PHILADELPHIA — With its cobblestone streets, historic architecture, and independent boutiques, Chestnut Hill already feels like the set of a holiday movie. Starting November 22, the neighborhood officially leans into that charm with the return of its annual Holidays on the Hill celebration.
Running through Christmas Day, the district-wide festival turns Germantown Avenue and its surrounding landmarks into a hub of festive activity, featuring everything from model trains and parades to exclusive tours of the area's most stately homes.
The Kick-Off Weekend (Nov 22)
The festivities begin on Friday, November 22, with two major neighborhood traditions:
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Circle of Trees: Held at the Woodmere Art Museum (9201 Germantown Avenue) at 5:30 p.m., this free community event is the official start of the season. Families can enjoy hot chocolate, cider, cookies, and festive music while kids receive goodie bags.
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Holiday Garden Railway: The beloved attraction at Morris Arboretum & Gardens opens for the season. Visitors can watch model trains navigate a quarter-mile of track through a landscape of natural materials and twinkling lights. The railway runs daily from 10 a.m. to 4 p.m. through December 30.
Shopping Under the Lights: Stag & Doe Nights
Chestnut Hill is bringing back its most popular shopping tradition: Stag & Doe Nights.
On Wednesdays (December 3, 10, and 17) from 5:00 p.m. to 9:00 p.m., the shops along Germantown Avenue will stay open late. The streets fill with holiday spirit as merchants offer complimentary refreshments, treats, and special promotions. It is the perfect opportunity to find one-of-a-kind handcrafted gifts while strolling the illuminated avenue.
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Pro-Tip: To make shopping stress-free, the neighborhood is offering free parking every Wednesday beginning November 29 through Christmas.
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Small Business Saturday: Shoppers can also get a head start on gifts during Small Business Saturday on November 29, supporting the independent boutiques that define the "Hill."
Parades and House Tours
The celebration continues into December with two marquee events:
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Annual Holiday Parade (Dec 6): The Chestnut Hill Community Association’s parade steps off at 9:00 a.m. from Rex and Germantown Avenues, marching down to the Market at the Fareway. It’s a classic small-town parade perfect for families.
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Holiday House Tour (Dec 13): For architecture lovers, this is the highlight of the season. From 10:00 a.m. to 4:00 p.m., guests can tour a curated selection of Chestnut Hill’s most beautiful historic homes, all decked out in professional holiday decor. Attendees can hop on an event trolley or take a self-guided tour at their own pace.
From the twinkling lights of the Arboretum to the bustling shops of Germantown Avenue, Chestnut Hill is poised to be Philadelphia's go-to destination for old-world holiday charm.
