Shows
2026:
April 9, Columbia MD, 7:30pm
Charm City Junction with Caleb Stine
At The Collective – ENCORE in Columbia MD
Tix and Info here
April 10, Baltimore, MD, 7:30pm
Music On The Square Presents: Caleb Stine and Spectator Bird
Friday, April 10
Music on the Square – 1025 S. Potomac St, Baltimore, MD
Doors 7:00pm | Show 7:30pm
$25 | Kids 12 and under free
https://www.alexlacquement.com/music-on-the-square-concert-series.html
April 12, Rockville, MD 6:00pm
Caleb Stine opens for Peter Case
Doors at 6:00pm Caleb starts at 6:30pm
HANK DIETLE’S TAVERN 11010 Rockville Pike Rockville, MD, 20852
April 18, Monkton MD, 6:00-8:00pm
Caleb Stine: Songs and Stories at Star Bright Farm
Join us for an intimate evening of Songs and Stories in the Barn
Light food/snacks/Beverages will be available. Doors open at 4:30 for Barn Market shopping
May 6, Baltimore MD, 7:00pm
Pickett Brewing
Caleb Stine, Walker Teret, and Tim Newby share songs and stories of Townes Van Zandt
More info TBA
https://pickettbrewingco.com/
May 8, Chestertown, MD, 8:00pm
The High and Wide’s return to the Garfield Stage, joining them will be singer/songwriter Caleb Stine
Garfield Center for The Arts, at the Prince Theater.
https://www.eventbrite.com/e/the-high-and-wides-with-caleb-stine-tickets-1986330493978
May 9, Monkton, MD
Monkton Music Festival Returns!
Catch the Caleb Stine Band and many more!
Join us for our annual Monkton Music Festival May 9, 2026 — a one-day celebration of live music, local flavor, and the great outdoors! Nestled in the scenic hills of Monkton, this family-friendly event features:
*Two stages of live music from 10 regional and local artists
*Artisan vendors and craft booths
*Delicious eats from local food vendors
*A beautiful rustic setting surrounded by nature
https://www.camppuhtok.com/events
May 16, Baldwin, MD 4pm-7:30pm
Hybridoma Farm
Caleb plays solo
13734 Baldwin Mill Rd., 21013
Hybridoma Farm is a working agricultural farm focused on organic blueberry production!
May 23, Harrisonburg, VA, 6pm-10pm
Honky Tonk Dance Party at Pale Fire Brewing
Come for a family friendly, community dance! Old School vibes with a live band and Western Wear encouraged. Come out and learn how to Two-Step in the welcoming environment of Pale Fire!
First Wednesday of the month from June – October
Caleb returns to the Historic Chalfonte Hotel! More info tba
https://www.chalfonte.com
June 6, Massanutten, VA, 7pm
The Caleb Stine Band plays at Massanutten Resort
June 20, noon – 9pm
Caleb Stine Band at Harmony Woods Festival
July 3, Massanutten VA
Massanutten Resort is proud to present to you Summer Jam 2026! The event will feature live music, kids’ activities, beer & wine, food trucks, plus one of the largest fireworks show in the area around 10 pm!
Mo-Grass | 8:30 – 10:00 PM
The Caleb Stine Band | 6:15 – 7:45 PM
SJ McDonald | 4:30 – 5:30 PM
https://events.humanitix.com/https-www-massresort-com-play-live-events-summer-jam?c=caleb-stine
July 26, Street MD, 1-5pm
Caleb plays at Falling Branch Brewing
https://www.fallingbranch.beer/
August 8, Monkton, MD 3pm – 8pm
Caleb Stine Band plays 2 sets at the glorious Star Bright Farm
4pm Acoustic Set 6pm Electric Sunset Set
August 16, Buena Vista, CO, 4pm
Caleb plays the Hideout
Sept 13-19
Caleb Solo in Texas
Sept 23 6pm
Caleb Stine and The Lawless at Andy Nelson’s BBQ
October 9, 10, 11, Darlington MD
Caleb returns to Ramblefest V!
https://www.ramblefestival.com/