Upcoming Middletown Events

Check out what's happening all around Middletown, NY

Harry Potter Party Orange County

 Sat, 06 Dec at 07:00 pm middletown, ny

Comedy Night

Sat, 22 Nov at 07:00 pm Pocatello/ Mount Hope Fire Co.

The City of Middletown Christmas Tree Lighting Ceremony & Parade

 Fri, 28 Nov at 06:00 pm Festival Square

“Encounter Night: Worship, Prayer & Power”

 Fri, 21 Nov at 07:00 pm 510 M&M Rd Free

An Evening of R&B Soul Music

 Sat, 15 Nov at 07:00 pm Clemson Bros. Brewery

Wellness Steep Tea Event at New Middletown

 Sat, 15 Nov at 10:00 am New Middletown Free

Wizard Fest Middletown 12/6 @ Clemson Bros Brewing

 Sat, 06 Dec at 08:00 pm Clemson Bros. Brewery USD 18 to 66

The 3oh! Rocking at Cosimo's Brick Oven

 Thu, 20 Nov at 06:30 pm Cosimos Brick Oven Ristorante & Bar

VETERANS APPRECIATION DAY DINNER

Sat, 15 Nov at 06:00 pm Hoffman Lodge No. 412 F&AM

Orange County 4-H Fun Night

 Fri, 21 Nov at 06:00 pm 18 Seward Ave, Ste 300, Middletown, NY, United States, New York 10940

Singles Mixer @ Tapped Restaurant in Middletown, NY

 Sat, 29 Nov at 06:00 pm Tapped NY

Singles Mixer (Speed Dating)/Couples Contest @Tapped in Middletown,NY

 Sat, 29 Nov at 06:00 pm Tapped USD 13 to 23

2025 Holiday Kissing Ball Workshop (Evening Session)

 Fri, 05 Dec at 06:00 pm 18 Seward Ave, Ste 300, Middletown, NY, United States, New York 10940

Advent in Action

 Sun, 23 Nov at 09:00 pm 58 W Main St, Middletown, NY, United States, New York 10940

Thanksgiving comedy show

Sat, 22 Nov at 09:30 pm Clemson Bros. Brewery

Orange County 4-H Horse Project Meetings

 Fri, 12 Dec at 06:30 pm 18 Seward Ave, Ste 300, Middletown, NY, United States, New York 10940

Friday Night with DJ MACKDITTY @ The Switch Inn

 Fri, 05 Dec at 09:00 pm 126 E Main St, Middletown, NY

Kids Night Out

Fri, 12 Dec at 06:30 pm The Center for Youth Programs, Liberty Street, Middletown, NY 10940

DJ MACKDITTY @ The Switch Inn

 Sat, 20 Dec at 09:00 pm 126 E Main St, Middletown, NY

11/29 2 pm Wreath Decorating Class

 Sat, 29 Nov at 02:00 pm Pierson's Farm

Resilient Port Jervis Community Action Group Meetings 2025

 Thu, 20 Nov at 06:30 pm 18 Seward Ave, Ste 300, Middletown, NY, United States, New York 10940

SATURDAY BRUNCH TRIVIA!

 Sat, 15 Nov at 12:00 pm Washington Heights

SATURDAY Holiday Wreath

 Sat, 29 Nov at 12:00 pm Terry Gardens USD 50

Fish & Chips Luncheon

 Sat, 22 Nov at 11:30 am 12 Depot Street, Middletown, NY 10940

Bridal Expo at Galleria at Crystal Run

 Sat, 24 Jan at 01:00 pm Galleria at Crystal Run Free

Holiday Fair & Bake Sale

 Sat, 22 Nov at 09:00 am 12 Depot St, Middletown, NY 10940

Toy Drive Giveaway

Fri, 05 Dec at 04:30 pm 81 Highland Ave, Middletown, NY

PINBALL FOR THE PETS

Sat, 15 Nov at 01:00 pm Rock Fantasy

Monday Night Football @ The Switch Inn

 Mon, 17 Nov at 08:00 pm 126 East Main St Middletown NY 10940

Winter Wonderland 2025

 Fri, 28 Nov at 05:00 pm 749 Route 17M, Middletown, NY, United States, New York 10940

