May is when both locals and visitors can’t wait to get outside — and when festival season ramps up.
The outdoor calendar is filled with music fairs like the Sing Us Home Festival and The Roots Picnic, foodie gatherings like the South 9th Street Italian Market Festival, and one of the nation’s first Pride events, New Hope Celebrates PrideFest.
Joining them are a plethora of neighborhood street festivals across the region, including the Girard Avenue Street Fest, Maifest on South Street and the Rittenhouse Row Spring Festival.
The May merriment doesn’t stop there, with more annual events including Fan Expo at the Pennsylvania Convention Center and the 40,000 athlete-strong Independence Blue Cross Broad Street Run.
Check out our guide to the biggest events and most awesome things to do in Greater Philadelphia in May 2026.
Note: This article is arranged chronologically by section.
‘ The preceding article may include information circulated by third parties ’
‘ Some details of this article were extracted from the following source www.visitphilly.com ’
