Fundraising Events
Join us at our upcoming events and support the SHSB Charitable Trust
SHSB Big Bike Ride
| Friday 10th July 2026 | |
| Southend High School for Boys, Prittlewell Chase, Westcliff-on-Sea, SS0 0RG |
The School will run a Big Bike Ride this summer in aid of the SHSB Charitable Trust... More details on how to get involved and show your support will be shared in due course.
OSA Festival of Music
| Friday 10th July 2026 | |
| The Boundary, Garon Park, Southend-on-Sea, SS2 4FA |
Following the success of the 2025 Summer Dinner Dance, The Old Southendian Association is pleased to share the date of this year's Festival of Music, featuring SHSB Big Band musicians past and present. This once again promises to be a spectacular show with talented instrumentalists and singers.
Booking is now open, with tickets available from £25, or £40 seated. Food will be served from our delicious pop-up stalls (available to buy on the night). Email tickets@oldsouthendianassociation.org to reserve your place and avoid disappointment!
Past events from 2025
Summer Dinner Dance
| Friday 11th July 2025 | |
| 6:30 PM for 7 PM | |
| The Boundary, Garon Park, Southend-on-Sea, SS2 4FA |
Thank you to everyone who joined The Old Southendian Association and raised over £13,000 for the Southend High School For Boys Charitable Trust!
It was an unforgettable evening of food, music and dancing at The Boundary, Garon Park with fantastic entertainment provided by the school's renowned Big Band and the Old Boys Band, featuring mix of current students and talented alumni.
SHSB Charity Walk 2025
| Friday 18th July 2025 |
The School ran its annual Charity Walk this summer in aid of the SHSB Charitable Trust... All told, over £12,700 was raised. Thank you to all involved for your support and generosity!
A Musical Marathon
| Saturday 6th December 2025 | |
| 9 AM to 9 PM "around the clock" | |
| Southend High School for Boys, Prittlewell Chase, Westcliff-on-Sea, SS0 0RG and online |
Thank you to everyone who performed at or attended the epic Musical Marathon where 12 hours of non-stop celebration brought together current and past school members, alongside guests, friends and family, with an audience in the hall and beyond via the livestream.
The exceptional music-making entertained us with everything from classical piano to jazz bands, rock, Christmas songs and singalongs, choral music, organ, bands, ukuleles, songs from the stage and screen, and more!
Merry ChristMoose!
| Order before Thursday 10th December 2025 | |
| Collect from Southend High School for Boys, Prittlewell Chase, Westcliff-on-Sea, SS0 0RG |
We were excited to share the school's new Christmas range depicting the famous Moose that holds pride of place in the dining hall.
The range included Christmas cards, wrapping paper and Christmas baubles!
All proceeds go to the school to better support our students now and in the future.
To read about the story behind the moose, see this article from the Old Southendian Association's 2009 Magazine.
SHSB Charity Walk 2025
| Friday 18th July 2025 | |
| 6 PM to 8 PM | |
| Southend High School for Boys, Prittlewell Chase, Westcliff-on-Sea, SS0 0RG |
Further information will be shared on the launch event for the Charitable Trust in due course.
In the meantime, please contact us to register your interest.