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This past fall, Downtown Pittsfield, Inc. held a photo challenge to find the photo that best captures why downtown Pittsfield is the “Heart of the Berkshires”. Entrants were encouraged to capture photos that showcased the beauty and personality of downtown Pittsfield, keeping in mind the theme “Heart of the Berkshires”.


The first-place winner, as determined by a panel of local judges, is Susan Geller of Lenox. Her photo of this summer’s Tanglewood in the City at the Pittsfield Common has won her a prize package donated by local downtown businesses, and her photo will be featured in Pittsfield’s 2020 Downtown Guide and a Downtown Pittsfield, Inc. social marketing campaign.

Susan Geller photo. Tanglewood in the City

Our second-place winner, Terry Holland, will also take home a prize package donated by local downtown businesses. The winning photo is an aerial view of North Street.

Terry Holland photo. "North Street - Heart of the Berkshires"

Honorable Mentions: Shaun Muldowney, Gary Pratt, Maz Ghani, Elena V. Nuciforo, Meredyth Banahan, Lewis Reed, and Christy Butler

Shaun Muldowney photo. Onota Lake, early October 2019.
Gary Pratt photo. "Glorious Old Glory"
Maz Ghani photo. "Falling for Freedom"
Elena V. Nuciforo photo. "Urban Jungle"
Meredyth Banahan photo. "Rainbow"
Lewis Reed photo. "Park Square Aerial"
Christy Butler photo. "Fleeting feet in the foot race"

All photos that were entered into the contest will be exhibited at Downtown Pittsfield, Inc., 33 Dunham Mall, at a reception during a First Fridays Artswalk in 2020 (date to be determined).


The winners of the Pittsfield Photo Challenge were decided by an 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


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

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