Kelowna Events October 2026 | Railside Brewing

Kelowna Events This October 2026 | What’s Happening at Railside!

Kelowna Events This October 2026 | What’s Happening at Railside

We’re working on events to ring in the official start of the ‘BER months! Check back!

These are the events taking place at Railside this October!

Railside Brewing – October Event Schedule – See below for full details and tickets!

Every Monday | 8–10 PM

Karaoke Mondays Hosted by Kelowna Rock Choir
Our weekly karaoke night continues all month long. We want to hear you sing whether you’re a seasoned performer or just there to cheer on your friends, everyone is welcome.

Every Thursday | 6:30–9 PM

Off the Rails Trivia
Gather your smartest teammates and put your knowledge to the test during our weekly trivia night.

Every Saturday | 7–9 PM

Trivingo
Our popular mashup of music trivia and bingo returns every Saturday night.

October’s Special Events

See below for more details!

October 3 – Ride for Refuge + Lunch + Jeff Hansen
October 3 – Sunset Sessions – Four DJs – No Music Trivingo
October 12 – Closed Early for Thanksgiving (7pm – No Karaoke!)
October 14 – Fall Vintage Market
October 20 – Fall Paint Night
October 25 – All-Ages Pumpkin Carving
October 26 – A Court of Thorns and Roses Midnight Book Launch – Sold Out
October 28 – Halloween Drag Bingo
October 31 – Halloween Party – The ’90s is calling (on the landline)!

November 1 – Cut for a Cause! Rob’s big Halloween hair cut!

Live Music Lineup

October Live Music at Railside

See the Full October Live Music lineup here!

Kelowna Things to Do: Railside October Events Calendar

Explore Railside’s October events schedule!

FRIDAY NIGHT LIVE MUSIC

Check out this month’s lineup!

live music on friday nights in kelowna at railside brewing

OCTOBER LIVE MUSIC SCHEDULE!

Friday, October 2nd – Jon Fennell

Jon Fennell kicks off October’s live music lineup at Railside. Grab a pint, find a spot and start the first weekend of the month with live local music at the brewery.

Sunday, October 4th – Of Candor

2:00–4:00 PM

Of Candor takes over our Sunday afternoon live music session. Stop by from 2:00–4:00 PM for an easy-going afternoon of live music, good food and a few beers.

Friday, October 9th – Annarose

Country Rock

Annarose is back at Railside with her country rock sound. If you caught her in September, you know she’s a great fit for a Friday night at the brewery.

Sunday, October 11th – Joshua Smith

Singer-Songwriter | 2:00–4:00 PM

Joshua Smith returns for another Sunday afternoon performance. Settle in with a pint and enjoy his singer-songwriter set from 2:00–4:00 PM.

Friday, October 16th – Timmy Rhyno Trio

The Timmy Rhyno Trio joins us for Friday night live music in the middle of the month. Get your weekend started at Railside with live music, cold beer and a night out with friends.

Sunday, October 18th – Siren & Scribe

2:00–4:00 PM

Siren & Scribe make their October appearance for our Sunday afternoon music series. Join us from 2:00–4:00 PM for a relaxed afternoon at the brewery.

Friday, October 23rd – River of Kings

Rock

River of Kings returns to Railside with another Friday night of rock. Grab your crew, order a pint and settle in for live music as we head into the final weekend stretch of October.

Sunday, October 25th – James Hay

2:00–4:00 PM

Join us from 2:00–4:00 PM for a relaxed afternoon at the brewery.

Friday, October 30th – Sammy Cooper

Indie Rock

Sammy Cooper closes out October’s live music lineup on the night before Halloween. Join us for indie rock, cold beer and one last Friday night performance for the month.

Ride for Refuge

Saturday, October 3 | Ride/Walk Starts at 10:00 AM | Lunch 11:30 AM–1:00 PM | Live Music 12:00–2:00 PM

Railside is the starting and finishing point for this year’s Ride for Refuge, with participants heading out for a bike ride or walk beginning at 10:00 AM.

Afterwards, stick around for a hot dog lunch from 11:30 AM–1:00 PM and live music from Jeff Hansen from 12:00–2:00 PM.

It’s a great opportunity to get outside, take part in a community event and finish things off back at Railside with lunch and live music! See you all here!

Sunset Sessions

Saturday, October 3 | 7:00 PM–12:00 AM | Free Admission

Saturday keeps going with Sunset Sessions taking over Railside from 7:00 PM until midnight.

Four DJs are lined up for the evening, and there’s no cover, so come down, grab a beer and spend Saturday night with us.

Please note: There will be no Music Trivingo on October 3rd.

vintage market railside brewing october 2026

Fall Vintage Market

Wednesday, October 14 | 4:00–8:00 PM

Vintage shopping is back at Railside this October!

