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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.


Upon submission of your photo, Downtown Pittsfield, Inc. will own your photo and retain 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. Downtown Pittsfield, Inc. also retains the right to share all photo submissions 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.


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

Two Tickets to any Barrington Stage Company Mainstage Show in their 2020 Season

City Tote, Lametta Throw, and Stonewashed Linen Robe from The Outlet at Pine Cone Hill ($171 retail value)

$25 Gift Card to Eat on North

$25 Gift Card to TOWNSHIP FOUR | Floristry & Home

$25 Gift Card to The Marketplace Café

$35 Gift Certificate to Lipa’s Latina

Small matted print by artist Karen Jacobs

Pair of tickets to a production at The Whitney Center for the Arts

Berkshire Athenaeum Swag Bag with branded goodies (t-shirt, mug, pin, magnets, and a 1-year family membership to the Friends of the Berkshire Athenaeum)

Bottle of Hot Harry’s Hot Damn! (Hot) Sauce and Wimpy (Mild) Sauce


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

$25 Gift Card to Patrick’s Pub and a men’s or women’s T-shirt

$25 Gift Certificate to Peace Train Tees

$35 Gift Certificate to Berkshire Paint and Sip

$25 Gift Card to The Marketplace Café

Heart of the Berkshires tote from Dory & Ginger

Gift Certificate for a private tour of Herman Melville’s Arrowhead for up to 6 people

Pair of tickets to a production at The Whitney Center for the Arts

Bottle of Hot Harry’s Hot Damn! (Hot) Sauce and Wimpy (Mild) Sauce


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