Representing the 905: Keysha Freshh Brings Hip Hop Home to Convergence
- Ashley Marshall
- Aug 14
- 4 min read
Welcome to the 905! Friday, September 19, marks the kick-off of Oshawa’s annual Convergence Music and Art Festival, a celebration of local talent, arts, vendors, culture, community, and unforgettable performances. From 1 to 9 p.m., Black and Indigenous culture takes center stage with drum circles, beatboxing, emcees, and DJs filling the air with rhythm and energy. In partnership with RISE Edutainment and Hip Hop ‘Til Infinity, Tourism Oshawa and Durham’s DEI department have curated a program designed not only to represent these vibrant voices, but to amplify them—sparking collaboration, recognition, and lasting connections.
Making an appearance on the Cosmic Main Stage is Keysha Freshh, a rapper with over 20 years of experience who earned her name from the legendary Doug E. Fresh, one of hip hop’s true pioneers. Growing up in Durham, I remember listening to local icons like Choclair, Maestro Fresh Wes, and Kardinal Offishall. It took many more years before I discovered the women commanding the scene—artists like Michie Mee, Haviah Mighty, and, of course, Keysha Freshh. As hip hop celebrates its 51st birthday, it remains one of the youngest genres of music—a style, a culture, and a message that continues to evolve, reinvent itself, and challenge the status quo.
Hip hop culture and rap music are in good hands with Keysha Freshh, who is bringing her talent to the festival. I had the pleasure of meeting with Keysha to learn what it means to represent the 905 at such a pivotal moment in hip hop’s legacy. “I want to represent and speak for the people of Oshawa, and that’s really important to me.” Keysha Freshh is the recipient of the 2025 Culture Counts Professional Artist Award, presented by the City of Oshawa. This award recognizes Keysha’s “outstanding creativity, originality, professional maturity, and leadership in the arts community.” She was bestowed the same honour by the City of Ajax in 2022.
As a Black girl growing up in Durham, I could relate to the very familiar experience of not seeing many of us represented, let alone the diversity of our cultures being given space to be expressed. Having Jamaican roots, I always gravitate to hip hop that has heavy reggae influences; The Fugees come to mind (The Miseducation of Lauryn Hill was named the greatest album of all time by Apple Music). The influences of reggae, Brooklyn’s iconic “boom bap” drum pattern, the “chopped and screwed” style originating from Texas, or the laid-back cruisin’ tempo of LA’s rap scene, all play a part in how Keysha Freshh approaches her music, most notably in her hit “No Long Talking.” Keysha infuses her own Guyanese roots into her soulful sound, blending genres and bending boundaries. There is something both familiar and unexpected in her delivery, a masterful skill that is indicative of rap music. Keysha and I agreed that an artist with such range performing at a street festival is a big deal. Making this music accessible to everyone, with such important torch bearers at the helm, adds so much flavour and richness to the city, and gives people in the community something truly galvanizing.
I remember going all the way to Toronto to seek the underground hip hop scene, witness cyphers, and be in the audience when rappers and poets were trying out new material. I was blown away when I first saw R.I.S.E. (Reaching Intelligent Souls Everywhere) featured in Nuit Blanche, its first expansion into Scarborough, curated by Alyssa Fearon. R.I.S.E. came out for Convergence last year, and they are coming again this year, in an even bigger and more impactful way. Excited by the involvement of Tanika iNsight Circles, Keysha was poised to say yes to such an opportunity. Especially after her 12+ years of supporting R.I.S.E. and being a mentor to emerging artists, Keysha Freshh is committed to community and to her craft.
I asked Keysha what she was most excited about for her upcoming performance. “My peoples coming out to see me.” She explained that, given her touring schedule, it is rare that her friends and family can see her perform. There is something truly special about being shown some hometown love, seeing the faces of your loved ones in the audience, and being able to give back to the city that has supported you. As an artist, this is what excites Keysha Freshh about being able to perform in Oshawa.
While Oshawa’s Convergence Festival attracts talent from artists who have been nominated for Junos, who have been backup singers to Grammy Award-winning artists like Alicia Keys, and who are just starting to cut their teeth in front of a live audience, there is room for artists of all stages to be seen, heard, and celebrated.
The party doesn’t stop there! There is an entire lineup of afterparties for the festival, further showcasing local acts that have made it big. I am most excited to see K-os take to the BOND|ST stage and give us classics from his discography. Getting his start in Whitby, the music of K-os is a taste of home that complements the deliberate invitation of artists from around the Durham Region. As a soundtrack to my youth, his music has staying power, blending rap and hip hop with alternative, funk, and drum and bass.
Join us on September 19 for day one of the Convergence Music and Art Festival in downtown Oshawa. Then, on September 20, the celebration continues with three live music stages, immersive art experiences, and more, filling the streets with energy and creativity. Convergence is all about great food, amazing people, and those magical moments when you cross paths with world-class talent.