Singer-Songwriter Events in Boston

Shayfer James, Katacombs

Sun, 17 May 2026 at 3:00 PM

Sonia (The Middle East)

Music

An all-ages indie-night at The Middle East’s Sonia with Shayfer James and Katacombs, blending moody folk and indie rock. The 7pm doors promise an intimate, live-music vibe in a storied Cambridge venue, with advance tickets from $22 and door pricing up to $29.

Lissie

Sun, 17 May 2026 at 3:30 PM

City Winery Boston — Main Stage

Music

Experience an intimate night with Lissie at City Winery Boston's Main Stage, joined by Hannah Connolly. Expect guitar-driven folk-pop and soulful vocals in a warm, upscale venue renowned for live music.

Dan Rodriguez

Sun, 17 May 2026 at 3:30 PM

Haymarket Lounge at City Winery Boston

Music

Dan Rodriguez headlines Haymarket Lounge at City Winery Boston for an intimate singer-songwriter evening. Expect melodic storytelling and folk-inflected originals delivered with warm acoustic guitar in a cozy, wine-bar atmosphere, perfect for fans of heartfelt live music.

An Evening With Lucinda Williams and Her Band

Fri, 22 May 2026 at 4:00 PM

The Chevalier Theatre

Music

An evening of Americana and singer-songwriter classics as Lucinda Williams and her band headline the Chevalier Theatre. Expect a career-spanning set, intimate guitar work, and a warm, attentive audience in Medford.

EDWIN HONORET

Thu, 28 May 2026 at 4:00 PM

The Rockwell

Music

Edwin Honoret headlines The Rockwell for an intimate evening of melodic songs and storytelling. Presented by Get To The Gig, this live show spotlights a rising singer-songwriter in a warm, club-like LA venue known for close-up performances and eclectic crowds.

Ben Folds

Wed, 3 Jun 2026 at 3:30 PM

Symphony Hall

Music

Ben Folds performs piano-driven pop-rock at Symphony Hall in Boston on June 3, 2026 at 7:30 PM. Expect witty storytelling, soaring piano lines, and crowd-pleasing melodies in an intimate concert-hall setting.

Stephen Lynch: The Me Tour

Wed, 3 Jun 2026 at 3:30 PM

City Winery Boston — Main Stage

Music

Stephen Lynch brings The Me Tour to City Winery Boston for a night of guitar-driven stand-up songs and witty storytelling. Expect witty, self-deprecating humor wrapped in catchy melodies, with Lynch performing his signature comedic songs. A high-energy, intimate concert blending music and comedy in a wine-bar atmosphere.

Andy Hull

Fri, 5 Jun 2026 at 3:30 PM

City Winery Boston — Main Stage

Music

Andy Hull performs at City Winery Boston on the Main Stage, presenting intimate, guitar-driven songs from his Brother Bird project. An indie-leaning night of thoughtful storytelling in a refined winery setting. Expect warm acoustics, careful arrangements, and a focused listening vibe.

Alejandro Aranda

Mon, 8 Jun 2026 at 3:30 PM

City Winery Boston — Main Stage

Music

Alejandro Aranda delivers a genre-fluid set blending folk, pop, and experimental rock at City Winery Boston's Main Stage. Known for intricate fingerstyle guitar and haunting harmonies, his immersive performance promises evolving textures and intimate, wine-friendly vibes in a refined venue.

Perry Maysun: A Very Pathetic Tour

Sun, 14 Jun 2026 at 3:30 PM

City Winery Boston — Main Stage

Music

Perry Maysun brings his witty, heartfelt performance to City Winery Boston's Main Stage for 'A Very Pathetic Tour.' Expect intimate storytelling, melodic indie-pop textures, and a warm, wine-bar atmosphere that makes this a playful, all-around evening.

Kiefer Sutherland: Love Will Bring You Home Tour

Sun, 14 Jun 2026 at 4:00 PM

The Wilbur Theatre

Music

An intimate, storytelling-filled live concert as Kiefer Sutherland brings his Love Will Bring You Home tour to The Wilbur Theatre in Boston. Expect country-tinged folk songs, cinematic banter, and a warm, theater-friendly atmosphere in a classic venue.

Joshua Slone

Mon, 15 Jun 2026 at 2:30 PM

Royale Nightclub Boston, MA

Music

Joshua Slone headlines a live show at Royale Nightclub in Boston. Doors open at 6:30 pm, show starts at 7:30 pm with opening acts in a buzzing club setting. A contemporary indie-pop night with strong vocals and a lively, intimate atmosphere in a classic Boston venue.