Stop by between 4:00 and 8:00 PM to browse the Fall Vintage Market while enjoying a beer at the brewery. It’s an easy midweek excuse to get together with a friend and see what you can find.

More market details are coming soon, so stay tuned to our website and socials!

pumpkin-carving-railside-brewing-kelowna-october-2026

Pumpkin Carving at Railside

Sunday, October 25 | 3:00–7:00 PM | $15 | All Ages

Halloween is getting closer, which means it’s time to carve some pumpkins!

Join us at Railside for an all-ages afternoon of pumpkin carving. Your $15 registration includes a pumpkin and carving kit, so we’ll have the essentials ready for you.

Bring the family, get creative and leave with a jack-o’-lantern ready for Halloween.

october-midnight-book-release-railside-brewing-kelowna-2026

A Court of Thorns and Roses Midnight Book Launch

Monday, October 26 | 9:30 PM–12:00 AM | SOLD OUT

Railside is hosting a special A Court of Thorns and Roses Midnight Book Launch on October 26.

The ticketed event sold out shortly after tickets were released, so Railside will close to the general public at 9:00 PM that evening rather than the usual 10:00 PM closing time.

If you’ve already got a ticket, we’ll see you there!

Halloween Drag Bingo

Wednesday, October 28 | 8:00 PM | 19+

Drag Bingo is getting a Halloween makeover!

Join us for a spooky edition of one of Railside’s favourite monthly events, with all the usual Drag Bingo fun plus a Halloween theme for October.

This is a 19+ event beginning at 8:00 PM.

Halloween at Railside! ’90s Party with Bush Party!

Saturday, October 31, 2026 | 8:00–11:00 PM | No Cover

Halloween is going old school at Railside Brewing this year! We’re throwing it back to everyone’s collective favourite decade, the ’90s with Bush Party! The ’90s rock cover band that’s rocked the brewery before, returning for a Halloween night full of familiar hits, throwback fashion and plenty of nostalgia.

Dig out your flannel shirts, throw on some dickies, windbreakers and docs, or come dressed as your favourite 90s movie, TV or music character. Whether you’re channelling Kurt Cobain, a Spice Girl or someone straight out of Clueless, we want to see your best ’90s look!

And speaking of costumes, Rob has been growing out his hair for months to achieve what he’s calling his ultimate “dirtbag” look. His actual Halloween costume is still a closely guarded secret, so you’ll have to come down to see what all that hair has been leading up to!

Here’s what’s happening:

Live Music: Bush Party performing 90s rock favourites from 8:00–11:00 PM
Costume Prizes: Prizes for the best-dressed guests
Specialty Cocktails: Halloween drinks to keep the party going
No Cover: Free admission all night

One More Thing! Rob’s Hair Is Coming Off!

Rob’s Halloween transformation doesn’t end when the party does. On Sunday, November 1, we’re hosting Cut for the Cause, a fundraiser supporting JoeAnna’s House.

For a minimum $10 donation, you can enter for a chance to be the lucky person who gets to buzz off Rob’s hair! Registration starts at 3:00 PM, with the big draw and haircut at 4:00 PM.

So come celebrate Halloween with us, see Rob’s mystery costume in all its glory, and return Sunday to watch him say goodbye to those luscious locks for a great local cause.

October 31st at Railside Brewing. Let’s party like it’s 1990- something!

cut for a cause joeannas house kgh fundraiser

Cut for a Cause at Railside Brewing!

Rob’s Big Halloween Haircut!

Sunday, November 1, 2026 | Registration at 3:00 PM | The Big Buzz at 4:00 PM

If you’ve noticed Rob sporting a little more hair than usual lately, there’s a reason for it! He’s been growing it out for a top-secret costume for Railside’s big ’90s Halloween Party with Bush Party. But once Halloween is over, those locks are coming off for a great cause.

On Sunday, November 1, Railside is hosting Cut for a Cause, a community fundraiser supporting JoeAnna’s House.

And here’s the fun part: you could be the one holding the clippers!

How to Get Involved

Registration: Begins at 3:00 PM
The Big Draw: 4:00 PM, when one lucky winner is selected to shave Rob’s head
Minimum Donation: $10 per entry
All Proceeds: Supporting JoeAnna’s House

Want to support the fundraiser but can’t make it on Sunday? Donations are being accepted at Railside ahead of the event, so you can still contribute even if you can’t be there for the big haircut.

Want to Join the Buzz?

Rob isn’t the only one getting a haircut!

If you’re ready to part with your own locks for a good cause, Railside is inviting others to join the fundraiser and get involved.

Interested in participating? Contact events@railsidebrewing.ca for more information.

Come Watch the Transformation!

First, catch Rob’s mystery costume at our ’90s Halloween Party on October 31st. Then come back Sunday afternoon to see the before-and-after transformation!