FeteMent All Black

 Sat, 29 Nov at 08:00 pm 13 Railroad Ave USD 13 to 18

2025 Holiday Wreath Workshop

 Fri, 05 Dec at 02:00 pm 18 Seward Ave, Ste 300, Middletown, NY, United States, New York 10940

Sharon’s Private Group Wreath Decorating

Sun, 30 Nov at 10:00 am Pierson's Farm

Scene City Smackdown

 Fri, 14 Nov at 07:00 pm The Zone at Clemson

4-H Livestock Learning Night - Earn a YQCA Certification

 Tue, 25 Nov at 06:00 pm 18 Seward Ave, Ste 300, Middletown, NY, United States, New York 10940

Dine at Church Community Thanksgiving Dinner

 Sun, 23 Nov at 02:00 pm 40 Dunning Rd, Middletown, NY

WXAX Metal Night " THE FEAST... AFTER THE FEAST "

 Sat, 29 Nov at 06:00 pm The Zone at Clemson

A Smores Nutcracker at Paramount Theatre - Middletown

 Sun, 07 Dec at 03:00 pm Paramount Theatre - Middletown

2025 Santa Run

 Sat, 06 Dec at 01:00 pm 5 pocatello road, Middletown, NY

Ornament Paint & Sip- 2 wooden & 2 glass ornaments per ticket

 Thu, 11 Dec at 06:00 pm Tapped USD 30

VHV 3rd Annual Bowl-a-Thon

 Fri, 14 Nov at 05:30 pm Quinnz Pinz

4-H Livestock Learning Night - Marketing 101

 Tue, 16 Dec at 06:30 pm 18 Seward Ave, Ste 300, Middletown, NY, United States, New York 10940

A S'mores Nutcracker

 Sun, 07 Dec at 03:00 pm Paramount Theatre of Middletown

Aspire Greatness, King Trivia

 Sun, 16 Nov at 06:00 pm 600 N. Galleria Dr, Middletown, NY, United States, New York 10941

Iron Cobra Pre-Thankgiving Show!

 Fri, 14 Nov at 08:00 pm Quinnz Pinz

Designer Bag Bingo

 Sat, 06 Dec at 05:00 pm Orange County Fair Speedway Arena USD 40

12/13 10 am Wreath Decorating Class

 Sat, 13 Dec at 10:00 am Pierson's Farm

Shadows Of The 60s at Paramount Theatre - Middletown

 Sat, 22 Nov at 07:30 pm Paramount Theatre - Middletown

Hops & Hush - A Silent Reading Night

 Wed, 19 Nov at 07:00 pm 600 N. Galleria Dr, Middletown, NY, United States, New York 10941

Fall Festival at Oakridge Acres,

Sat, 15 Nov at 03:00 pm 155 Sands Rd Middletown NY

Black Friday Crystal Run Galleria Titi & Mimi's Delectable Delights

 Fri, 28 Nov at 09:00 am Galleria at Crystal Run

Jimmy Sturr at Paramount Theatre - Middletown

 Sat, 06 Dec at 03:00 pm Paramount Theatre - Middletown

Daybreak - The Music and Passion of Barry Manilow at Paramount Theatre - Middletown

 Fri, 12 Dec at 08:00 pm Paramount Theatre - Middletown

💜✨Sip, Learn & Build ✨💜

 Thu, 20 Nov at 06:00 pm 449 E Main St, Middletown, NY, United States, New York 10940

Daybreak - Tribute to Barry Manilow

 Thu, 11 Dec at 07:00 pm Paramount Theatre - Middletown

Grinch Event

 Sat, 06 Dec at 12:00 pm Middletown USD 39 to 58

Iron Cobra Christmas Party at Clemson Brothers with Co-Host Rock Fantasy!

