Oshawa in October: Where Culture, Concerts & Costumes Collide

Gotten over Convergence yet? Well most of those folks are still here in Oshawa, gathering, creating, crafting, entertaining. The venues are still here, the restaurants and comic stores are still here, The makers of culture are still here because Oshawa is a city of makers. It’s the DNA. So if you enjoyed that day well imagine a month of it, and here we go - October! It's Wowtober!  

Oshawa will be celebrating Hallowe’en which in this city is almost a civic holiday. The first annual Boo Bash happens in the downtown core along Celina Street on Saturday October 18 2025. Over 60 vendors, live music, Scare Zones, and treats. Bands playing include Vs The Borg, Night Chill, Fuzz Vultures, The Jasons, and Cybertronic Spree. It's all family friendly fun of course and the businesses along the street will all be in on the Boo!!

Don't miss Oshawa's Halloween Boo Bash, a family-friendly haunt filled with music, costumes, and thrilling surprises!

The actual Night of BOO! is of course on Oct 31 and folks can look forward to more scary fare on Hallowe’en night. The Biltmore Theatre has a presentation of the Rocky Horror Picture Show, the 50th anniversary of the cult hit released in 1975 on Saturday Oct 30 and Black Parade - an Emo Night celebration Friday Oct 31.

Bond St Event Centre has an All Hallow’s Eve Drag Show on Friday Oct 31 in the Main Stage and in the basement club TwoTwoTwo, formerly the Dungeon, local DJ Collective We Are Friends hosts their own Hallowe’en Party. 

Celebrate 50 Years of "The Rocky Horror Picture Show" at the Biltmore

While Hallowe’en is a really big deal in Oshawa there is some regular entertainment available during the months including a big time country show at the Tribute Communities Centre. Friday October 24 Canadian country stars Terri Clarke and Paul Brandt bring their Homecoming 2.0 tour to the city. 

The Biltmore Theatre roars into the month with Death From Above on Friday Oct 3 with support from Whitby rocker Chastity. More local talent gathers Sunday Oct 5 for the Hometown Sounds, an all day celebration of local music, food and art. Thursday Oct 9 indie rocker Daniel Romano Outfit makes a welcome return to the club and on Saturday October 18 another local gathering with Letdown, Nothing Serious, At This Point, and Live With it rocking the stage. Juno winner Maia Davies with Andy Stochansky conduct a more intimate gathering as they play the Mezzanine Stage Sunday October 19. Friday Oct 24 indie rockers Virginia To Vegas with Beyond the Sun play and on Sunday October 26 locally based trio Acoustic Blvd (Terry Crawford, Rick Johnson and Roger Watson) will play the room. They had previously played the intimate Mezzanine. The Biltmore also has a run of tribute acts throughout the month as does the Regent Theatre across the road.

The Biltmore Theatre lights up October 24 with Virginia to Vegas and Beyond the Sun.

Some of the acts performing at the Regent Theatre include Elton Sean, a tribute to Elton John, on Friday October 17; Hells Bells, a tribute to AC/DC Saturday Oct 18; Bonnie Rabson pays tribute to Dolly Parton and Reba McEntire Sunday, October 19 ; Ikons of Rock pay tribute to the classic rockers Thursday, October 23; Love Story, a tribute to Taylor Swift takes place Friday, October 24; and Saturday Oct 25 Tapestry pays tribute to one of the great singer/songwriters Carole King. 

Catch Elton Sean bringing all the hits of Elton John to the Regent Theatre on Friday, October 17.

Throughout the month there are also shows at the smaller bars and cafes such as Brew Wizards, Cork and Bean, the Atria, and at local record shop Kops Small Orbit plays Oct 4. 

So embrace the scare, lean into the night, enjoy the darkness, and trust Oshawa to find fun amongst all the fear.