RoadTrip Music Festival 2026: Downtown Kingston’s Musical Journey
A full day of free street festival music, followed by an electrifying evening concert
Date
Sep 12
Cost
FREE+Tickets
Where
Kingston, ON
Headliner
Peach Pit
Downtown Kingston comes alive with indie-pop, alt-rock, soul-pop, and more across four stages. Free music and community vibes all day along Princess Street, then catch the evening main stage event at Springer Market Square as RoadTrip reaches its electrifying finale.
🎸 4 stages of music
🛍 Local vendors & artisans
🍽 Restaurants & patios
👥 9-artist lineup
💡 RoadTrip is as much about the journey as the destination. Wander freely along Princess Street from 10 AM, explore local shops and eateries, then settle into Springer Market Square as the sun sets for an unforgettable main stage experience.
About RoadTrip
RoadTrip Music Festival is Kingston’s newest cultural anchor—a full day and evening celebration of community, connection, and musical discovery. It’s a festival built on the idea that the best journeys are the ones where you discover something new at every stop. Just as a great road trip blends anticipation, adventure, and memorable stops along the way, RoadTrip promises a seamless journey from daytime street celebration to an electrifying evening concert.
The inaugural 2026 festival brings together an exciting mix of emerging Canadian and local talent alongside internationally recognized artists, with local retailers, artisans, restaurants, and patios creating an irresistible downtown experience from start to finish.
🎵 The 2026 Lineup
Saturday, September 12 | Multiple Stages
Headliner
Peach Pit – Vancouver indie-pop favourites headlining the main stage evening performance. Known for catchy melodies and engaging live shows.
Featured Artists
Kasador
Kingston alt-rockers bringing local energy to the stage.
Katie Tupper
Soul-pop artist with powerful, engaging vocals.
Mariel Buckley
Alt-country songwriter with storytelling charm.
Gabriel Jacoby
Singer-songwriter bringing intimate performances.
Absolute Treat
Toronto dream-pop outfit delivering atmospheric sounds.
Princess Street Performances
Tiny Horse
Kingston local talent
Piner
Tyendinaga-based artist
O Green
Kingston and Tyendinaga artist
🌞 Daytime Festival: Princess Street Journey
10:00 AM – 5:50 PM | Free Admission
The Scenic Route Experience
Over a kilometer of downtown Kingston transforms into your personal scenic route through the heart of the city. Three stages along Princess Street fill the day with performances from noon to 5:00 PM. Wander freely with no GPS needed—explore local shops, eateries, artisans, and community groups ready to treat you to a full day of fun and discovery.
🎤 3 Stages
Multiple venues along Princess Street hosting continuous performances.
🛍 Local Vendors
Retailers and artisans throughout the street festival.
🍽 Food & Patios
Restaurants and outdoor seating throughout downtown.
👥 Family-Friendly
All-ages experience with free street festival atmosphere.
Daytime Tips
The daytime festival is completely free and best enjoyed by strolling at your own pace. Arrive early to catch performances from the beginning, or drop in anytime during the 10 AM opening. Bring comfortable walking shoes—you’ll be exploring the beautiful downtown core.
🎸 Evening Main Stage: The Finale
6:30 PM – Late | Springer Market Square (Ticketed)
When the Sun Sets
As the sun goes down, RoadTrip turns up the volume. Springer Market Square transforms into the epicenter of the festival, hosting the main stage concert featuring the headline acts. Expect high energy, a high-caliber lineup, and the ultimate end-of-summer concert experience as the festival reaches its electrifying finale.
🎟 Ticketed Event
Main stage concert requires admission ticket via Showpass.
⭐ Featured Lineup
Peach Pit headlining with featured artists throughout the evening.
🎓 Student Discount
Exclusive student pricing available with valid ID.
🏨 Hotel Packages
Bundle tickets with Kingston Marriott accommodations.
Essentials
Organizers
Downtown Kingston BIA (700+ business & property owners), Flying V Productions, Steve Jordan (Polaris Music Prize Founder), Virginia Clark (Wolfe Island Music Festival)
What to Bring
Comfortable walking shoes, sunscreen, water bottle, light jacket for evening (September weather).
Get Tickets
Daytime free. Evening concert tickets via Showpass.
Website
🎯 First-Ever Festival
RoadTrip Music Festival launches in 2026 as Kingston’s newest cultural anchor, designed to surprise, grow, and inspire year after year. The Downtown Kingston BIA hopes to expand this into a multi-day event in the future.
🚗 Getting There & Parking
Location
Daytime: Princess Street, Downtown Kingston
Evening: Springer Market Square (King Street & Brock Street)
Kingston, ON K7L 2Z3
Evening: Springer Market Square (King Street & Brock Street)
Kingston, ON K7L 2Z3
By Car
From Toronto: Take the Gardiner Expressway / QEW east toward Niagara, then follow signs toward Highway 401 east toward Kingston. The drive is approximately 2.5–3 hours to downtown Kingston.
From Ottawa: Take Highway 7 east toward Kingston (approximately 2 hours). The drive is scenic as you approach Kingston from the north.
From Ottawa: Take Highway 7 east toward Kingston (approximately 2 hours). The drive is scenic as you approach Kingston from the north.
Parking Info
Downtown Kingston has numerous parking lots and street parking available. The Springer Market Square area is accessible via Brock Street with nearby lot parking. Arrive early if driving, as on-site parking may fill during peak hours.
Public Transit
Kingston Transit serves the downtown area. The transit transfer point is conveniently located near Springer Market Square on Brock Street. For real-time schedules and routes, visit Kingston Transit.
💡 Tips for the Best Experience
Plan Your Day
The daytime festival is free and self-guided. Decide which Princess Street performances to catch, or drift between all three stages to maximize variety.
Book Evening Tickets in Advance
The main stage concert is ticketed and likely to sell out. Secure your tickets early via Showpass to guarantee entry.
Explore Downtown
RoadTrip celebrates the journey as much as the destination. Use the daytime festival to browse local shops, visit artisans, and grab lunch from downtown eateries.
Sunset Timing
The festival transitions to Springer Market Square as the sun sets around 6:30 PM. This is your cue to head to the evening venue for the main stage concert.
September Weather Prep
Late summer in Kingston can be warm during the day but cool in the evening. Bring layers, sunscreen, and a water bottle for daytime exploration.
Follow for Updates
Sign up for the RoadTrip newsletter at roadtripkingston.ca for lineup updates, ticket info, and last-minute details before the festival.
❓ Common Questions
Details may change—always confirm on the official RoadTrip Music Festival website before heading out.
Location
Get Directions1 Market St, Kingston, ON K7L 1W8
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