You can now conveniently pay for parking in downtown Pittsfield on your phone. Download the Passport app from either the App Store of Google Play. 

Parking App
Google Play:

iTunes App

Downtown Parking Zones

Zone# 1012 – Zone A –Downtown Area - South Street, North Street, Park Square, Federal Street, Wendell Ave. Extension

Zone #1013 – Zone B – Berkshire Medical Center Area -  Wahconah Street

Zone #1014 –Zone C -  Municipal Parking Areas – Depot Street Parking Lot and McKay Street Parking Lot

The Sticker below are on all parking meters 
Parking Stickers