Upcoming Performances

September 25, 2026 – Brent Calderwood at Havalina
Havalina / Portland, 9:00pm
50-minute set; night shared with songwriter-performer with Wendy Emerson (separate set).

November 5, 2026 – Songwriter Showcase with Brent Calderwood, Wendy Emerson, Richard Colombo, and Inge Hoogerhuis
Artichoke Community Music / Portland, 7:00pm
Four songwriters featured at special showcase event. Nashville-style round, artists will play 5 songs each with storytelling and collaboration.

Recent Performances

September 3, 2026 – The Bridge with Emerson Parker, Winsom, and Brent Calderwood
Artichoke Community Music / Portland
Featured songwriter-performer in Portland Songwriters Guild’s monthly listening-room songwriter showcase. URL: https://www.youtube.com/watch?v=mfzn91zqjUE

August 25, 2026 – SingAcoustic Open Mic cohosted by Brent Calderwood
SingAcoustic / Portland
Guest host/emcee and featured performer for SingAcoustic’s open mic event.

May 13, 2026 – Brent Calderwood at Americana Happy Hour
The Hostel Café / Portland
60-minute set, Brent Calderwood (guitar/vocals/piano) featured at the Hostel Cafe’s weekly Americana Happy Hour. Played with guest bandmates Flux (piano), Richard Colombo (guitar), and Wendy Emerson (guitar/vocals); also played piano for Wendy Emerson’s set. URL: https://everout.com/portland/events/trans-gay-queer-songwriter-showcase/e239608

February 14, 2026 – Brent Calderwood at Americana Happy Hour
The Hostel Café / Portland
60-minute set, Brent Calderwood (guitar/vocals/piano) featured at the Hostel Cafe’s weekly Americana Happy Hour. Guest bandmates Flux (piano) and Richard Colombo (guitar).

November 26, 2025 – Brent Calderwood at Artichoke’s Queer Open Mic
Artichoke Community Music / Portland
3-song set as featured guest performer at Artichoke’s monthly Queer Open Mic.

May 19, 2023 – RADFAF Arts Festival
Falcon Building / Portland
Featured performer in music showcase, part of 5-day LGBTQ+ art festival including film festival, art gallery, spoken word, music, dance, and theater. Also featured at May 18 spoken word event and volunteered my marketing and film editing services. URL: https://www.radfaf.org