2026:

March 7, Harrisonburg VA 6:30pm
The Golden Pony
Caleb Stine, Spectator Bird, and Heather Hannah

March 20, Bloomington, IN, 5:30pm
Happy Hour at The Orbit Room
Caleb Stine with Dakota Curtis
Orbit Room Info Here

March 26 to 29, Monkton, MD
Manor Mill: Cris Jacobs Songwriting Retreat
Join Caleb Stine with Cris Jacobs and friends for this inaugural retreat dedicated to the art of songwriting! Held at two picturesque historic locations in rural Baltimore County – Manor Mill and Oldfields School – this intensive weekend is an opportunity for both aspiring and established songwriters to build skills and gain confidence.

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 18, Monkton MD, 7:00pm
Caleb Stine: Songs and Stories at Star Bright Farm

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 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 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

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://www.fallingbranch.beer/

October 9, 10, 11, Darlington MD
Caleb returns to Ramblefest V!
https://www.ramblefestival.com/

Past Shows

January 1, Baltimore MD
8:30pm
Caleb Stine and Friends at 1919 (1919 Fleet St)
The Tradition continues! Come see the music in it’s natural environment–Baltimore’s great Honky Tonk, 1919. For years, every Thursday night in January has been warmed-up by the hot licks of Caleb and Friends at the January Residency. Every Thursday in January! Music starts at 8:30.

January 8, Baltimore MD
8:30pm
Caleb Stine and Friends at 1919 (1919 Fleet St)

January 15, Baltimore MD
8:30pm
Caleb Stine and Friends at 1919 (1919 Fleet St)

January 16, Cambridge MD
5pm-8pm
Caleb plays the Cambridge Ice & Oyster Festival
https://iceoysterfest.com/

January 18 Harrisonburg VA
3:00pm at First Presbyterian Church on Court Square in Downtown Harrisonburg
Caleb Joins the Soil and Seed Project, a cast of dozens, to bring to life The Mathew Project.

The Matthew: Gospel Collection was originally conceived of as a folk-opera: a 75-minute experience of the Gospel of Matthew that could be performed from start to finish in the space of an afternoon/evening concert. On January 18, join us as we get to take it full-circle, from concept to stage, with a full band performance featuring (almost) all of the musicians who contributed to the album recordings. The event is very family friendly. While there won’t be an intermission or stretch break, there will be coloring sheets during and snacks afterwards. And permission given freely to wiggle or walk or waltz around as needed throughout.

https://www.thesoilandtheseedproject.org/matthew

January 22, Baltimore MD
8:30pm
Caleb Stine and Friends at 1919 (1919 Fleet St)

January 23, Monkton MD
7:00pm – 9:00pm
Letitia VanSant and Caleb Stine at Manor Mill!
https://calendar.manor-mill.com/events/letitia-van-sant/

January 25, Columbia MD
Caleb opens for Charm City Junction at The Encore in Columbia MD!
The Collective – Encore
10221 Wincopin Circle
Columbia, MD 21044
Tickets Here

January 29, Baltimore MD
8:30pm
Caleb Stine and Friends at 1919 (1919 Fleet St)

January 31, Roanoke VA
Caleb joins a stellar cast for WNRN’s Dead Air 5!
Dead Air returns with Dead Air V: Dark Star City on January 31, 2026 at the Jefferson Center in Roanoke! Join WNRN and more than 20 bands jamming more than 20 Grateful Dead tunes into one great night.
https://wnrn.org/deadair/

February 6, Easton MD
7pn
Across The Harbor returns to The Avalon Theater!
Get your tickets here:
https://www.avalonfoundation.org/event/across-harbor-1