Join us on Saturday, May 1st, 2021 from 4pm-9:30pm

at Boston College High School 

for our First Annual Kentucky Derby Gala!

Please click here to purchase tickets!

Sponsorship opportunities are available NOW!
Call Casey Cunningham at 774-222-3421 for information.
We hope to see YOU at the Kentucky Derby!



ALL children deserve the same opportunity to have great memories of  their own.


note from Jen Cunningham

The goal of the Rob Cunningham Foundation's Kentucky Derby Gala is to raise funds to assist children in Massachusetts by helping provide the “extras” for the next generation and help children reach their full potential.  All proceeds will assist in funding extracurricular activities to allow children to grow and learn.

Many families are unable to send their children to after school programs, sports, band or summer enrichment programs.


In an age when music and art programs are sometimes cut by school boards, sports programs and gear are more expensive than ever, and art supplies cost an arm and a leg… It’s not easy to keep up.

Imagine how we could better the lives of children all across our Commonwealth by providing them with amazing opportunities of extracurricular activities!

Take a minute to remember the things you did as a child. Did you go to summer camp? Did you play an instrument or a sport? Did you take art lessons or attend enrichment classes?

This year, in addition to scholarships and the endowment in Rob’s name at BC High, the Foundation has decided to work with schools, camps, and different enrichment programs all across Massachusetts to give underprivileged children in our communities the opportunity to discover the best in themselves through extra-curricular activities, which will foster growth and opportunity while encouraging independence and FUN!

In May, we will be throwing The First Annual Rob Cunningham Foundation Kentucky Derby Gala at Rob's Alma Mater Boston College High School to raise the funds needed to provide the children in our Commonwealth with opportunities to enrich their lives and their futures.​ In order to do this, we need to expand our reach! With your help, we know we can better the world and help kids find their paths; whether it’s the science camp that will help them discover the next planet, the voice lessons that will help them become the next Elton John, or the art supplies that helps them become a modern day Davinci, we want to help! For some, having these extras can make all the difference and give them the tools and guidance to bring them to where they want to be.


I hope you will all join us on May 1st, 2021 from 4-9:30PM for this fun event! It won't be your average gala! Crazy bowties and silly hats are encouraged!  We couldn’t do the things we do in service of others if it weren’t for the generosity of people like you. I am humbled to have so many great friends and family, and hope to see you at the Derby!