Although we had planned for the Local Love Arts Festival to be rain or shine, we did not anticipate a Nor’easter with temperatures in the mid-50’s, copious amounts of rain, and high wind warnings. Therefore, we are canceling the event on Sunday. Our plan will be to host something during the holiday season as part of our Festive Frolic events.
Downtown Pittsfield, Inc. hosts Local Love Arts Festival on Sunday, September 27
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.
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.
Vendors:
Auntie Kat’s Handmade Gift Shoppe
Bake My Day
Baked! Pastries & More
Birds Eye Woodcraft
Calcite & Comfrey
Chela & Co. Charcuterie
Courtney’s Creations
Dragonfly Dreams
Filament and Ink Studio
Glimmerhold Artistry
MaMa Luchi’s All Natural Handmade Products
Penny Arcade Press
Ray of Bray Laser Designs
Solarium (Anastasia Drayton)
Sure Thing Stained Glass
TRoLL Art
Truffles by Tarah LLC
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.
Downtown Pittsfield, Inc. is still accepting applications for Berkshire County based artisanal vendors to showcase their wares at the Local Love Arts Festival on Sunday, September 27, 2026, 10 am to 3 pm, at The Common on First Street.
Only those who make their own handmade products will be accepted. DPI is looking for visual artists, craftspeople, textile artists, jewelry makers, and those who make quality packaged foods and sweets. All vendors will go through an approval process, and the organizers of the Local Love Arts Festival reserve the right to reject any vendor who is not a fit for this market. Spaces are limited. The booth fee is $75, and vendors are responsible for their own tables, tents, and set-up. No resale products will be accepted. Link to apply to be a vendor: https://forms.gle/3c9u8oymsafznnfDA