How to Plan the Perfect Itinerary for RoadTrip Music Festival
By Sierra Saikaley
Published: August 27, 2026
This September, all roads lead to Kingston for the inaugural RoadTrip Music Festival happening Saturday, September 12th. And not gonna lie, I'm pretty pumped about it!
A mainstage concert featuring Peach Pit, Gabriel Jacoby, Katie Tupper and Kasador + a full-day music takeover of downtown's most exciting streets with a ton of free live music and unique vendors to discover. Say no more! I've got my tickets already!
But as with any new festival, it can be tough to figure out how to make the most of your time, so I've put together the only guide you need to plan the perfect day at RoadTrip Music Festival 2026
Step 1: Start Packing
Before we hit the road lets double check we've got everything we need for a comfortable day of music and fun!
RoadTrip Packing List:
- Tickets to the mainstage concert ✅
- A fire outfit ✅
- Comfy dancing shoes ✅
- Refillable water bottle ✅
- Hat and sunglasses ✅
- Debit/Credit Card and Cash ✅
- Portable Phone Charger ✅
- Earplugs ✅
- Your besties ✅
Plus, if you'd like to buy a refreshing Collective Arts brew from the licensed areas, make sure to bring a Photo ID!
10 AM: Coffee and Catch Ups
Gotta fuel up because this is an all-day festival and there's fun to have from 10 AM all the way to 11 PM!
100s of unique vendors and local shops are filling the streets with fun, and there are 3 free live music stages before the mainstage concert kicks off in the evening. There's so much to do; you need to start the day right!
☕ Every great road trip starts with caffeine! I'm meeting my friends on the BSE Skate Shop patio for Lemon Drops, then heading to Tommy's for some brekkie and day planning with the crew.
There are so many local cafe and dining options to choose from; you won't have any trouble finding a spot to fuel up!
Then it's time to start wandering down Princess St, taking in the endless fun at your own pace.
10 AM - 5 PM: Take the Scenic Route
Now that we've got a full tank, it's time to hit the road! No map, no problem, because we're taking the Scenic Route!
The Scenic Route Street Festival (10 AM to 5 PM) is bringing the most vibrant streets of downtown Kingston to life with all-day shopping, all-day dining and all-day fun!
Now is the perfect time to do some exploring before the music starts at 12 PM. We're checking out:
🛍️ 100s of Local Shops, Vendors & Fun Activations - The best local businesses in the city and incredible vendors are pulling out all the stops to fill Princess St. and the surrounding area with amazing open-air shopping, dining and activities!
I'm entering giveaways, I'm digging into free samples, I'm buying art, I'm spinning wheels, winning cool prizes, I'm high-fiving mascots and playing fun games with my friends. I'm doing it all, and so can you!
👕 Montreal St. Vintage Market | 10 AM to 5 PM - Montreal Street Collective, one of my favourite thrift shops, has invited 20+ vendors and artisans to transform Montreal St. into a vibrant vintage market.
🎁 Sydenham St. Mini Market | 10 AM to 5 PM - Sydenham St. Commons is the go-to chill-out spot downtown, and it has the cutest mini market with a curated mix of makers, artists, and small businesses.
🐶 Big Paws in the Basin | 10 AM to 3 PM - The Kingston Humane Society's 28th Annual Big Paws returns to Confederation Basin! Set against Kingston's waterfront, this event celebrates dogs and the people who love them!
Take your time while you're here. Browse the vendor booths, pop into a few shops, get your steps in and see what catches your eye. You never know what you'll discover on a road trip!
11 AM & 2 PM: Get Moving with Free Dance Classes
Let's get into the groove with free Hip-Hop and Line Dancing classes! Led by Jacob Vestervelt, these beginner-friendly classes will get you right into the RoadTrip spirit!
🕺Hip Hop Class | 11 AM - Feel the beat, loosen up, and throw down some fresh moves in the heart of downtown. Put your good shoes on, because this is just the beginning!
📍Outside STRONG Pilates Kingston - 259 Princess St
🤠 Line Dancing Lesson | 2 PM - It's boot scootin' time! Kick up your heels and stomp your way through some classic line dance steps, fresh off an amazing set by country music artist O Green.
📍Montreal St. Stage by The Caesar Company - 177 Princess St.
12 PM - 2:30 PM: Showtime! Last Call, Piner and Drag Storytime
It's showtime! The music is starting, and you've got a few ways to jump into the action.
🎶 Last Call | 12 PM - First up is Last Call, the winners of the RoadTrip x Queen's AMS Student Performer Contest. Their high-energy indie pop tunes are the best way to begin a day full of amazing live music.
🎶 Piner | 1:45 PM - Now it's time for beloved local singer-songwriter Piner to take the stage! Her music is intimate, raw and truly from the heart. Settle in, listen closely and stay awhile.
📍The Hub St. Stage by the Grizzly Grill - 395 Princess St
Or, if you're not ready for music just yet...
📖 Drag Storytime | 12 PM - Join BeeWitched, Kingston's witchy icon and beloved drag artist, for Drag Storytime. Fun stories, plenty of joy and a fabulous way to kick off the afternoon!
📍Brock St. by Martello on Brock - 66 Brock St
1 PM - 3:45 PM: Let's Get Country with O Green and Mariel Buckley
Country music fans, this is our time! Head to the Montreal St. Stage for an afternoon of country, folk, and a little bit of boot-scootin'
🎶 O Green | 1 PM - Bringing rich vocals and blue-collar storytelling to the stage, Tyendinaga's rising country star O Green is not to be missed. His music nods to the outlaw country tradition of the '60s and '70s, making his songs perfect for a sunny afternoon downtown.
