Stage:

The Main Stage Event

Hour:

8:15pm

Gabriel Jacoby

Rising R&B artist blending funk, soul, and modern influences. Originally from South Carolina, he began making music at a young age and quickly built a passionate fan base with singles like “Forever,” “Be Careful,” and “The One.” Often compared to legends like Prince, D'Angelo, and Maxwell, Jacoby brings a fresh yet timeless sound to contemporary R&B while focusing on authenticity, connection, and uplifting his listeners.

RoadTrip on Spotify

RoadTrip on Spotify

Watch a music video

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Discover their music

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Their History

After several standout singles and his 2025 debut project

Born in Anderson, South Carolina, Gabriel Jacoby grew up in a creative household that encouraged his passion for music. He began playing piano at a young age and later expanded his skills to bass, drums, guitar, and production after his family moved to Tampa, Florida. As a teenager, he started recording music in a home studio and sharing songs on SoundCloud, quickly gaining attention with early releases like “Mr. Poet.” Over time, his sound evolved from rap into a rich blend of R&B, funk, and soul, drawing comparisons to artists like Prince, D'Angelo, and Maxwell. After several standout singles and his 2025 debut project, Jacoby continues to grow as an artist focused on authenticity, connection, and uplifting his audience.

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Where have they performed?

Supporting artist Khamar

Gabriel Jacoby has performed at various venues across the U.S. and Canada, often supporting artist Khamari. Notable stops on his 2026 tour include the 9:30 Club (Washington, DC), El Rey Theatre (Los Angeles), and Danforth Music Hall (Toronto).

What to Expect at RoadTrip?

Access to the main stage performances in Springer Market Square

You’ve arrived! Your ticket grants you access to the high-energy, high-caliber main stage concert in Springer Market Square.

What Your Ticket Includes:

Main Stage Access

RoadTrip is as much about the journey as the destination. From 10 am to 5:50 pm, over a kilometer of downtown Kingston's vibrant Princess Street transforms into your personal scenic route through the heart of the city, lined with local shops, eateries, artisans and community groups ready to treat you to a full day of fun. Wander freely with no GPS needed.

The Scenic Route Experience

A walkable journey through music and community

When the sun goes down, RoadTrip turns up the volume! The festival moves to Springer Market Square for an unforgettable night of main stage performances. Buckle up for high energy, big crowds and the ultimateend-of-summer concert.

The Destination:

Main Stage Concert - Ticketed

RoadTrip is a one-dayjourney of musical exploration. From emerging Canadian and local talent to internationally recognized artists, unique performances will unfold across multiple stages, giving you the chance to discover new favourites and leave with a playlist you can't stop listening to.

A Full Day of Music to Discover

From morning discovery to nighttime concerts

When the sun goes down, RoadTrip turns up the volume! The festival moves to Springer Market Square for an unforgettable night of main stage performances. Buckle up for high energy, big crowds and the ultimateend-of-summer concert.

The Destination:

Main Stage Concert - Ticketed

Access to the main stage performances in Springer Market Square

You’ve arrived! Your ticket grants you access to the high-energy, high-caliber main stage concert in Springer Market Square.

What Your Ticket Includes:

Main Stage Access

RoadTrip is as much about the journey as the destination. From 10 am to 5:50 pm, over a kilometer of downtown Kingston's vibrant Princess Street transforms into your personal scenic route through the heart of the city, lined with local shops, eateries, artisans and community groups ready to treat you to a full day of fun. Wander freely with no GPS needed.

The Scenic Route Experience

A walkable journey through music and community

RoadTrip is a one-dayjourney of musical exploration. From emerging Canadian and local talent to internationally recognized artists, unique performances will unfold across multiple stages, giving you the chance to discover new favourites and leave with a playlist you can't stop listening to.

A Full Day of Music to Discover

From morning discovery to nighttime concerts