Winners of the 2025 Pittsfield Photo Challenge Announced
The winner of DPI’s 2025 Photo Challenge, as determined by local judges, is Charles Flint. His photo taken from the bridge on Cloverdale Street and Route 20 in Pittsfield has won him a $100 Downtown Pittsfield Gift Card.
Bridge on Cloverdale Street and Route 20 in Pittsfield by Charles Flint
The second-place winner of DPI’s 2025 Photo Challenge, Talia Magnani, has won a $50 Downtown Pittsfield Gift Card for their photo of the sunset downtown taken from the top of their building.
Downtown Sunset by Talia Magnani
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Pittsfield Photo Challenge is accepting entries through November 7, 2025
Downtown Pittsfield, Inc. is once again holding a photo challenge to find the photo that best captures why Pittsfield is the “Heart of the Berkshires”. Entrants are encouraged to capture photos that showcase the beauty and personality of downtown Pittsfield, keeping in mind the theme “Heart of the Berkshires”. Creativity is encouraged. Please only submit images in the spirit of positivity.
The first place winner, as determined by a panel of local judges, will have their photo featured in Pittsfield’s 2026 Downtown Guide. The first place winner will win a $100 Downtown Pittsfield Gift Card. The second place winner will win a $50 Downtown Pittsfield Gift Card.
Downtown Pittsfield, Inc. will accept photo submissions through Friday, November 7, 2025. Winners will be notified by December 1, 2025. One image submission will be accepted per person, and the image must be taken in downtown Pittsfield. Entrants must fill out a Google form and email their photo to Downtown Pittsfield, Inc. Full contest rules and entry information can be found below.
Submission Guidelines:
*Image must be taken in downtown Pittsfield. Click here to view map of approximate boundaries of downtown Pittsfield.
*Image must be your original work.
*One image submission per person. No exceptions. Your first entry will be the only one considered for judging.
*Image should be submitted in the highest resolution possible.
*Entrants must fill out the following Google form and email their photo to Downtown Pittsfield, Inc. Please clearly state your name as you would like it to appear in your email and on the Google form. Google Form link: https://forms.gle/EjX4dwwM4LUj1CBBA
Upon submission of your photo, Downtown Pittsfield, Inc. will own your photo and retain the right to use your photo submission in our print and online materials and on social media. Downtown Pittsfield, Inc. also retains the right to share your photo submission with other organizations. All entrants retain the right to use their photos after they are submitted. Downtown Pittsfield, Inc. will give photo credit whenever possible.
The winners of the Pittsfield Photo Challenge will be decided by an esteemed panel of Pittsfield judges.