First Annual Transformer Comedy Fest Comes to Pittsfield

PITTSFIELD, Mass. — The Transformer Comedy Fest will feature three days of comedians from across the nation at Flat Burger Society and Dottie's Coffee Lounge.

The event runs from Thursday to Saturday at 8 p.m. with headliners Caitlin Cook, Anthony DeVito, and Josh Gondelman.

The festival is independent and homegrown festival with local and regional comics in supporting roles at each show. It is being produced by the Comedy Grotto at Flat Burger Society, a monthly professional comedy production, in cooperation with Dottie's.

Flat Burger Society is located on McKay Street and Dottie's is located at the corner of North Street and Maplewood Avenue.

Thursday, Oct. 13

Caitlin Cook kicks off the festival at the Comedy Grotto. She uses irreverent musical comedy and projected visuals and has taken the stage at top-tier comedy clubs and theaters and has released two musical comedy albums both of which are regularly featured on Sirius XM and other streaming platforms. She is currently touring "The Writing On The Stall," a one-woman bathroom stall graffiti musical that made its official debut at the Edinburgh Festival Fringe in Scotland in August.

Friday, Oct. 14

Writer and comedian Anthony DeVito takes the stage of Dottie's Coffee Lounge. He's appeared on CBS' "The Late Show with Stephen Colbert," "Comedy Central Stand Up Presents: Anthony DeVito," Comedy Central's "Adam Devine's House Party," NPR's "This American Life," TV Land's "The Jim Gaffigan Show," and AXS TV's "Gotham Comedy Live." His debut album "Dream Occupation" is available from Comedy Central Records. DeVito has created a one-person show about finding out a family secret titled "My Dad Isn't Danny DeVito" that also made its debut at the Edinburgh Festival Fringe.

Saturday, Oct. 15

On the final night, author, producer, and comedian Josh Gondelman will headline Flat Burger Society's Comedy Grotto. Gondelman is a writer and comedian who incubated in Boston before moving to New York City, where he currently lives, and most recently worked as the head writer and an executive producer for "Desus & Mero" on Showtime. Previously, he spent five years at "Last Week Tonight with John Oliver," where he earned four Emmy Awards, two Peabody Awards, and three WGA Awards. His debut standup special "People Pleaser" is available to stream now. In 2016, Josh made his late-night standup debut on "Conan" (TBS), and he has also performed on "Late Night With Seth Meyers" (NBC) and "The Late Late Show with James Corden" (CBS).

Gondelman is also the author of the essay collection "Nice Try: Stories of Best Intentions and Mixed Results" published in September 2019 by Harper Perennial. As of 2019, he has become a regular panelist on NPR mainstay "Wait Wait Don't Tell Me."

Additionally, on Tuesday, Nov. 15, comedian Eddie Pepitone, subject of the documentary "The Bitter Buddha" and creator of comedy specials for Comedy Central, HBO, and Netflix, with hundreds of entries on his IMDB page, will headline the Comedy Grotto at Flat Burger Society.

Tickets for individual shows are available in advance via www.transformerfest.com.

Nonprofit Center of the Berkshires Honors Leaders, Volunteers

By Breanna SteeleiBerkshires Staff
09:07AM / Sunday, May 24, 2026

Liana Toscanini presented the Founder's Choice Award to Smitty Pignatelli for his years of support as state representative. 

PITTSFIELD, Mass. — The Nonprofit Center of the Berkshires held its ninth annual nonprofit awards last week honoring the contributions of those who have helped the community in their own way.

 

The gathering at the Country Club in Pittsfield on Tuesday included the introduction of new nonprofit Executive Director Samantha Anderson, who steps in for retiring founder and director Liana Toscanini. State Reps. Tricia Farley-Bouvier, John Barrett III and Leigh Davis attended the event.

 

Toscanini, who created NPC in 2016, was honored at the conclusion of the evening to mark her decade leading the organization. 

 

"Founders don't just lead organizations, they are the organization in the deepest sense," said NPC Board President Emily Schiavoni. "Their relationships, their instincts, their fingerprints are on everything, and when someone has poured a decade of herself into building something from the ground up, the act of stepping back is not a simple handoff, it's an act of extraordinary trust and courage that brings me to what Leanna actually built." 

 

NPC became something of a chamber of commerce for nonprofits under Toscanini's guidance, creating a hub of support for leadership and networking for the small and large nonprofits that fuel much of the activity within the Berkshires. 

 

She developed more than two dozen programs, including Get on Board, which helps connect community members with nonprofit boards, and a giving-back guide, volunteer fairs, and a resource directory.

 

Schiavoni described Toscanini as a great mentor who has had a big impact in strengthening local nonprofits.