Entertainment events in Middletown

• Sat, 20 Dec, 2025 - 09:00 PM

  DJ MACKDITTY @ The Switch Inn

  126 E Main St, Middletown, NY
• Sat, 20 Dec, 2025 - 07:00 PM

  Follow Suit at Aspire Brewing

  Aspire Brewing

  10+ Interested
• Fri, 19 Dec, 2025 - 07:00 PM

  Bonfire Winter Warmer: Live Music with Shades, Ugly Sweater Party, Cocktails, & More!

  4 South Street, Middletown, NY, United States, New York 10940

  55+ Interested
• Sat, 20 Dec, 2025 - 07:00 PM

  Candle Concert 3: Holiday Classics at United Church

  United Presbyterian Church

  Free
• Sat, 20 Dec, 2025 - 07:30 PM

  National Lampoon's Christmas Vacation

  Paramount Theatre of Middletown

  17+ Interested
• Sun, 22 Mar, 2026 - 08:00 PM

  Shades of HUNKS at Tapped (Middletown, NY) 03/22/26

  Tapped

  USD 18
• Sat, 20 Dec, 2025 - 07:00 PM

  Candle Concert 3🎄🎻🕯️Holiday Classics at United Church

  United Presbyterian Church of Middletown

  60+ Interested
• Sat, 20 Dec, 2025 - 11:00 AM

  Gingerbread house decorating party

  EPIK Athletics
• Sat, 03 Jan, 2026 - 07:00 PM

  Nailedshutt band at Aspire Brewery

  Aspire Brewing

  9+ Interested
• Sat, 13 Dec, 2025 - 03:00 PM

  Holiday Concert 🎶

  Galleria Mall At Crystal Run, Middletown NY

  17+ Interested
• Sat, 20 Dec, 2025 - 12:30 AM

  National Lampoons Christmas Vacation - Film - Middletown

  Paramount Theatre - Middletown
• Sat, 13 Dec, 2025 - 11:00 PM

  Mozey in New York

  The Meadows
• Sat, 10 Jan, 2026 - 01:00 PM

  Free SPELLERS Screening & Live Panel of Nonspeakers Q&A

  Middletown Thrall Library

  25+ Interested
• Sat, 14 Mar, 2026 - 06:00 PM

  THE GATHERING MASSES/A GRAND TRIBUTE TO OZZY

  The Zone at Clemson

  10+ Interested
• Sat, 13 Dec, 2025 - 08:00 PM

  Annual Christmas Light Show

  8 Shagbark St, Middletown, NY