Pittsfield Halloween Parade Returns with Hollywood Theme

PITTSFIELD, Mass.— The city's historic Halloween parade rises from the dead this year with a Hollywood theme.

On Monday, the Department of Community Development Recreation Program announced that the "Spooky Hollywood" parade will be held on Friday, Oct. 25, at 7 p.m. on Tyler Street.

Aside from the usual ghouls, goblins, and superheroes, there will be an abundance of spooky pop culture icons. Think the Sanderson Sisters from "Hocus Pocus," Michael Myers from the "Halloween" franchise, or even Casper the Friendly Ghost.

"Participants are encouraged to base their float designs, decorations, and/or costumes around their favorite Halloween movie," the department wrote. "Every school and community/civic group is encouraged to participate in this great Pittsfield tradition."

This will be the 78th Halloween parade in the city. It was originally held on North Street and was moved to Tyler Street in 2011.  

Trick-or-treat is scheduled for Thursday, Oct. 31, from 5:30 to 7 p.m. rain or shine. Participants are asked to leave their porch or exterior light on.

Every parade unit needs to review the application packet posted on the city website and a representative from interested parties must attend a float seminar on Thursday, Sept. 26, at 6 p.m. in Room 203 at City Hall.

Striking Out Cancer in Berkshires Holds Sunday Party Before June 27 Games

By Stephen DravisiBerkshires.com Sports
10:53AM / Monday, June 15, 2026

PITTSFIELD, Mass. – Striking out Cancer in the Berkshires has been bringing smiles for half a decade.

 

This year, it also is bringing Smiley.

 

A day of community baseball and softball games that act as a fund-raiser for the Jimmy Fund is the brainchild of Joe DiCicco, who has expanded the event’s footprint over the years and seen a steady growth in money raised as a result.

 

This year’s games are scheduled for 9:30 a.m. on June 27 on Buddy Pellerin Field at Clapp Park.

 

But the festivities begin this Sunday from 2 to 4 p.m. at the Sideline Saloon on Fenn Street, where DiCicco invites families to come down, free of charge, to take photos with a Boston Red Sox World Series Trophy and meet Boston mascot Wally the Green Monster and Smiley, the mascot of the Triple-A Worcester Red Sox.

 

“It’s just a little way to give back to the community to start the week,” DiCicco said. “Last year, we had the trophy for the first time, and they want to bring it back, so that’s a good thing. Wally is different, and so is Smiley.”

 

What has not changed is DiCicco’s dedication to the Dana-Farber Cancer Institute’s Jimmy Fund, inspired by Einar Gustafson, a child who beat cancer with the help of Dr. Sidney Farber in 1948 and shared his story with the world under the name Jimmy to protect his anonymity.