Entertainment events in Pittsfield

• Sat, 14 Mar, 2026 - 08:00 PM

  Aquanett LIVE at Proprietor's Lodge

  The Proprietor's Lodge - Lakefront Events, Dining & Venue

  114+ Interested
• Sat, 07 Feb, 2026 - 07:30 PM

  Rev Tor’s 14th Annual Dead of Winter Jam

  The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

  178+ Interested
• Sat, 09 May, 2026 - 07:00 PM

  The Lovin' Spoonful in Pittsfield

  The Colonial Theatre
• Fri, 30 Jan, 2026 - 06:00 PM

  Richmond Night at Balderdash

  Balderdash Cellars

  25+ Interested
• Sat, 24 Jan, 2026 - 09:00 PM

  Even It Up comes to The Parkside!!

  Parkside Restaurant

  96+ Interested
• Wed, 11 Feb, 2026 - 07:00 PM

  SPINDLE (music bingo) w/ DJ Pup Daddy - Awesome 80s

  Hot Plate Brewing Co.

  10+ Interested
• Sat, 14 Mar, 2026 - 07:30 PM

  Beyond The Wall Performs Dark Side of the Moon

  The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

  90+ Interested
• Sat, 31 Jan, 2026 - 05:00 PM

  2026 Brett Haas Racing Party

  Polish Falcon Club

  USD 10
• Sat, 14 Mar, 2026 - 12:00 PM

  SKI-BR Day w/ Pabst Blue Ribbon

  101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

  26+ Interested
• Sat, 14 Mar, 2026 - 12:00 PM

  DJ on the Deck Après Ski Party

  101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

  40+ Interested
• Tue, 20 Jan, 2026 - 02:00 PM

  Movie Afternoons | Screening of National Treasure

  1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201

  4+ Interested
• Tue, 27 Jan, 2026 - 02:00 PM

  Movie Afternoons | Screening of Mona Lisa Smile

  1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201

  5+ Interested
• Sat, 14 Mar, 2026 - 07:30 PM

  Dark Side of the Moon performed by Beyond the Wall

  Colonial Theatre

  41+ Interested
• Sat, 07 Feb, 2026 - 07:00 PM

  PHS Boys Basketball Music Bingo (CASH PRIZES!!)

  Tavern at the A

  148+ Interested
• Sat, 28 Mar, 2026 - 07:30 PM

  Rev Tor’s 30th Anniversary Jam

  The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

  47+ Interested