 Fri, 19 Dec at 09:00 pm Clemson Bros. Brewery

Shadows of the 60s - A Tribute to Motown

 Fri, 21 Nov at 07:00 pm Paramount Theatre - Middletown

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

 Sun, 22 Mar at 08:00 pm Tapped USD 18 to 79

Skyline CPE Speedway Trial

 Fri, 14 Nov at 09:00 am 120 Tetz Lane, 10941

2025 Holiday Kissing Ball Workshop

 Fri, 05 Dec at 10:00 am 18 Seward Ave, Ste 300, Middletown, NY, United States, New York 10940

Nailedshutt band at Aspire Brewery

Sat, 03 Jan at 07:00 pm Aspire Brewing

🦃 Spark Curiosity & Connect: Educational Fun for All Abilities! 🌋

 Sun, 16 Nov at 11:00 am Galleria Mall, Crystal Run, Middletown, N.Y.

Jimmy Sturr Presents: The Magic of Christmas

Sat, 06 Dec at 03:00 pm Paramount Theatre of Middletown

Jillian’s private Group Wreath Decorating

Sun, 30 Nov at 02:00 pm Pierson's Farm

Switch Shirt Saturday @ The Switch Inn

 Sat, 06 Dec at 11:00 am 126 E Main St, Middletown, NY

Breakfast with Santa

 Sun, 14 Dec at 07:00 am 5 pocatello road, Middletown, NY

Skyline CPE Agility Trial

 Sat, 15 Nov at 07:00 am 120 Tetz Lane, 10941

Holiday Craft Fair @ The galleria at Crystal Run

 Sat, 22 Nov at 10:00 am Galleria at Crystal Run

One Night Only back at Cosimo's !

 Thu, 04 Dec at 06:30 pm Cosimos Brick Oven Ristorante & Bar

Country Night Line Dancing

Fri, 21 Nov at 07:00 pm 22 Cottage St, Middletown, NY

Holiday vendor and craft fair

 Sun, 30 Nov at 10:00 am Pocatello/ Mount Hope Fire Co.

JUST4U @ Middletown NY

 Sat, 15 Nov at 07:00 pm Clemson Bros. Brewery

49th Annual Orange County Home Show - OCC Middletown NY

 Fri, 13 Mar at 12:00 am 9 E Conkling Ave

Black Friday, November 28th at The Galleria @ Crystal Run

 Fri, 28 Nov at 09:00 am Galleria at Crystal Run

Wallkill East Rotary Turkey Trot 2025

 Thu, 27 Nov at 08:30 am Galleria at Crystal Run

Mozey in New York

 Sat, 13 Dec at 11:00 pm The Meadows

Parking Shadows Of The 60's

 Sun, 23 Nov Paramount Theatre - Middletown

Shadows Of The 60's

 Sun, 23 Nov Paramount Theatre - Middletown

Primitive Man, Buffalo Nichols, Great Falls in New York

 Tue, 16 Dec at 06:30 pm The Meadows

Local Birding in Spring and Summer

 Mon, 24 Nov at 05:30 pm SUNY_Orange Rcse Rowley Center

December ORC Monthly Member Meeting (Club Elections)

Wed, 10 Dec at 06:30 pm Destefano's Olde Erie

VENDOR / CRAFT FAIR

 Sun, 30 Nov at 10:00 am 5 Pocatello Rd, Middletown, NY

DAYBREAK - The Music & Passion of Barry Manilow

 Sat, 13 Dec at 01:00 am Paramount Theatre - Middletown

Fritay Night

 Sat, 15 Nov at 01:07 am RestoPam Haitian Restaurant

Local Birding in Fall and Winter

 Mon, 17 Nov at 05:30 pm SUNY_Orange Rcse Rowley Center

Bird Town Hall

 Mon, 08 Dec at 05:30 pm SUNY_Orange Rcse Rowley Center

Awesome Scavenger Hunt! - Middletown‘s Marvelous Mystery Hunt

 Fri, 20 Dec at 08:00 am 76-82 North St USD 15

Chester Monte's M**der Mystery - Middletown

 Tue, 04 Nov at 08:00 am Chester Monte's Murder Mystery - Middletown USD 23 to 60

Excelsior Ladder Co Middletown NY Fire Dept tricky tray

Sat, 15 Nov at 10:00 am 68 West Main St- Mulberry house senior center

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

 Tue, 24 Feb at 08:30 am Wallkill Town Hall USD 85

November 2025 Grade A Compliant Lab Course. STOP!-See below before paying

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