Caleb Rosson
Overview
Solo acoustic guitarist and singer in St. Louis — weddings, corporate events, private parties, wineries, and restaurants. Also travels to Kansas City and Louisville.
300+ songs: country, 2000s pop, classic rock, and alternative. I can stay conversation-friendly during dinner or push it forward and get people dancing — your call.
Fully self-contained with my own professional PA. No sound tech to hire; I just need an outlet. I arrive early, dress for the event, and keep the volume where you want it.
Recorded at Harbor Studios, opened for Julia Cole at Old Rock House. Happy to learn a special song for a first dance or anniversary — just send it over.
Reviews
2 reviews
Cori D.
August 27, 2026Excellent
Caleb is so very talented! Hired him for the morning of a golf outing and everyone loved him. He is great at what he does and is a great communicator leading up to the event as well. Definitely recommend!
Hired as: Singing Guitarist
Sarah M.
August 5, 2024One of the best local musicians
Caleb played at our event and was phenomenal. Not only does he have a great voice, but his songwriting is some of the best I’ve ever heard. He had us in tears at times and dancing other times! We’ve hired him for multiple events now and never disappoints. His sound system was great for our 100+ person event. Be sure to ask about originals! Majority of his music is the country genre, but he plays some pop songs along with alternative and other hits.
Hired as: Singer/Songwriter
Booking information
Price range: $300-$900
Languages: English
Gig length: 30 - 300 minutes
Insurance: $1,000,000 - $1,000,000 per occurrence / $2,000,000 aggregate.
What to expect
I respond to every request within a few hours, usually faster.
Once we’re booked, we’ll do a 20–30 minute call to talk through your event — timeline, guest count, vibe, and any must-play or do-not-play songs. If there’s a specific song that matters for a first dance, an anniversary, or a guest of honor, send it my way and I’ll have it ready.
Day of, I arrive at least 45 minutes early to set up and sound check before guests arrive. I dress for your event and check in with you before I start so the volume is right where you want it. Setup and teardown are on me and take about 20 minutes each.
About
Here’s what booking me actually looks like. We’ll talk for 20–30 minutes beforehand about your event, your guests, and any songs that matter to you. If you want something specific for a first dance, an anniversary, or a guest of honor, send it over and I’ll learn it. I show up early, dress for the occasion, and bring my own professional PA — no sound tech to hire, nothing for you to coordinate. All I need is an outlet.
I can stay quiet and conversation-friendly through dinner, or turn it up and get people dancing. I’ve played a two-song wedding ceremony, a four-hour cover set, and a one-hour show of all originals. Whatever the night calls for.
I also write and record. My latest single was cut at Harbor Studios in Alton, and I opened for Julia Cole at Old Rock House in St. Louis. My originals are on Spotify and Apple Music if you want to hear that side of it.
Additional booking notes
I’m fully self-contained: professional PA, mics, stands, and cables. All I need is one standard electrical outlet within about 50 feet of where I’ll set up.
My footprint is roughly 6x6 feet. For outdoor events, I just need shade or cover over the gear — direct sun and rain are the only real dealbreakers.
For sets over two hours I take a short break each hour and can play background music through the system so the room never goes silent.
Services offered
Upcoming booked events
October 2026
03
Saturday
Tullys Taproom
All-day event
Past booked events
August 2026
27
Thursday
Corporate Event
7:00am - 9:00am
•
Madison, IL
Set list
This changes for each gig / I have over 300 songs in the book. We will talk about the vibe and go from there!
Influences and inspiration
Leon Bridges, John Mayer, Zach Bryan, Tyler Childers, Travis Tritt, The Teskey Brothers, The Fray, Third Eye Blind, Fuel, 3 Doors Down, Marcus King Band, Brooks & Dunn
Setup requirements
Electrical Outlet
Covered Area