🤠 Line Dancing Lesson | 2 PM - Jacob is back to put some boot-scootin boogie into today's schedule. Grab your friends and put your dancing shoes to work with this free line dancing lesson.
🎶 Mariel Buckley | 3 PM - Stick around for Juno Award-winning and Polaris Music Prize-nominated artist Mariel Buckley. Her unapologetically genuine, wry and soft-hearted take on alt-folk will make you smile, make you cry and make you immediately download her latest album 'Strange Trip Ahead'
📍Montreal St. Stage by The Caesar Company - 177 Princess St.
3 PM: Brock St. Drag Show
Drag is coming to the Scenic Route!
Gather round for an unforgettable drag show featuring some of Kingston’s most fabulous drag artists! Expect queens, kings and clowns celebrating the diversity, creativity and artistry of Kingston’s drag scene.
👑 Hosted by BeeWitched, featuring StreetMeat, Blowpony, Tyffanie Morgan and Sundae Mourning L.L.C!
📍Brock St. by Martello on Brock - 66 Brock St
Don't forget to eat!
At a festival like this, it's easy to get caught up in the fun and forget the basics like food. But we're in downtown Kingston, and we have the very best food spots in the city at our fingertips!
🍜 Local Restaurants | No matter what you're craving, you'll find something delicious! Check out:
🥂 Patio Season| Patios are gonna be bustling, and I'll be looking for one with a view of the stages like:
- The Grizzly Grill
- Tommy's
- The Keg
- Jack Astor's
- Olivea
- The Caesar Company
- Casa Domenico
- Union Kitchen + Cocktails
- Bobbi Pecorino's Italian Wine Bar
🌊 Waterfront Dining | Another benefit of dining downtown is the waterfront. If you want that gorgeous view, check out:
- Wharf and Feather
- AquaTerra
- The Helm Dockside Patio
- Grab some delicious takeout for a picnic in Confederation Park
There will also be plenty of unique food vendors lining Princess St. for you to discover, and licensed areas at the King St. Stage and Mainstage Concert.
2 PM - 6 PM: Party on King St. with Tiny Horse and Absolute Treat
If you're looking for party vibes and dance-all-night bops, then the King St. Stage is the spot!
🎧 DJ Graham Walsh | 2 PM - DJ Graham is gonna get the party started and keep the vibes going until Tiny Horse takes the stage.
🍻 Licensed Area | Open 2 PM | Last Call 5 PM - When you're craving a refreshing brew or canned cocktail, head over to the licensed area for some of Collective Arts' tastiest drinks. A valid 19+ photo ID is required to purchase alcohol.
🎶 Tiny Horse | 4 PM - Canada's giddy-up indie pop darlings are running wild on the King St. Stage. These Kingston legends are known for their signature dance-and-cry style, so get ready for singing, dancing and all the feels.
🎶 Absolute Treat | 5 PM - Disco, rock and R&B come together in Absolute Treat's shimmering, groove-heavy tunes, inspired by the best of '70s and '80s pop. Get ready for an absolute blast as they close out the Scenic Route.
📍King St. Stage by Peter's Place - 34 Princess St.
5:30 PM - 11 PM: Go All Out at the Mainstage Concert
The Scenic Route is wrapping up, but RoadTrip is cranking the volume to high. It's time for the main event: an all-out, full-throttle mainstage concert!
Grab your tickets and head to Springer Market Square for the ultimate last blast of summer featuring:
🎶 Katie Tupper | 6:30 PM - Polaris Music Prize-nominated singer Katie Tupper's deep, soulful vocals and effortless blend of R&B, pop, and indie vibes make for a performance that's as electric as it is captivating. Sing along and try not to get hypnotized.
🎶 Kasador | 7:15 PM - These local Kingston legends have built their name on explosive live shows, massive riffs, and no-nonsense rockstar energy. This is loud, full-throttle, hands-in-the-air music you have to hear.
🎶 Gabriel Jacoby | 8:15 PM - R&B's most exciting rising star, Gabriel Jacoby, is bringing the groove and the funk to the RoadTrip mainstage. His out-of-this-world falsetto, one-of-a-kind rasp and ear-worm beats will keep you dancing all night.
🎶 Peach Pit | 9:15 PM - I've been waiting all day for this one: headliner Peach Pit finally takes the stage! Their dreamy, laid-back indie rock tunes, catchy grooves and sun-soaked melodies are going to be the perfect way to end the night. And honestly, they just seem like cool guys. If friendship had a sound, it would be Peach Pit.
Gates open at 5:30 PM. I'll be getting there right on time so I can snag a drink and a spot as close to the stage as possible.
🍻 Licensed Area | Open 5:30 PM | Last Call 10:15 PM - Need a little refreshment? The licensed area has you covered with Collective Arts' brews and canned cocktails. Valid 19+ photo ID required for alcohol purchases.
📍Mainstage in Springer Market Square - 1 Market St.
Just a few more tips for the road:
- Take lots of pictures and tag us @roadtripkingston and @downtownkingston
- Make sure to shop local and support the 700+ downtown businesses that made this festival possible.
- Stay hydrated, wear comfy shoes, bring your besties and have fun!
And that's a wrap on the very first RoadTrip Music Festival! Already can't wait for RoadTrip 2027!
Join the ride on September 12th, 2026.
It's the first year of an all-new festival: you'll want to say you were there!
RoadTrip is proudly sponsored by TD, Rogers Sports & Media, K-Rock 105.7, Country 93.5, Kingston Marriott, Queen's AMS, OCAF, Kingston Accommodations Partners, Collective Arts, Farm Boy, and Kingston Live!
Sierra Saikaley
Marketing and Communications Producer at Downtown Kingston










