Halloween season on South Street

It’s almost spooky season on South Street.

The South Street Headhouse District has a pair of Halloween events coming up in late October, bringing back its popular PumpkinFest while introducing a new Costume Crawl & Bar Bash.

On Oct. 28 from noon to 4 p.m., the South Street Headhouse District will host PumpkinFest 2023 at the Headhouse Shambles (2nd and Pine streets), celebrating the fall season in a fun and festive way. The event will feature an afternoon of family-friendly Halloween arts and crafts, copious amounts of candy, plus potions and bites from neighborhood businesses. 

Families can look for free pumpkin decorating, circus performances and a costume contest. The PumpkinFest costume contest will judge four categories including 5 and under, 6-10, 11 and over and families. PumpkinFest also coincides with trick-or-treating in the South Street Headhouse District, which is free to participate and open to anyone.

Don’t know the terrain? No problem. Physical and digital maps will be available to help guide trick-or-treaters on and around South Street, and participating businesses will have pumpkin signs in their windows. 

Guests can return to South Street for round two on Oct. 31 as the District will host its first-ever South Street Halloween Costume Crawl & Bar Bash. The event kicks off at 7 p.m. at 5th and South streets and ends at the Headhouse Plaza on 2nd and Lombard streets.

Join host Jarbeaux of The Bearded Ladies Cabaret as she leads a staggering spectacle of killer kweens, monster mashes and philthy Philadelphians down South Street. 

The Costume Crawl contest will also include four categories but they are not based on age although every participant must be over 21. Contestants will be judged on areas such as Spooky & Scary, Silly & Wacky, Sexy & Sultry and Pop & Trendy. Prizes include $1,000 of goodies from local district businesses. Although participants must be 21-plus, all are invited to join the Crawl. Contest registration is open through the Headhouse District’s website at southstreet.com, and participants are encouraged to sign up early to secure a spot.

In support of the Costume Crawl will be the inaugural Bar Bash. Haunt the bars, restaurants and shops on and around South Street all night long for haunting Halloween specials, deals and discounts. Participants in the Costume Crawl will receive exclusive access to several spooky specials.

The events are still a month away, but there are advantages to heading to South Street early. The trendy avenue is also a great place to purchase a Halloween costume, Shop Secondhand on South to celebrate sustainably or stand out from the crowd with a spectacular getup from South Street boutiques and stores.