Chad Perrone w/ Cahill
Chad Perrone and Cahill perform live at City Winery Boston’s Haymarket Lounge on December 5, 2026. Perrone’s intimate singer-songwriter set draws from a career that began in 1998, including his years fronting Boston band Averi, his solo recordings, and his latest album, *What Would I Leave You With* (2024).
The acoustic duo Cahill, Robert Antonelli and Scott O’Brien, grew from Harvard Square street performances into college-circuit touring musicians. Their four studio albums, television and streaming exposure, Faneuil Hall Street Performers Program residency, and nationwide following reflect a long-running partnership built around original music.
When: Saturday, December 5, 2026
Showtime: 7:30 PM
Doors: 6:00 PM
Venue: Haymarket Lounge at City Winery Boston
Address: 80 Beverly Street, Boston, MA 02114
Tickets: General Admission is listed at $20 in advance or $25 on the day of the show. The SP tier is listed at $25 in advance or $30 on the day of the show. The event listing also states that tickets start at $24, so final prices may vary by fees or ticket type.
Ticket link: https://tickets.citywinery.com/event/chad-perrone-w-cahill-w5mvno
Headliner: Chad Perrone
Opening act: Cahill, featuring Robert Antonelli and Scott O’Brien
Chad Perrone background: Perrone began performing as a singer-songwriter at the Sad Cafe in Plaistow, New Hampshire, in March 1998. He founded Averi at Suffolk University that same year, and the band later headlined Boston’s Paradise and Avalon and shared stages with Matchbox Twenty, the Goo Goo Dolls, Guster, and Barenaked Ladies. After going solo in 2006, Perrone released *Used to Dream*, followed by *Wake*, *Kaleidoscope*, *Release*, *the Even EP*, and *What Would I Leave You With* in 2024. His recent material is quieter and more reflective, and he now performs a limited number of shows each year, primarily in intimate venues.
Cahill background: Antonelli and O’Brien began by performing on the streets of Harvard Square before moving into college touring in 2007 after releasing *At the Seams*. After playing more than 200 colleges over six years, they continued developing their sound with *The Way It Should Be*, a self-produced, recorded, and engineered fourth album. Their music has appeared on MTV, E!, and NBC, and their latest release reached No. 51 on the iTunes Singer/Songwriter chart. They have also had two viral hits on Pandora.
Dining: Food and beverage service is available at tables during the concert. Guests may also arrive early for a meal in the restaurant, where reservations are encouraged through Resy beginning one month before the show.
Venue note: A two-item-per-person food or beverage purchase is encouraged, but the venue does not require a minimum.
Run time: Not provided.
Age policy: Not provided.
Accessibility information: Not provided.