Smyly Sickwitit Ignites the 49th Annual Roslindale Parade
- jeramieregis
- Oct 11
- 2 min read
Smyly Sickwitit Ignites the 49th Annual Roslindale Parade
On October 5th, 2025, the streets of Roslindale came alive — not just with music and movement, but with heart, pride, and history. As the 49th Annual Roslindale Parade rolled through the neighborhood, one familiar sound rose above the rest: the voice and energy of Smyly Sickwitit, Roslindale’s own son and a true hometown hero.
For over 13 years, Smyly has performed at this cherished community event. But this year felt different — deeper. Smyly's theme honored the legacy of Roslindale High School, a symbol of unity, growth, and hometown pride. As Smyly’s float rolled down the avenue, people didn’t just watch — they danced, they sang, and they celebrated together. From the streets to the rooftops, the crowd was FLOODED with love.
A Tribute to Roots and Resilience
Born and raised right here in Roslindale, MA. Smyly Sickwitit isn’t just an artist — he’s a reflection of the community that raised him. His journey from local talent to recognized performer is proof that greatness often begins right at home. Every lyric, every smile, every wave from that float carried the spirit of Roslindale — loyalty, hard work, and love for his people. This wasn’t just entertainment; it was a living lesson in gratitude and growth.
The Power of Tradition and Togetherness
For nearly five decades, the Roslindale Parade has been a stage for memories — a time when generations come together to celebrate community and culture. And year after year, Smyly has helped keep that rhythm alive. As families waved flags, kids danced beside the floats, and elders smiled with pride, one truth stood out: tradition stays alive when love fuels it. Music isn’t just sound — it’s connection. It’s emotion. It’s legacy.
An Inspiration for the Next Generation
For the young dreamers watching from the sidelines — those with microphones, paintbrushes, cameras, and visions — Smyly’s story says: you can grow big and still keep your roots strong.
“Never forget where you come from — your foundation is your forever.”
Being FLOODED isn’t only about success; it’s about being blessed with purpose, driven by community, and grounded by gratitude.
Roslindale Forever ❤️❤️❤️
When the music faded and the floats moved on, one thing lingered in the air — pride. Pride in Roslindale. Pride in heritage. Pride in one of their own who keeps coming home to lift spirits and inspire hearts.
A post by @fosterrs on Instagram stated “Simply the happiest dude at the #Roslindale Day Parade was this dancing fellow following @smylysickwitit”. The 49th Annual Roslindale Parade wasn’t just another event — it was proof that when art, love, and community come together, the result is timeless.
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