Whether you’re entering for a chance to wield the clippers, volunteering for your own haircut or just stopping by to support the cause, it’s a fun way to help make a difference for a local organization.

Come for the big buzz and help us raise money for JoeAnna’s House!

THE O.G’s!

Join us at Railside Brewing for some consistently solid fun!

THURSDAY NIGHT TRIVIA

Every Thursday starting at 6:30 pm!

TRIVIA NIGHT IN KELOWNA!

Join us at the Brewery, for the Best Trivia night in Kelowna, every Thursday!

The most popular Trivia Night in Kelowna continues this Fall at Railside! Hosted by Matt, you’re always guaranteed at least one or two laughs, even if you don’t learn something new. 3 rounds of questions and 1 round of “Name that tune & artist”; the questions and categories are always changing and always sure to entertain!

Tiebreaker challenges include dance-offs, pictionary, and more because we all know – there are no ties allowed at Railside.

Bragging rights are on the line when the questions start at 6:30pm! Be sure to call ahead and book a table for your crew in advance because this is a busy one around here!

LEARN MORE!

FRIDAY NIGHT LIVE MUSIC

Every Friday!

LIVE MUSIC IN KELOWNA!

Join us at the Railside, for the Best Live Music in Kelowna, every Friday!

Kick off your weekend with live music every Friday at Railside, starting at 7 pm. Enjoy a rotating lineup of talented local and touring musicians, great beers, and a relaxed, welcoming atmosphere.

Live music happens every Friday unless otherwise noted, so be sure to check the schedule for specific dates, performers, and any special timing updates.

Grab a seat, a pint, and settle in for a great night of live music at Railside!

LEARN MORE!

SATURDAY TRIVINGO!

Not quite Trivia, not quite BINGO! – Join us to find out!

saturday night kelowna events music trivia with bonnie at railside brewing

MUSIC + BINGO + TRIVIA IN KELOWNA!?

Music Trivingo – Every Saturday Night at Railside!
7–9 PM | No Cover | Hosted by Bonnie
Not Quite Bingo, Not Quite Trivia – All Fun

Get ready to sing, dance, and dab your way through Music Trivingo! Railside Brewing’s new Saturday night ritual! Hosted by the one and only Bonnie, this high-energy mashup of music trivia and bingo will have you guessing songs, hitting the dance floor, and laughing all night long.

We provide the dabbers, you bring the good vibes.
No cover charge, just great beer, great tunes, and a guaranteed good time.

Every Saturday from 7–9 PM—come make it your new weekly tradition!

LEARN MORE!

MONDAY KARAOKE!

Warm up the pipes for Railside Idol!

You asked, so we’re going to deliver!

Every Monday at Railside, hosted by Kelowna Rock Choir

Karaoke is here every Monday night! Dust off your pipes and practice your best rendition of “I Want It That Way” because stage fright ain’t pretty!

Join us for a lively evening of rock ballads and whatever else tickles your fancy!

Kelowna Events This October 2026 | What’s Happening at Railside!

Kelowna Events This October 2026 | What’s Happening at Railside

Railside Brewing – October Event Schedule – See below for full details and tickets!

Every Monday | 8–10 PM

Every Thursday | 6:30–9 PM

Every Saturday | 7–9 PM

October’s Special Events

Live Music Lineup

October Live Music at Railside

Kelowna Things to Do: Railside October Events Calendar

FRIDAY NIGHT LIVE MUSIC

Friday, October 2nd – Jon Fennell

Sunday, October 4th – Of Candor

Friday, October 9th – Annarose

Sunday, October 11th – Joshua Smith

Friday, October 16th – Timmy Rhyno Trio

Sunday, October 18th – Siren & Scribe

Friday, October 23rd – River of Kings

Sunday, October 25th – James Hay

Friday, October 30th – Sammy Cooper

Ride for Refuge

Sunset Sessions

Fall Vintage Market

Pumpkin Carving at Railside

A Court of Thorns and Roses Midnight Book Launch

Halloween Drag Bingo

Halloween at Railside! ’90s Party with Bush Party!

One More Thing! Rob’s Hair Is Coming Off!

Cut for a Cause at Railside Brewing!

Rob’s Big Halloween Haircut!

How to Get Involved

Want to Join the Buzz?

Come Watch the Transformation!

THE O.G’s!

THURSDAY NIGHT TRIVIA

TRIVIA NIGHT IN KELOWNA!

Join us at the Brewery, for the Best Trivia night in Kelowna, every Thursday!

FRIDAY NIGHT LIVE MUSIC

LIVE MUSIC IN KELOWNA!

Join us at the Railside, for the Best Live Music in Kelowna, every Friday!

SATURDAY TRIVINGO!

MUSIC + BINGO + TRIVIA IN KELOWNA!?

MONDAY KARAOKE!

You asked, so we’re going to deliver!

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