Orange County Fair

Orange County Fairgrounds, Wisner Avenue, Middletown, NY, USA 23 Jul 2026

Whiskey Crossing at Orange County Fair

Orange County Fair Speedway 27 Jul 2026

Middletown Summer Concert Series !

Festival Square 31 Jul 2026

Bridal Show Galleria at Crystal Run

Galleria at Crystal Run 7 Nov 2026

Season Closer Truck Meet

Orange County Fair Speedway 31 Oct 2026

Roman Holiday - Film

Paramount Theatre - Middletown 1 Aug 2026

The Marshall & Sterling Insurance Run 4 Downtown RETURNS in 2026 with Live Music from First Round

Run 4 Downtown Middletown 15 Aug 2026

Orange Open Golf Outing

West Hills Country Club 15 Sep 2026

3 Fore Tee Charity Golf Outing

Walkill Golf Course 3 Aug 2026

Tykes Tuesday Kids Bowling at Round1

Galleria at Crystal Run 18 Aug 2026

The Odyssey - Film

Paramount Theatre - Middletown 28 Jul 2026

Iron Cobra Returns to the Orange County Fair Main Stage!

Orange County Fair Speedway 28 Jul 2026

2026 Summer Concert Series ft Rich Pell Band

Run 4 Downtown Middletown 6 Aug 2026

Golf Tournament Fundraiser for Sammy G.

126 E Main St, Middletown, NY 14 Aug 2026

2026 Summer Concert Series ft Dog Party Band

29 W Main St, Middletown, NY 10940-5715, United States 14 Aug 2026

SIP-N-PAINT @ HOUSE OF BIRRIA FT BOTTOMLESS SANGRIA

House of Birria Tacos & Cantina 22 Aug 2026

2026 Summer Concert Series ft Jungle Love

29 W Main St, Middletown, NY 10940-5715, United States 31 Jul 2026

2026 Summer Concert Series ft The Specs

29 W Main St, Middletown, NY 10940-5715, United States 28 Aug 2026

The Spinners

Paramount Theatre - Middletown 7 Nov 2026

2026 Summer Concert Series ft Rachel Leeya

29 W Main St, Middletown, NY 10940-5715, United States 7 Aug 2026