Upcoming Middletown Events

Check out what's happening all around Middletown, NY

Whiskey Crossing at Orange County Fair

Mon, 27 Jul at 07:00 pm Orange County Fair Speedway

Caroline Rhea at Paramount Theatre - Middletown

 Fri, 05 Jun at 08:00 pm Paramount Theatre - Middletown

HUNKS The Show at Tapped (Middletown, NY) 06/22/26

 Mon, 22 Jun at 08:00 pm Tapped USD 18 to 68

Nexgen JDM vs Euro NY Meet

Sun, 17 May at 03:00 pm Friendly Acura of Middletown

Stand Up Comedy with Matt Lipari

 Sat, 27 Jun at 08:00 pm Clemson Bros. Brewery USD 20

Season Closer Truck Meet

 Sat, 31 Oct at 12:00 pm Orange County Fair Speedway

Memorial Day BBQ Featuring Sean Von Clauss @ The Switch Inn

 Mon, 25 May at 11:00 am 126 East Main St Middletown NY 10940

The Mandalorian and Grogu

 Fri, 22 May The Paramount Theatre (Middletown, NY)

2026 Relay For Life of Berks

 Sat, 30 May at 11:00 am Berks County Fairgrounds

New Beginnings Montessori School Stepping Up Ceremony

 Fri, 22 May at 10:00 am The Paramount Theatre (Middletown, NY)

WBAOSC Annual Golf Outing

Thu, 01 Oct at 11:30 am Walkill Golf Course

Historic Hoffman Lodge Paranormal Investigation | Middletown, NY

 Sat, 20 Jun at 07:00 pm 9 Courtland St USD 55

COMEDY NITE @ BREAK POINT NY

 Sat, 25 Jul at 09:00 pm 1 Galleria Dr USD 29 to 45

Vinyl Tap DEBUTS at Orange County Fair

Sat, 25 Jul at 05:00 pm 239 Wisner Ave, Middletown, NY 10940-2400, United States

Christmas Island Kids Camp

 Wed, 15 Jul at 09:00 am 160 Blumel Rd, Middletown, NY, United States, New York 10941

Tequila for Sammy @ The Switch Inn

 Sat, 13 Jun at 03:00 pm 126 E Main St, Middletown, NY

Code Red Operation 25

 Sat, 13 Jun at 05:00 pm The Paramount Theatre (Middletown, NY)

Plush, Major Moment, Mama Doom & Misfit Toys

 Fri, 14 Aug at 07:00 pm The Zone @ Clemson USD 23

The Beezly Experience Business Expo

Sun, 31 May at 02:00 pm Limelight Hall

2026 Northern Academy Commencement

 Fri, 29 May at 01:00 pm Paramount Theater Free

Skyline AKC May Trial

 Fri, 22 May at 07:00 am 120 Tetz Lane, 10941

The Bridal Experience | Luxury Bridal Show at Ettanaej Event Center

 Sat, 30 May at 12:00 pm 779 NY-211E #8 Free

Snow White & Moriondor at Tapped

Sat, 13 Jun at 07:00 pm Tapped

The Mandalorian and Grogu (Open Caption Showing)

 Wed, 27 May The Paramount Theatre (Middletown, NY)

Author-Thon @ Middletown Thrall Library

Sat, 06 Jun at 10:30 am Middletown Thrall Library

Brunch every Saturday & Sunday @ The Switch Inn

 Sun, 14 Jun at 11:00 am 126 East Main St Middletown NY 10940

I.H.O.P.E Women’s Conference 2026

 Fri, 22 May at 06:00 pm 130 Dolson Ave suite 201 Free

Inspire Foundation Golf Tournament

 Mon, 18 May at 08:30 am West Hills Country Club

Thrills & Chills Book Fair

 Sun, 12 Jul at 12:00 pm Aspire Brewing USD 18 to 77

Goshen Fire Department Golf Outing 2026

 Mon, 29 Jun at 09:00 am West Hills Country Club

RISE & BUILD WOMEN CONFERENCE

 Sat, 23 May at 09:00 am 510 M&M Rd Free

WMHDHA.org June CE

 Sat, 06 Jun at 10:00 am Orange County Community College USD 20 to 30

Iron Cobra Halloween Party at Clemson Brothers Brewery!

 Fri, 30 Oct at 08:00 pm The Zone at Clemson

Skyline June 6th & 7th UKI

 Sat, 06 Jun at 08:00 am 120 Tetz Lane, 10941

Middletown Workshop: Civil Service Careers & NY HELPS

 Tue, 09 Jun at 02:00 pm Orange County Career Center – Middletown Free

DEATH JOINS THE CLUB - Interactive Murder Mystery Matinee at Middletown Elks Lodge!