In Through The Locked Door

Wed, 24 Jun 2026 at 3:00 PM

Middle East - Corner/Bakery

Music

An intimate evening of pop and singer-songwriter storytelling at the Middle East’s Corner/Bakery in Boston. Expect melodic hooks, candid lyrics, and an up-close performance in a beloved venue known for its warm, club-style atmosphere.

Jesca Hoop

Sat, 27 Jun 2026 at 3:30 PM

City Winery Boston — Main Stage

Music

Jesca Hoop headlines the Main Stage at City Winery Boston, delivering intimate singer-songwriter songs rooted in indie folk and cinematic pop. A refined evening of intricate melodies, storytelling, and magnetic live merit in a warm wine-bar venue.

Elijah Scott

Fri, 3 Jul 2026 at 3:30 PM

Haymarket Lounge at City Winery Boston

Music

Elijah Scott headlines a night at the Haymarket Lounge inside City Winery Boston, delivering country-Americana storytelling with a modern, soulful edge. Expect intimate performances of tracks like Cigarettes and Turnin Into Something, blending small-town roots with urban rhythm in a lively, singer-songwriter setting.

Sarah McLachlan - Better Broken Tour

Fri, 10 Jul 2026 at 3:30 PM

Leader Bank Pavilion

Music

Sarah McLachlan headlines the Better Broken Tour at Boston's outdoor Leader Bank Pavilion. The show is July 10, 2026, with doors at 6:30 pm and the concert at 7:30 pm; rain or shine. All support acts subject to change. An intimate, melodic evening from a renowned singer-songwriter in an iconic venue.

Howie Day

Tue, 14 Jul 2026 at 3:30 PM

City Winery Boston — Main Stage

Music

Howie Day headlines City Winery Boston on the Main Stage with an intimate, piano-and-guitar driven set. Expect heartfelt singer-songwriter pop, soaring melodies, and Day's warm, engaging storytelling that connects with the crowd.

2026 Golf Course Concert Series: Zion Rodman

Thu, 23 Jul 2026 at 2:00 PM

William J. Devine Golf Clubhouse1 Circuit Drive, Dorchester

Music

Join Zion Rodman for an outdoor concert on the patio of the William J. Devine Golf Course in Dorchester. This free, city-hosted summer music series brings live performances to a scenic golf-course setting, perfect for a casual evening of music outdoors.

Tori Amos: In Times of Dragons Tour

Fri, 31 Jul 2026 at 3:30 PM

Leader Bank Pavilion

Music

Grammy-nominated singer-songwriter Tori Amos headlines the In Times of Dragons Tour at Leader Bank Pavilion in Boston. Expect intimate, piano-led storytelling and a dynamic live show; doors at 6:30pm with showtime at 7:30pm, rain or shine.

Noah Richardson Live in Boston

Fri, 31 Jul 2026 at 4:00 PM

Haymarket Lounge at City Winery Boston

Music

Noah Richardson brings alt singer-songwriter charisma to Haymarket Lounge at City Winery Boston. This intimate live show features catchy tracks and soulful storytelling, anchored by his rising hit Tangerine and a polished, energetic performance in a chic Boston venue.

Mat Kearney: Nothing Left to Lose Everything to Gain Tour

Fri, 21 Aug 2026 at 4:00 PM

The Chevalier Theatre

Music

Mat Kearney brings his Nothing Left to Lose Everything to Gain Tour to Chevalier Theatre in Medford. An intimate evening of melodic pop and singer-songwriter storytelling with polished piano and engaging vocals, in the historic Boston-area venue.

Ariel Posen

Wed, 26 Aug 2026 at 3:00 PM

Sonia (The Middle East)

Music

A soulful indie-inspired set by Ariel Posen at Sonia, presented by The Middle East. This all-ages show opens doors at 7 PM with tickets $25 in advance and $30 on the day of, plus a note about ID to drink. No smoking inside; options to dine and skip lines add to the night’s casual yet lively concert vibe.

Rufus Wainwright

Sun, 13 Sept 2026 at 2:00 PM

City Winery Boston — Main Stage

Music

Rufus Wainwright performs at City Winery Boston's Main Stage in an intimate, piano-driven concert. Expect lush, art-pop songs delivered in a refined wine-bar setting, offering an immersive evening of sophisticated melodies in Boston.

Paula Cole: This Fire 30th Anniversary

Fri, 18 Sept 2026 at 4:00 PM

The Wilbur Theatre

Music

Paula Cole celebrates 30 years of her breakout album This Fire with a live performance at The Wilbur Theatre in Boston. Expect an intimate, singer-songwriter set with hits from the late '90s and stories behind the songs.

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