May in Philadelphia is a transitional season where April showers become those mid-spring flowers before the heat of summer descends. With that comes the season to get outdoors for concerts, events, garden shows, carnivals, hiking, biking, sports and dining.

But above it all, May is the month that festival season kicks into high gear. Some of the best spring fests of all varieties return, including music festivals like Sing Us Home Festival, beer fests such as the Main Line Outdoor Beer & Wine Festival, foodie gatherings like Media’s Dining Under the Stars and one of the first major pride events of the year in the nation, New Hope Celebrates PrideFest.

Joining them is a plethora of seasonal street festivals celebrating neighborhoods across the region, including the Girard Avenue Street Fest, Roxborough Spring Fest, Made on American Street Festival, Kensington Derby and Arts Festival and the delicious South 9th Street Italian Market Festival.

The May merriment doesn’t stop there, with plenty of popular annual events to enjoy including the Fan Expo convention, the historic Devon Horse Show and the 35,000 athlete-strong Blue Cross Broad Street Run.

Level up your vacation or staycation extra special with a sumptuous hotel stay. Book the Visit Philly Overnight Package and get free hotel parking and choose-your-own-adventure perks, including tickets to Disney100: The Exhibition at The Franklin Institute, the Philadelphia Museum of Art, or the National Constitution Center and the Museum of the American Revolution. Or indulge in the new Visit Philly 3-Day Stay hotel package, which includes buy-two-get-one-free hotel nights at participating hotels.

Check out our guide to the biggest events and most awesome things to do in Greater Philadelphia in May 2024.

Note: This article is arranged chronologically by section.

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