Sun, 28 Jun at 03:00 pm Middletown Elks Lodge #1097

Ladies Annual Paint Event

 Sat, 06 Jun at 02:00 pm Liberty Church Middletown

Praise Aerobics

 Sat, 13 Jun at 10:00 am Faith Temple Family Church USD 29

Friday Night with DJ MACKDITTY @ The Switch Inn

 Fri, 29 May 126 E Main St, Middletown, NY

Access: Charity Golf Event

 Mon, 01 Jun at 09:00 am West Hills Country Club

Iron Sharpens Iron Men's Brunch

 Thu, 18 Jun at 01:00 pm Faith Temple Family Church USD 23

Bibigirl Karaoke Reunion!

 Fri, 26 Jun at 09:00 pm Tapped

Skyline's Inaugural AKC Fast CAT May 30th & 31st

 Sat, 30 May at 06:00 am 120 Tetz Lane, 10941

Skyline NADAC May Trial

Sat, 16 May at 08:00 am 120 Tetz Lane, 10941

NYC Working Dogs Mock Trial

 Sat, 03 Oct at 07:00 am Middletown NY 10941

Iron Cobra Returns to Clemson Brothers Brewery!

 Fri, 07 Aug at 08:00 pm The Zone at Clemson

Keller Williams Hudson Valley United Career Opportunity Session

 Wed, 20 May at 06:00 pm 9 Bert Crawford Rd Free

THE ROCK FANTASY SPRING PINBALL OPEN

Sat, 06 Jun at 01:00 pm Rock Fantasy

Brews & Ballots at Tapped Middletown

 Mon, 18 May at 05:30 pm Tapped

Wing Wednesday @ The Switch Inn

 Wed, 27 May at 11:00 am 126 East Main St Middletown NY 10940

Beaded Quill at the Pocatello Ladies Auxiliary Christmas in July Event

 Sat, 18 Jul at 10:00 am Pocatello Ladies Auxiliary

June 2026 Seminar for Water and Wastewater Operators, PEs, and Non-Members

 Thu, 18 Jun at 08:00 am Town of Wallkill Golf Club USD 75 to 100

Town of Wallkill EMS New York, Free AHA Heartsaver CPR Training

 Tue, 14 Apr 22 Maltese Dr Free

Marketing 101 - Print Media

Tue, 19 May at 07:00 pm 28 North Street, Middletown, NY, United States, New York 10940

Lifeguard Recertification (6/15 & 6/16) Wallkill

 Mon, 15 Jun at 04:00 pm 270 Schutt Rd USD 35

Dine to donate fundraiser

 Tue, 16 Jun at 03:00 pm Mechanicstown

Trivia Night at Aspire Brewing

 Sun, 23 Mar at 06:30 pm Aspire Brewing Free

Meet and Greet with Jill Wilkins

Sat, 30 May at 09:30 am 351 east Main Street Middletown

Lifeguard Training Course (5/18-5/22) Wallkill

 Mon, 18 May at 04:00 pm 270 Schutt Rd USD 35

Lifeguard Recertification (5/17) Wallkill

 Sun, 17 May at 09:00 am 270 Schutt Rd USD 35

Sept. 2026 Seminar for Water and Wastewater Operators, PEs, and Non-Members

 Thu, 10 Sep at 08:00 am Town of Wallkill Golf Club USD 75 to 100

Nov 2026 Seminar for Water and Wastewater Operators, PEs, and Non-Members

 Thu, 12 Nov at 08:00 am Town of Wallkill Golf Club USD 75 to 100

October 2026 Grade A Compliant Lab Course. STOP!-See below before paying

 Tue, 20 Oct at 08:30 am Wallkill Town Hall USD 85

Self-Care City Scavenger Hunt–Based on Hot Habits Series: Middletown Area

 Thu, 03 Oct at 01:00 pm *Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED) USD 0 to 23

May 2026 Grade A Compliant Lab Course. STOP!-See below before paying

 Tue, 19 May at 08:30 am Wallkill Town Hall USD 85

August 2026 Grade A Compliant Lab Course. STOP!-See below before paying

 Tue, 25 Aug at 08:30 am Wallkill Town Hall USD 85

June 2026 Grade A Compliant Lab Course. STOP!-See below before paying

 Tue, 16 Jun at 08:30 am Wallkill Town Hall USD 85