

There’s only 3️⃣ days left to sign up for the race and receive a complimentary race-day shirt and be entered into a drawing to win a FREE raffle pack! (Raffle winner will be drawn on June 2nd)‼️

🔗 Sign up at the link below or in our bio today!! Don’t miss out!!
https://runsignup.com/Race/MA/EastOtis/SmileLikeJack

🎟️RAFFLE ALERT🎟️Check out this adorable wine basket, blanket and wine tasting for 4 at Balderdash! 🍷 This will be up for...
05/28/2026

🎟️RAFFLE ALERT🎟️

Check out this adorable wine basket, blanket and wine tasting for 4 at Balderdash! 🍷 This will be up for grabs at this year’s race raffle! We appreciate the donation so much!

Want a chance to win a FREE raffle pack? Sign up before June 1st at 11:59pm EST to be entered into the drawing!! As a friendly reminder, there’s also only 4 days left to sign up for the race and receive a complimentary race day shirt!

🔗Sign up at the link in our bio or below!
https://runsignup.com/Race/MA/EastOtis/SmileLikeJack

🎟️RAFFLE UPDATE🎟️Thank you to Sarah Ryan Talbot for donating this 55” Roku TV! We appreciate it SO very much!This is jus...
05/27/2026

🎟️RAFFLE UPDATE🎟️

Thank you to Sarah Ryan Talbot for donating this 55” Roku TV! We appreciate it SO very much!

This is just one of the many awesome prizes that have been donated so far! 🤍

🚨There’s less than one week to the t-shirt deadline!! Sign up for the race before June 1st at 11:59pm EST to be entered into the drawing for a FREE raffle pack and to receive a complimentary race day shirt upon sign up!🏃🏻‍♀️

Sign up at the 🔗 link in our bio or below!
https://runsignup.com/Race/MA/EastOtis/SmileLikeJack

Address

Westfield, MA
01086

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm

Telephone

+14134559199

Website

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