The Philadelphia Parallel Parking Association (PPPA) and the South Street Headhouse District are pleased to announce that the 2026 PPPA Championship will be held at Headhouse Plaza (2nd and South Street) on Saturday, October 3rd, from 1-4pm (rain date Saturday, October 10th, 1-4pm). Come see the best in the business battle it out to find out who the best parallel parker in Philly is. 20 contestants. 3 events. 1 winner. Park proud. More info here. Artwork by @drawjanedraws

Feel the groove and soak up the sound as the Philly Pops Little Big Band brings classic Motown and R&B favorites to Headhouse Plaza! This free outdoor performance fills the historic South Street Headhouse District with irresistible rhythms, soulful melodies, and the kind of energy that gets everyone moving. AstroTurf with lawn games will be rolled out to create a relaxed, picnic-style setting, so bring a blanket or chair, grab a bite, and settle in for an afternoon of live Motown music that brings the whole neighborhood together. 🧺🌞 Here’s the band’s rundown: 🎶 Philly Pops Rehearsal: 11:30AM-2PM 🎻 Settlement Music School Performances: 3PM 🎺 Philly Pops Performance: 3:45PM 🥁 Instrument Petting Zoo: 2:30-5PM Stop by Settlement Music School’s instrument petting zoo table, where kids can explore different sounds of the percussion family! 🪘🎵 This is a picnic you won’t want to miss! Come enjoy an afternoon of music, fun, and family-friendly activities. More info about the Philly Pops here.  A big thank-you to Settlement Music School for helping sponsor this event. We can’t wait to see you there! 🎉

Mark your calendars and get ready for Halloween on South Street! 🎃👻 Join us for a spooktacular day of Halloween fun featuring activities for all ages throughout the District! Get dressed up, grab your friends and family, and celebrate with us! Here’s what’s in store: 🎭 Halloween Costume Promenade 🚗 Trunk-or-Treat 🍬 Candy Crawl: Go trick-or-treating at shops throughout the District! 🍻 Boos-or-Brews: Enjoy Halloween drink specials at bars and restaurants throughout the District! 🎬 Rocky Horror Movie Screening at the TLA 🗓️ More details and event times coming soon! 

The South Street Holiday Night Market transforms the District into a festive, family-friendly celebration featuring a tree lighting, Santa’s arrival, live entertainment, local vendors, and seasonal food and drinks. Guests of all ages can enjoy holiday activities like crafts, gift shopping, photos with Santa, and interactive experiences that highlight community spirit and local businesses. More details about participating businesses, food trucks, and vendors to be announced soon!

Stay tuned for our 2027 SSHD event dates!