It’s a festive time of year anywhere in Philly—but in Old City specifically, locals get a jolly mix of both history and the holidays.
“Old City spent 2026 welcoming the world, and Historic Holidays is our invitation to come back and experience the neighborhood the way locals do,” says Job Itzkowitz, Executive Director of Old City District.
“This year’s programming is more interactive than ever, by design. When you spend a December afternoon here, you meet the owners, makers and chefs shaping this neighborhood, in the shops and restaurants they built. No online order can replicate that connection, and it’s what keeps people coming back long after the holidays.”
Historic Holidays officially kicks off with Small Business Saturday (Nov. 28). On that date, 300 independently owned businesses will offer specials, demonstrations, events and more. Philadelphians can walk around and catch artists weaving rugs in real time at Claudia Mills Rugs, explore Arch Enemy Arts’ annual 'Small Wonders 15' exhibition or head to Cassie’s Craft Coven’s for a free sticker-making station. There will also be discounts on fine jewelry and home goods, holiday card deals, complimentary gifts, seasonal treats and plenty more.
Next up, on Wednesday, Dec. 2, the area’s Tree Lighting will be in full swing at the Betsy Ross House. Starting at 6 p.m., there will be live musical performances, special guest speakers and a visit from Santa Claus before the lighting at 6:30 p.m. The following Saturday (Dec. 5) marks another signature event: the Holiday Shopping Sip & Stroll.
Celebrating its third year, the Sip & Stroll will once again transform Third Street (between Market and Arch) into a pedestrian-friendly hub of local shopping, festive drinks, live entertainment and plenty of surprises from 11 a.m. to 4 p.m. Visitors can browse an expanded lineup of independent shops, restaurants, galleries and attractions, or head to neighborhood cafés and bars for special offerings.
There’s also a new reason to check out the event in 2026, with the addition of the Holiday Shopping Sip & Stroll Passport. Participating Philadelphians can pick up a passport at event check-in (at the Betsy Ross House), where your first stamp comes with a complimentary hot cocoa. Then, locals can make their way through participating businesses to collect stamps, discover exclusive promotions and enjoy unique experiences. Those who complete their passport can drop it in Old City District’s Letters to Santa box for a chance to win a grand prize.
Highlights for the day also include an outdoor holiday market at Fringe Bar, floral pop-ups at The Papery, street performers and an expanded holiday shop at Ministry of Awe, complimentary cocktails at the Wyndham, specialty hot toddies at Khyber Pass Pub and a Disco Santa appearance at Ana Thorne.
Shoppers at the Sip & Stroll can additionally enjoy free gift wrapping at the Museum of the American Revolution, a designer gown sample sale at Bella Bridesmaids, dog treat bags at Opportunity Barks, and other offerings at local favorites like Positano Coast, Paradigm Gallery + Studio, Hitched, Oishii and more.
As a release notes, Old City's lineup on Dec. 5 also includes Elfreth's Alley's holiday fundraiser, Deck the Alley. During which, residents of America's oldest continuously inhabited street open their homes to the public alongside seasonal music, craft demonstrations and activities for kids. The event runs from 1 to 5 p.m., with timed entry available at 1, 2, 3 and 4 p.m.
The packed weekend will then cap off with a Community Menorah Lighting at the Betsy Ross House on Dec. 6. Presented in collaboration with the Old City Jewish Arts Center, the Hanukkah tradition will run from 4:30 to 5:30 p.m.
For a full schedule of Historic Holidays happenings in Old City, visit oldcitydistrict.org
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