How to celebrate Halloween with South Street Headhouse District

Halloween is right around the corner, but the South Street Headhouse District is celebrating this weekend by hosting its annual Pumpkinfest, which will take place this Saturday, Oct. 28, from noon to 4 p.m.

The family-friendly event (which will take over the Headhouse Shambles at 2nd and Pine streets) will feature themed arts and crafts, plenty of candy, different food and drink options from neighborhood businesses, free pumpkin decorating, circus performances, and a costume contest. The latter will include four categories: 5 and under, 6 to 10 years, 11 and over, and families.

And, as a release states, PumpkinFest also coincides with Trick-or-Treating in the South Street Headhouse District, which is free to participate (and anyone can attend.) To make it a bit easier, 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 as well.

Then on Halloween (Tuesday, Oct. 31), the District will kick off its inaugural South Street Halloween Costume Crawl & Bar Bash. The event, which features host Jarbeaux of The Bearded Ladies Cabaret, will kick off at 7 p.m. at 5th & South Street. Philadelphians can join in as the host leads “a staggering spectacle of killer kweens, monster mashes, and philthy Philadelphians down South Street”—aka a costume parade for adults, which ends at the Headhouse Plaza on 2nd and Lombard streets. 

The Stateside Vodka and TargetPark sponsored Crawl contest will include four categories: Spooky and Scary, Silly and Wacky, Sexy and Sultry, and Pop and Trendy. Prizes include $1,000 of goodies from district businesses, and participants must be 21+, (but all are invited to join the Crawl.) Contest registration is open now, and participants are encouraged to sign up early to secure a spot, the release also states.

After the Crawl, Philadelphians can also head to the Headhouse District’s Bar Bash, involving local businesses through specials, deals, and discounts—which participants in the Costume Crawl will receive exclusive access to. Those who are interested in participating can also shop for their costume at South Street boutiques and stores ahead of time, a full list is available online. 

For more information, Philadelphians can visit southstreet.com or follow the South Street Headhouse District on Instagram and watch the #MeetMeOnSouthStreet hashtag for more information on upcoming events, block parties, night markets, and more, the release finishes. Philadelphians can also follow South Street Headhouse District on Twitter, Facebook, LinkedIn, and TikTok.