2026:

Friday, October 30th, Chestertown, MD
Caleb Stine is joined by his new bluegrass project, the Acoustic Sunshine, to play Sultana Downrigging Music Festival.
Tickets on sale here: Downrigging ’26 Tickets

Saturday, November 7th, 2:30 – 4 pm, Baltimore, MD
Caleb and his band play BrewFest at Patterson Park!
40+ local beers, food trucks and restaurants and great live music, all to benefit “Baltimore’s Best Backyard”, Patterson Park! This event is rain or shine. Kids 16 and under are FREE! This event is a fundraiser to benefit the Friends of Patterson Park. Get your tickets here: Brewfest Tickets

Wednesday, November 11th, Cleveland, OH
Kitchen Table Songs
Music and Interview with Ed Sotelo

Saturday, November 14th, Bel Air, MD
Caleb plays Pairings Bistro

Friday, November 20th, Harrisonburg, VA, 7 -10 pm
Caleb joins eight other acts for a “Rainbow Cover Show,” organized by the colorful Chris Howdyshell at Harrisonburg’s newest venue, Wizard Mode. Donations go towards Rocktown House of Music.

Saturday, November 28th, Harrisonburg, VA
Round the Mountain returns! Join us at the Church of Incarnation for an evening of live music by Caleb, Spectator Bird and friends and masterful crankies performed by Katharine Fahey and Dan Van Allen. Kids 12 and under are free.

Sunday, December 13th, Lewes, DE, 7:00 pm
Caleb plays an intimate, solo show at The Listening Booth in Lewes, DE
Tickets on sale here: Listening Booth, 12/13

2027:

Saturday, January 2nd, Monkton, MD, 7 pm
Caleb Stine and Anthony Frijia play Manor Mill. Join these two songwriters and friends for an inspiring night of song.
Tickets on sale here: Manor Mill, 1/2

Saturday, January 9th and Sunday, January, 10th, Thomas, WV
Caleb plays the Purple Fiddle, 12 – 3 pm
More info here: Purple Fiddle, 1/9 and 1/10

Past Shows:

Wednesday, July 15th, Richmond, VA
AnyFolk Showcase at Vasen Brewing Company in Forest Hill
6 pm Social Hour, 7 pm Music, FREE
5047 Forest Hill Ave Ste A, Richmond, VA 23225

Saturday, July 26th, Street MD, 1-5pm
Caleb plays at Falling Branch Brewing
825 Highland Rd, Street, MD
https://www.fallingbranch.beer/

Thursday, July 30th, Damascus, VA
Caleb Stine plays with Spectator Bird at Cardinal Music Hall
Doors at 7, Music at 7:30, Tickets: $20
124 West Laurel Avenue Damascus, VA, 24236
https://www.cardinalmusichall.com/shows/spectator-bird/

Wednesday, August 5th and Thursday, August 6th, Cape May NJ, 6pm
First Wednesday and Thursday of the month from June – Sept
Caleb returns to the Historic Chalfonte Hotel!
https://www.chalfonte.com

Saturday, August 8th, Monkton, MD 3pm – 8pm
Caleb Stine Band plays 2 sets at the glorious Star Bright Farm
4pm Acoustic Set 6pm Electric Sunset Set

Sunday, August 16th, Buena Vista, CO, 4pm
Caleb plays the Hideout in beautiful Buena Vista, Colorado

Saturday, August 22nd – Roanoke, VA
Dead Air V! Come join us at The Jefferson Center as more than 20 of those bands perform their interpretation of more than 20 different Grateful Dead tunes on the same stage in one musical night, one after the other! Can we pull off this feat? Come dance, sing along, and see for yourself – all proceeds go to support WNRN and several community non-profits that make our area the special place that it is.
Get your tickets here: www.jeffcenter.org/events/dead-air-v

Wednesday, Sept 2nd and Thursday, September 3rd, Cape May NJ, 6pm
First Wednesday and Thursday of the month from June – Sept
Caleb returns to the Historic Chalfonte Hotel!
https://www.chalfonte.com

Sunday, September 13th, Fort Worth, TX, 6:00 pm
Caleb Stine and Thurman Love play The Post. Tickets: $10

Tuesday, September 15th, San Antonio, TX, 8:30 pm
Intimate song swap with Thurman Love and Caleb Stine at The Lonesome Rose. Tickets: $10

Wednesday, September 16th, Corpus Christi, TX, 7:00 pm
Caleb Stine and Thurman Love play The House of Rock.

Thursday, September 17th, Buda, TX, 7:00 pm
Caleb Stine and Thurman Love play the Meridian in Zoi Market. Tickets: $10 advance

Friday, September 18th, Austin, TX, 8:00 pm
Caleb Stine and Thurman Love play Sessions on Mary
Sessions on Mary, 604 W Mary St, Austin Texas

Friday, September 25th, Cockeysville, MD, 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/

Thursday, October 15th, Baltimore, MD, 8 pm
Caleb plays the 8 x 10, opening for Rhett Miller (of the Old 97s)
Tickets available here:
8×10 with Rhett Miller

Friday, October 23rd, Cockeysville, MD, 6pm
Caleb Stine plays Andy Nelson’s BBQ. BYO chair and beverage!

Saturday, October 24th, Baltimore, MD
Private Event