On Saturday, October 3, hundreds of people stood at Headhouse Plaza to watch 14 drivers parallel park. Mario "One-Shot Mar" Zucca of West Mount Airy wore a red stuntman suit. Before the final round he opened the hatchback of his 2012 Mazda and let out a bunch of balloons, then went up and down the crowd firing fake parking tickets from a money gun. He won a trophy with a piece of curb on it and $76 for his next ticket.
This was the first Philadelphia Parallel Parking Association Championship, and nearly 900 people applied to compete. The event was a joke with a trophy. Its location was not. It was among the first big public events held next to the Head House since the fencing came down, and it is the sort of use the building was restored for.
What $1.625 Million Bought at Second and Pine
Construction fencing went up around parts of the site in March. By August 17, the New Market & Head House Conservancy said its $1.625 million renovation was complete. A City of Philadelphia grant secured by Councilmember Mark Squilla paid for the work. The plans came from John Milner Architects, a historic preservation firm. W.S. Cumby Construction, a family-owned builder that restores landmarks, did the work.
The list of work done is longer than most people would guess from the sidewalk:
- Repairs to the Head House roof
- Restored, repainted and lighted cupola woodwork
- Repointed brickwork, repainted shutters and new windows
- A renovated office inside the building
- A new ground-floor bathroom for special events
- Restoration of the historic clock and new clock faces
The Inquirer credits the clock to Isaiah Lukens. In a July 15 update, the Conservancy said faces had been installed on both sides of the cupola and the clock itself would go in within about a week.
The event bathroom is the least romantic item on that list, but it best explains what the project is for. A farmers market can run for four hours without one. A concert, a holiday market or a long fall afternoon of programming is easier with one.
Why the Conservancy Wanted More Than a Repair
The site is old enough that it shaped the street around it. The New Market dates to 1745. Second Street had to be made nearly three times wider to fit the wagons that crowded the shambles, the covered colonnade at the center of the market. By 1805 a head house had been built at the northern end as a firehouse. USHistory.org dates the building to 1803.
For years, the South Street Headhouse District leased the city-owned site for $1 a year and rented it out for weddings and the farmers market. The new Conservancy formed in 2025 to take over the landmark, its renovation, its special events and the weekly market. When the project was announced in May, Conservancy board member Paul Levy said plainly that the goal went beyond preservation. Levy was the founding CEO of the Center City District until he retired in 2024.
"We want to be able to program it as a regular space for families with kids, for events."
The commercial setting explains why. In the same article, the Inquirer listed the vacancies around the market. The former Second Street Wawa and CVS have both closed, and the 22,000-square-foot Abbotts Square retail space at Second and South has been empty since 2017. Levy summed up the project's theory this way: "Let's get some momentum going with the restoration of this historic site." Billy Penn reported in late August that South Street's commercial vacancy rate stood at 30% and that a proposed zoning remap for the corridor was still stalled.
So the restored building is meant to bring people to Second Street, and the fall calendar is the first real look at whether it can.
The Shambles Calendar, Date by Date
Nearly everything scheduled under the Shambles this fall comes from outside groups. Those include a citywide cider festival, the South Street District, The Food Trust and a parallel parking league founded this year. That pattern supports Levy's idea. Other organizers are choosing the space for their events.
- Every Sunday, 10 a.m. to 2 p.m. The Headhouse Farmers Market runs year-round at Second and Lombard. The Food Trust is putting together a Friends group to support the market and its programming. Pets other than service animals have not been allowed under the Shambles during market hours since March 2, 2025.
- Saturday, October 17, 11:30 a.m. to 5 p.m. Pops on the Plaza is free, set up picnic-style, and sponsored by Settlement Music School. The Philly Pops rehearses from 11:30 a.m. to 2 p.m., an instrument petting zoo runs from 2:30 to 5 p.m., Settlement students perform at 3 p.m., and the Philly Pops Little Big Band begins a Motown and R&B set at 3:45 p.m.
- Sunday, November 1, 3 to 7 p.m. Philly Cider Week ends with a market under the Shambles. PhillyVoice reports that it is free and open to all ages.
- Saturday, November 21, 4 to 8 p.m. The South Street Holiday Night Market comes to Headhouse Plaza with a tree lighting, Santa, live entertainment, local vendors and seasonal food and drink. Vendor details had not been posted when the event page went up.
Two items are missing on purpose. South Street Fall Fest, planned for September 26 with a children's pumpkin playground at Headhouse Plaza, was canceled because of weather. Halloween on South Street runs October 31 from 11 a.m. to 11 p.m. with a costume promenade, trunk-or-treat and candy crawl, but it covers the whole district rather than the plaza, and times for many activities were still to come.
November 1 Is When the Site Gets Its Longest Day
Of all the dates above, November 1 tests the restoration's purpose most directly. It is a Sunday, so the farmers market runs from 10 a.m. to 2 p.m. An hour after the market closes, Philly Cider Week's closing event starts in the same spot. PhillyVoice lists Pennsylvania cider, live music, local snacks, face painting and optional cider passports, with free entry and proceeds going to The Food Trust. The festival opens a week earlier, on October 25, with a kickoff for Pennsylvania cider at Pip's.
That is eight hours of programming on one block on one day, run by two groups, with the same nonprofit benefiting from both. Before the restoration, the Shambles mostly hosted the market and rented events. A day like this is what the event bathroom and the reworked building were designed to make easier. The cider festival's schedule page had not named participating cideries when it was checked, so the lineup is still unconfirmed.
What Phase One Left Unfinished
The restoration is finished, but the plan isn't. In May, the Conservancy said it was trying to raise another $500,000 for repainting, a new clock face, facade lighting, updated historical signs and cobblestone repairs. Some of that was later covered. The August update says neighbors' donations are helping pay to light the Head House facade and update the historical information panels at both ends of the block. No source confirms that the facade lights are on yet.
The next phase still needs money. The Conservancy wants to improve the walking surfaces so Sunday markets and other events are easier for everyone to get around, and to upgrade and maintain the landscaping and planters. It asks for contributions from $250 up to $25,000.
The building has also become a small commercial listing. The Conservancy is looking for a local professional services firm to lease the renovated 560-square-foot second-floor office. The asking rent is $30 per square foot, the space has year-round HVAC, a kitchenette and six windows, and the Conservancy prefers offers that include a civic contribution. A paying tenant upstairs would make the Head House a working building between events, which fits the same goal of keeping the block busy.
Not far away, the Society Hill Civic Association approved spending about $54,000 on a neighborhood traffic study by Dewberry Engineers. It covers Pine, Spruce, Third, Fifth and Lombard Streets. The Head House and Shambles run from Pine to Lombard, both of which are on that list, so the study's findings could affect how people get to events there.
Second Street's empty storefronts won't fill because of one restored cupola. Still, this fall the Shambles hosts a concert, a cider festival, a tree lighting and a farmers market every Sunday, nearly all organized by groups that picked the site on their own. If you own near Headhouse Square and want to know how a busier Second and Pine might affect your home's value, John Carfi and the team can give you a calm, specific read on your block. Get Your Home Valuation.
