

“Where’s Winston?” Scavenger Hunt at First Fridays at Five
September 05, 2025Downtown Pittsfield, Inc. will present a one-night-only Back-to-School edition of “Where’s Winston?” during the September 5th First Fridays at Five. This Back-to-School themed scavenger hunt for images of Officer Winston, the Pittsfield Police Department’s comfort dog, will take place on Friday, September 5, from 5 to 7:45 pm. Game Cards will be available at the Downtown Pittsfield, Inc. tent in Dunham Mall at 100 North Street starting at 5 pm. The last Game Card will be redeemed at 7:55 pm. “Where’s Winston?” is for children aged 3 to 18 years old, and young children participating must be accompanied by a parent or guardian.
Every Winston will have a unique Back-to-School themed word with him. Find the hidden Winstons, write the words on the Where’s Winston? Game Card, and bring the Game Card to the Downtown Pittsfield, Inc. tent in Dunham Mall at 100 North Street to redeem for prizes.
All participants will get a Winston Sticker.
Children who find any 5 words will win a Winston Drawstring Bag while supplies last.
The first 10 children who find all 6 words and turn in their completed Game Card to the Downtown Pittsfield, Inc. tent in Dunham Mall will win a Winston plushie!


