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

  131+ 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

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

  The Lovin' Spoonful in Pittsfield

  The Colonial Theatre
• 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

  112+ Interested
• Fri, 30 Jan, 2026 - 06:00 PM

  Richmond Night at Balderdash

  Balderdash Cellars

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

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

  Hot Plate Brewing Co.

  10+ 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

  30+ 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
• Sat, 14 Mar, 2026 - 07:30 PM

  Dark Side of the Moon performed by Beyond the Wall

  Colonial Theatre

  54+ Interested
• Sat, 07 Mar, 2026 - 08:00 PM

  SHYNE RETURNS TO Tavern at The A!!!!

  Tavern at the A

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

  PHS Boys Basketball Music Bingo (CASH PRIZES!!)

  Tavern at the A

  155+ 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

  57+ Interested
• Wed, 04 Feb, 2026 - 06:00 PM

  Jazz Vespers

  74 1st St, Pittsfield, MA, United States, Massachusetts 01201

  46+ Interested
• Sat, 30 May, 2026 - 07:30 PM

  Yacht Lobsters

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

  23+ Interested