Middletown Live Music Events

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

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

Run 4 Downtown Middletown 15 Aug 2026

2026 Summer Concert Series ft Rich Pell Band

Run 4 Downtown Middletown 6 Aug 2026

2026 Summer Concert Series ft Dog Party Band

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

2026 Summer Concert Series ft Rachel Leeya

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

20th Annual Marshall+Sterling Run 4 Downtown

17 North St, Middletown, NY 15 Aug 2026

Men of Soul

The Paramount Theatre (Middletown, NY) 25 Sep 2026

2026 Summer Concert Series Ft Alex Haines, Maxillian Mezetin & Martin Tuzo Trio

Run 4 Downtown Middletown 30 Jul 2026

2026 Summer Concert Series ft Lorely Chavez y su Fantasia Musical

29 W Main St, Middletown, NY 10940-5715, United States 4 Sep 2026

Iron Cobra Returns to Clemson Brothers Brewery!

The Zone at Clemson 7 Aug 2026

Live and Let Die - A Symphonic Tribute to Paul McCartney

The Paramount Theatre (Middletown, NY) 2 Oct 2026

The Spinners

The Paramount Theatre (Middletown, NY) 7 Nov 2026