
Entertainment
Why contact us?
Entertainment can make or break an event, and we live in that world every day. From large-scale fundraisers and corporate events to theatrical musicals and packed pub nights, we’ve been a part of or handled it all. We know the players, we know the pitfalls, and we know how to maintain professionalism while making it feel effortless. Think of us as the one-stop shop you didn’t know you needed...good vibes, shared moments, and results that last long after the lights go out.
Our client list includes but is not limited to: Cape Breton University, The Savoy Theatre, the Cape Breton Miners Museum, Membertou Trade and Convention Centre, United Way Cape Breton, The Men of the Deeps, The Cove Guest Home, Sydney Credit Union, St.FX University, the CB Highlanders Association, The IWK Tailgate Race Weekend, Inverary Inn, Meco Construction, Big Pond Community Hall.
Productions under OSE's creation (or co-creation) and direction: Cape Breton's Island Girls, The Legends Tribute Series, Vinyl33 Tribute Series, The Lamplight Gala, Happy Ha Ha Holidaze Music & Comedy Show, Yours Truly Cape Breton, The Cape Breton Christmas Hour (online show), Garbage Night Sessions (online show).
We have also provided our services for numerous celebrations and fundraisers, including The Men of the Deeps' 50th Anniversary, The Savoy Theatre's 50th Anniversary, Hospice Palliative Care fundraisers, the Fiona Relief Concert, and the Cape Breton Music Hall of Fame Show (year one), among others.
If you're having an event and need entertainment but have no idea where to begin, give us a call.
We'll start, as we always do in Cape Breton, with a quick chat...

Live Music Event
Design and Production
Olive Street Entertainment has been shaping stages since 2010. Fundraisers, corporate functions, weddings, and big nights all rise or fall on the strength of their entertainment. We make sure it’s the part people remember for the right reasons. Over the years, we’ve built trusted relationships with remarkable artists, some of the best stage and studio musicians on the East Coast, as well as many venue managers and technical specialists. When the project calls for more, we know who to call: producers, agents, venues and crews who share our standard for getting it right.

Voice and Media Production
Our partners bring years of experience in radio, television, ad writing, and design, with enough time in the field to know how to make words carry weight. Voice-overs, narration, jingles, audio and video pieces…it’s all part of the toolkit. From small touches to full-scale production, we know how to scale it and who to call when it needs more.
High Energy, High Quality
Party Bands for any Occasion
For over 15 years, High Society and The Privateers have been packing dance floors and helping to create unforgettable events across Cape Breton and Atlantic Canada. More than just music, this crew of nine performers make it their mission to lift the room, bring the energy, the engagement and turn every gathering into a party. Their set-lists are extensive and cover a wide range of styles with Classic Rock, Celtic rock, Country, Pop, Folk, Cape Breton songwriters and beyond. Operated by Olive Street Entertainment, these groups, which often play as one, feature keys, drums, guitars, mandolins, horns, bass, fiddle and seven vocalists. They are supported by dependable crews who ensure every detail runs smoothly. So if you’re ready for a night where the only complaint is sore feet, we know just the bands to call.

