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Chad Perrone w/ Cahill
City Winery LLC
Chad Perrone w/ Cahill

Chad Perrone w/ Cahill

12/05/2026
Sat 7:30 PM
Haymarket Lounge at City Winery Boston
80 Beverly Street
Boston, MA 02114
United States
from $24.00
Sale starts soon

City Winery Boston Presents Chad Perrone w/ Cahill Live on Saturday, December 5th at 7:30pm

Chad Perrone played his first show as a singer-songwriter in March 1998 at the Sad Cafe in Plaistow, New Hampshire, in front of about seventy-five friends, family, and classmates. That same year he founded the band Averi at Suffolk University in Boston. Over the next several years Averi became a fixture of the Boston scene. The band headlined the Paradise and the Avalon, shared bills with Matchbox Twenty, the Goo Goo Dolls, Guster, and Barenaked Ladies, and earned several Boston Music Award nominations along the way.

In 2006 Chad went solo, partly to give the songs more room. His debut, Used to Dream, led to more BMA nominations, including Outstanding Male Singer/Songwriter. It was followed by Wake, Kaleidoscope, Release, the Even EP, and, most recently, What Would I Leave You With (2024). Kaleidoscope was funded by fans through a PledgeMusic campaign that passed its goal. It’s a small detail, but it says a lot about the loyal audience he has built. The Boston Phoenix praised his “love stories with deep hooks” and “graceful melodies in a pleasing, high voice,” and online critics have called him one of independent music’s best-kept secrets.

His newer songs are quieter and more reflective, and they’re written from the far side of some hard years. Today Chad plays a handful of select shows each year, mostly intimate rooms where the songs have space to breathe.

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Twenty-five years ago Robert Antonelli and Scott O’Brien were dancing on their parents’ patios, lip-syncing to Michael Jackson, dreaming of performing. These days their dreams are similar but the music is their own. Cahill began performing on the streets of Harvard Square, slowly building their repertoire in front of a constantly changing landscape of passing pedestrians. They graduated to touring the college circuit in 2007 after the release of their sophomore album “At The Seams.”

Six years and over 200 colleges later, the acoustic duo is continuing their musical growth with the release of their fourth studio album, “The Way It Should Be.” This self-produced, recorded, and engineered project is a true testament to the deep history these two musicians share. Their fan base reaches all across the country thanks to their permanent residency in the world famous Faneuil Hall Street Performers Program in Boston.

Their songs have been featured on MTV, E!, NBC, and they debuted at #51 on the iTunes Singer/Songwriter chart during this latest release. In the age of downloading, the band has also found success with two viral hits on Pandora.

GA Advanced - $20 / Day of Show - $25

SP Advanced - $25 / Day of Show - $30


Dine At Your Show(opens in a new tab)

(opens in a new tab)🍽️ We provide food and beverage service directly to your table in the venue. Or, for an expanded menu and more relaxed experience, arrive early and enjoy a meal in our restaurant before the show. When dining in the restaurant, reservations are encouraged and can be made via Resy starting one month before the show. View Our Concert Dining Menu.(opens in a new tab)


2 Item Per Person Encouraged

🎶 While we do not require a two-item food or beverage minimum, we strongly encourage it. Most ticket revenue goes directly to the artist and production costs, so food and drink purchases help support the staff, service, and atmosphere that make these intimate shows possible.

The good news: we think you’ll love the food and wine just as much as the show.


Become a Vinofile Member(opens in a new tab)

🍷 Members get 48 hour early access to new shows, pay no ticket fees, and earn points to exchange for complimentary tickets. Vinofile VIP+ members also receive many wine benefits. Add a membership to your cart during checkout to start saving now. Already a member? Make sure you are signed in to access your benefits. Become a Vinofile Member and enjoy the benefits today.(opens in a new tab)

Tickets start at
$24.00
Chad Perrone w/ Cahill
Haymarket Lounge at City Winery Boston
Sale starts soon

12/05/2026
Sat 7:30 PM
Haymarket Lounge at City Winery Boston
80 Beverly Street
Boston, MA 02114
United States
from $24.00