Downtown Pittsfield, Inc. is holding its 2nd annual 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 2020 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 2020 during First Fridays Artswalk (date to be determined).


Downtown Pittsfield, Inc. will accept photo submissions through November 5, 2019. Winners will be notified by December 6, 2019.


Downtown Pittsfield, Inc. retains the right to use all photo submissions in our print and online materials and on social media, as well as the right to display and advertise them during First Fridays Artswalk. All entrants retain the right to use their photos after they are submitted.


Thank you to the following businesses which have donated prizes so far: 

Peace Train Tees, Barrington Stage Company, Township Four, Hot Harry’s, Berkshire Paint and Sip, artist Karen Jacobs, Dory & Ginger, The Whitney Center for the Arts, Berkshire Athenaeum, Lipa’s Latina, The Outlet at Pine Cone Hill, Eat on North, Arrowhead, The Marketplace Cafe, and Patrick’s Pub


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.

*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.


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

  • Alex Reczkowski, Director, Berkshire Athenaeum
  • Cheryl Mirer, Executive Director, Downtown Pittsfield, Inc.
  • Gary R. Levante, SVP, Corporate Responsibility & Culture, Berkshire Bank and First Vice President, Downtown Pittsfield, Inc.
  • Jesse Cook-Dubin, Partner, Cohen Kinne Valicenti & Cook and President, Downtown Pittsfield, Inc.
  • Pittsfield Mayor Linda Tyer
  • Lindsey Schmid, 1Berkshire VP of Tourism & Marketing and DPI Board Member
  • Kimberly Gritman, Downtown Pittsfield, Inc. Marketing Coordinator
  • Michael J. Wynn, Chief of Police, Pittsfield Police Department
  • Representative Tricia Farley-Bouvier
  • Ty Allan Jackson, Founder – BIG HEAD BOOKS, READ OR ELSE
  • More judges to be announced!