Entertainment events in Pittsfield

• Fri, 27 Mar, 2026 - 07:30 PM

  Kristin Key: The Camp Kristin Tour

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

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

  The Lovin' Spoonful in Pittsfield

  The Colonial Theatre

  7+ Interested
• Sat, 14 Mar, 2026 - 08:00 PM

  Aquanett LIVE at Proprietor's Lodge

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

  139+ 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

  86+ Interested
• Sat, 21 Mar, 2026 - 08:00 PM

  Skeeter Creek At The Proprietor’s Lodge

  22 Waubeek Rd

  USD 23
• Sun, 15 Mar, 2026 - 12:00 PM

  St. Paddy's Day Party

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

  71+ 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

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

  SHYNE RETURNS TO Tavern at The A!!!!

  Tavern at the A

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

  SKI-BR Day w/ Pabst Blue Ribbon

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

  33+ Interested
• Sat, 04 Apr, 2026 - 07:00 PM

  Music Bingo Pt.2 w/ DJ Champ

  Tavern at the A

  29+ Interested
• Sat, 28 Mar, 2026 - 04:30 PM

  36th Annual Pittsfield Rotary Auction

  Berkshire Hills Country Club
• Sat, 30 May, 2026 - 07:30 PM

  Yacht Lobsters

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

  26+ Interested
• Thu, 26 Mar, 2026 - 07:00 PM

  SPINDLE (music bingo) w/ DJ Pup Daddy - Songs of the 2000s

  Thistle and Mirth

  4+ Interested
• Wed, 04 Mar, 2026 - 06:00 PM

  Jazz Vespers

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

  9+ Interested
• Sat, 21 Mar, 2026 - 07:00 PM

  Cards and Karaoke

  Country Club of Pittsfield - Berkshires

  USD 66