The inaugural Local Love Arts Festival will take place on Sunday, September 27, 2026, from 10:00 am to 3:00 pm at The Common in Downtown Pittsfield. Local artists will take center stage — showcasing their work, connecting with new audiences, and reminding our community that some of the region’s most talented creators are right here in our own backyard.

The event will celebrate the incredible talent of Berkshire County’s artists while creating a vibrant Downtown experience filled with art, music, food, family activities, and community. Visitors will enjoy 20+ artisanal vendor booths, the Berkshires Jazz Summer Showcase, food and beverages, a children’s activity area with free face painting and balloon twisting, sidewalk chalk art with Pittsfield Parks and Rec, and interactive arts experiences throughout the day. Hot Plate Brewing Co. will host an exclusive beer and wine garden with a view of the Main Stage.

Bruce Bowey of BTC Family Entertainment will host a free, family-friendly magic show that contains some puppet routines and some ventriloquism.

Live jazz entertainment will be provided by Berkshires Jazz throughout the event. Performers include Junk, featuring Will Hudgins on vibraphone; Joe Finn with Jack Dinicola and Friends; and The Wanda Houston Band. A schedule will be posted to downtownpittsfield.com. The Berkshires Jazz Summer Showcase is sponsored by the Berkshire Eagle, Pittsfield Cultural Council, and Mill Town Foundation.

Artists Mike Carty and Diane Firtell will be painting live during the event, Berkshire Art Center will be providing an interactive art activity, and Katunemo Art & Healing will host a Faces of Pittsfield community art project.

Pittsfield Parks & Recreation will host chalk art drawing for the duration of the event. People of all ages and abilities are invited to transform the paved walking paths of The Common into a vibrant outdoor gallery using sidewalk chalk. There is no competitiveness to this activity; it’s just an opportunity to create, connect, and enjoy art in a welcoming, family-friendly atmosphere. Whether you’re a seasoned artist or simply looking to draw for fun with friends or family, everyone is invited to participate. There will be some pre-taped squares along the pavement at the front of the park which will be available on a first-come, first-served basis as well as a dedicated kids’ drawing area.

A portion of the proceeds from the festival will support Downtown Pittsfield, Inc.’s ongoing work to promote local businesses, public art, placemaking, and community events throughout Downtown Pittsfield.

The Local Love Arts Festival is sponsored by the Massachusetts Cultural Council, Mill Town Foundation, and the Feigenbaum Foundation.