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Downtown Pittsfield, Inc. is holding a photo challenge to find the photo that best captures why downtown 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!


The first-place winner, as determined by a panel of local judges, will have their photo featured in Pittsfield’s 2019 Downtown Guide and a Downtown Pittsfield, Inc. social marketing campaign. The first and second place winners will take home a prize package donated by local downtown businesses. In addition, select entries will be exhibited at Downtown Pittsfield, Inc. in 2019 during First Fridays Artswalk (date to be determined).


Downtown Pittsfield, Inc, will accept photo submissions through November 30th, 2018. Winners will be notified by January 7th, 2019. Downtown Pittsfield, Inc. retains the right to use all photo submissions in our marketing and on social media, as well as the right to display and advertise them during First Fridays Artswalk. All images used will be credited to their photographers and all entrants retain the right to use their photos after they are submitted.


Our first-place winner will receive a prize package to include:

  • $35 gift card to Patrick’s Pub
  • $50 gift card, comfy throw, and tote bag from The Outlet at Pine Cone Hill
  • $35 gift certificate to Berkshire Paint and Sip
  • A one-month membership to Berkshire Fitness and Wellness and a ½ hour personal training session with owner, Aimee Marshall
  • “Lunch with the State Senator” (for up to 4 people) with Senator Adam G. Hinds. Lunch can be in Pittsfield or at the State House – and if at the State House, it would include a State House tour.
  • $25 gift certificate to The Marketplace Cafe – Pittsfield
  • One 8″ X 8″ matted archival inkjet print by local artist Karen S. Jacobs
  • One acupuncture treatment by Dawn Meltzer, LICAC, acupuncturist in Lenox, MA.
  • One small painting by local artist Marney Shorr
  • 6 inch Carrot Cake from Mary’s Carrot Cake ($25 value)
  • 5 Original Cards by local artist Laura Didyk
  • Matted Berkshires print by local artist Sally Tiska Rice
  • Gift certificate to post flyers in Central Berkshire from “berkshireFLYER” ($50 value)
  • 2 tickets to a show in the 2019 season at the Whitney Center for the Arts


Our second-place winner will receive a prize package to include:

  • Two class passes ($20 value) to Berkshire Yoga Dance & Fitness
  • $25 gift certificate to The Marketplace Cafe – Pittsfield
  • One small painting on paper by local artist Peggy Morse
  • A beautiful scarf from Dory & Ginger
  • One gift certificate for a 60-minute Relaxation Massage Therapy at Intuitive Spirit Massage Therapy / Healing Arts
  • 5 Original Cards by local artist Laura Didyk
  • Matted Berkshires print by local artist Sally Tiska Rice


Submission Guidelines:

*Image must be taken in downtown Pittsfield. View map for 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.

*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.


The winners of the Pittsfield Photo Challenge will be decided by our esteemed panel of Pittsfield judges:

  • Senator Adam G. Hinds
  • Alexander Geller, Outreach Librarian, Berkshire Athenaeum
  • Cheryl Mirer, Executive Director, Downtown Pittsfield, Inc.
  • Pittsfield Mayor Linda Tyer
  • Lindsey Schmid, 1Berkshire Director of Marketing and DPI Board Member
  • Kimberly Gritman, Downtown Pittsfield, Inc. Marketing Coordinator
  • Michael J. Wynn, Chief of Police, Pittsfield Police Department
  • Nicholas Russo, Alta Planning & Design, DPI Board Member, “The Pittsfielder”
  • Noel Henebury, Sales Manager at Hotel on North, Pittsfield Artscape Chair and DPI Board Member
  • Representative Tricia Farley-Bouvier
  • Ty Allan Jackson, Founder – BIG HEAD BOOKS, READ OR ELSE